Chiral Building Blocks

Vol. 9, o. 3 Chiral Building Blocks Features include: A Z Product Listings eterocyclic Building Blocks (S)-( )-Glycidol: chiral epoxide building block used in synthesis of many pharmaceuticals and natural products rganic Building Blocks

Introduction Introduction Asymmetric synthesis remains a challenge to synthetic chemists as the demand for enantiomerically pure compounds continues to increase. Whether the building blocks are used in the development of new and exciting chiral auxiliaries, ligands, or for obtaining advanced and enantiomerically enriched druglike molecules, research scientists continually need access to a vast array of novel chiral building blocks and architectures to achieve success. In this edition of ChemFiles, we have endeavored to provide a comprehensive listing of over 1000 chiral building blocks. Within each section of this issue, products are listed by increasing carbon content. Sigma-Aldrich is lists over 5000 chiral products for the successful construction of complex asymmetric architectures for a complete listing of products related to chiral chemistry and asymmetric synthesis, please visit us at sigma-aldrich.com/chiral. If you are unable to find a product for your research, Please Bother Us at mark.redlich@sial.com or contact your local Sigma-Aldrich office. If you are viewing the electronic version, simply select a category to jump to that section or activate your Adobe Bookmarks. You may also search by name, product number, molecular formula, or CAS registry number by using the find feature in Adobe (Ctrl+F in Windows or Command+F in a MacIntosh environment). Table of Contents eterocyclic Building Blocks...3 Furans...3 Indoles/Indolines/Indolizidines...5 Isoquinolines...6 Morpholines...6 xazoles/xazolines...7 Piperazines...7 Piperidines...8 Pyrans...10 Pyridines...10 Pyrrolidines...11 Quinuclidines...16 Thiophenes...16 thers...17 rganic Building Blocks...21 Acid alides...21 Alcohols...21 Aldehydes...28 Amides...29 About ur Cover Mark Redlich Product Manager Amines...30 Amino Alcohols...34 Aziridines...39 Carboxylic Acids...39 Cyanides/itriles...48 Epoxides...48 Esters...52 ydrocarbons...57 Isocyanates/Isocyanides...58 Ketones...59 Lactams/Lactones...62 Polyamines...64 Polyols...65 Protected Alcohols/Amines...68 Sulfonamides/Sulfinamides...69 Sulfonates/Sulfinates...70 thers...70 Risk and Safety Information...74 The image on our cover represents the three dimensional structure of (S)-( )-Glycidol. This chiral epoxide is a common building block used in synthesis of many pharmaceuticals and natural products. Aldrich Chemical Co., Inc. Sigma-Aldrich Corporation 6000. Teutonia Ave. Milwaukee, WI 53209, USA To Place rders Telephone FAX Vol. 9 o. 3 800-325-3010 (USA) 800-325-5052 (USA) Customer & Technical Services Customer Inquiries 800-325-3010 Technical Service 800-231-8327 SAFC 800-244-1173 Custom Synthesis 800-244-1173 Flavors & Fragrances 800-227-4563 International 414-438-3850 24-our Emergency 414-438-3850 Web Site sigma-aldrich.com Email aldrich@sial.com Subscriptions To request your FREE subscription to ChemFiles, please contact us by: Phone: 800-325-3010 (USA) Mail: Attn: Marketing Communications Aldrich Chemical Co., Inc. Sigma-Aldrich Corporation P.. Box 355 Milwaukee, WI 53201-9358 Email: sams-usa@sial.com International customers, please contact your local Sigma-Aldrich office. For worldwide contact information, please see back cover. ChemFiles are also available in PDF format on the Internet at sigma-aldrich.com/chemfiles. Aldrich brand products are sold through Sigma-Aldrich, Inc. Sigma-Aldrich, Inc. warrants that its products conform to the information contained in this and other Sigma-Aldrich publications. Purchaser must determine the suitability of the product for its particular use. See reverse side of invoice or packing slip for additional terms and conditions of sale. All prices are subject to change without notice. ChemFiles (ISS 1933 9658) is a publication of Aldrich Chemical Co., Inc. Aldrich is a member of the Sigma-Aldrich Group. 2009 Sigma-Aldrich Co. 2

eterocyclic Building Blocks Furans (S)-(+)-3 ydroxytetrahydrofuran, [86087 23 2] C 4 8 2 FW 88.11 296686 (R)-( )-3 ydroxytetrahydrofuran, [86087 24 3] C 4 8 2 FW 88.11 309753 (S)-(+)-5 xo-2 tetrahydrofurancarboxylic acid, [21461 84 7] C 5 6 4 FW 130.10 301469 (R)-Tetrahydrofuran-2 carbonitrile, 98.0% (GC, sum of enantiomers) [164472 78 0] C 5 7 FW 97.12 67948 C (R)-Tetrahydrofurfuryl alcohol, 98.0% (GC, sum of enantiomers) [22415 59 4] C 5 10 2 FW 102.13 89095 (S)-(+)-Tetrahydrofurfurylamine, [7175 81 7] C 5 11 FW 101.15 412945 2 eterocyclic Building Blocks (R)-(+)-Tetrahydro-3 furylamine p-toluenesulfonate salt, 99.0% (T) [111769 27 8] C 4 9 C 7 8 3 S FW 259.32 3 + S 3 C 3 (S)-(+)-Dihydro-5-(hydroxymethyl)- 2(3)-furanone, 95% [32780 06 6] C 5 8 3 FW 116.12 348902 (R)-( )-Tetrahydrofurfurylamine, [7202 43 9] C 5 11 FW 101.15 412937 2 09440 (R)-(+)-5 ydroxymethyl-2(5)- furanone, 97.0% (PLC, sum of enantiomers) [112837 17 9] C 5 6 3 FW 114.10 55673 (R)-( )-Dihydro-5-(hydroxymethyl)- 2(3)-furanone, [52813 63 5] C 5 8 3 FW 116.12 343544 (R)-(+)-Tetrahydro-2 furoic acid, (S)-( )-1-(2 Furyl)ethanol, 99.0% (GC, sum of enantiomers) [85828 09 7] C 6 8 2 FW 112.13 48188 Benzyl (S)-( )-tetrahydro-5 oxo- 3 furanylcarbamate, (S)-( )-5 ydroxymethyl-2(5)- furanone, [87392 05 0] C 5 8 3 FW 116.12 [87219 29 2] C 12 13 4 FW 235.24 Cbz [78508 96 0] C 5 6 3 FW 114.10 346861 (R)-( )-5 xo-2 tetrahydrofurancarboxylic acid, [53558 93 3] C 5 6 4 FW 130.10 310476 479292 (S)-( )-Tetrahydro-2 furoic acid, [87392 07 2] C 5 8 3 FW 116.12 527890 (S)-( )-Tetrahydrofuran-2 carboxamide, 419249 [3aR(3aα,4α,5β,6aα)]-( )-5- (Benzoyloxy)hexahydro-2 oxo-2cyclopenta[b]furan-4 carboxaldehyde, 95% [39746 01 5] C 15 14 5 FW 274.27 480517 C 5 9 2 FW 115.13 573310 2 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 3

(3aR)-(+)-Sclareolide, (+)-oe-lactol dimer, ( )-oe-lactol dimer, eterocyclic Building Blocks [564 20 5] C 16 26 2 FW 250.38 358002 ( )-Ambroxide, [6790 58 5] C 16 28 FW 236.39 379220 3C 3C C 3 3C 3C C 3 [87248 50 8] C 24 38 3 FW 374.56 254827 3C 3C C 3 3C C 3 3C [108031 79 4] C 24 38 3 FW 374.56 263907 3C C 3 C 3 3C C 3 Rare Chemical Library The Sigma-Aldrich Rare Chemical Library consists of over 140,000 unique chemical compounds, including: Private and academic collections released upon the researcher s retirement ne-time synthetic series from remote and obscure sources Products no longer available from the Sigma-Aldrich catalogs Plus synthetic analogs and precursors Available in standard sizes between 1mg and 1g Discovery CPR FREE! Request the Rare Chemical Library compound list on USB flash drive. Visit sigma-aldrich.com/rcl to find out more about this unique service. Rare Chemical Library items may also be packed to order through Discovery CPR. sigma-aldrich.com 4 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

Indoles/Indolines/Indolizidines (1S,6S,7R,8R,8aR)-1,6,7,8 Tetrahydroxyindolizidine, (3R)-( )-3-(1 Methyl-1-indol-3 yl) butyraldehyde, (3S)-(+)-3-(1 Methylindol-3 yl)- 3 phenylpropionaldehyde, [79831 76 8] C 8 15 4 FW 189.21 532673 (S)-(+)-2 Indolinemethanol, [27640 33 1] C 9 11 FW 149.19 523720 (S)-(+)-α-ydroxy-1,3 dioxo-2 isoindolinebutyric acid, C 13 15 FW 201.26 591882 (3S)-(+)-3-(1 Methyl-1-indol-3 yl)- 1 butanol, C 13 17 FW 203.28 592005 C 18 17 FW 263.33 591017 (3R)-( )-3-(methyl-1-indol-3 yl)- 3 phenylpropionic acid, C 18 17 2 FW 279.33 eterocyclic Building Blocks [48172 10 7] C 12 11 5 FW 249.22 409650 Methyl (3R)-( )-3-(1 methylindol- 3 yl)butanoate, C 14 17 2 FW 231.29 C 3 591734 Methyl (3S)-(+)-3-(methyl-1-indol- 3 yl)-3 phenylpropionate, (3S)-( )-3-(1 Methyl-1-indol-3 yl) butanenitrile, 591564 C 19 19 2 FW 293.36 C 13 14 2 FW 198.26 C (3S)-(+)-3-(1 Methylindol-3 yl)- 3 phenylpropionitrile, 591653 591785 C 18 16 2 FW 260.33 ( )-7 ctylindolactam V, ~90% (3S)-(+)-3-(1 Methyl-1-indol-3 yl)- 1 butyraldehyde, [406920 65 8] C 13 15 FW 201.26 C 3 591246 C 3 C [109346 66 9] C 25 39 3 2 FW 413.60 3C 3C C 3 C 3 1631 591343 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 5

Isoquinolines eterocyclic Building Blocks (S)-1,2,3,4 Tetrahydro-3 isoquinolinecarboxylic acid, 97.0% (T) [74163 81 8] C 10 11 2 FW 177.20 87437 (S)-( )-1,2,3,4 Tetrahydro-3 isoquinolinemethanol, [18881 17 9] C 10 13 FW 163.22 494186 (S)-( )-6,7 Dimethoxy-1,2,3,4 tetrahydroisoquinoline-3 carboxylic acid hydrochloride, [82586 62 7] C 12 15 4 FW 273.71 543527 3C 3C (S)-( )--tert-butyl-1,2,3,4 tetrahydro-3 isoquinolinecarboxamide, [149182 72 9] C 14 20 2 FW 232.32 493740 C 3 [3S-(3α,4aβ,8aβ)]--(tert-Butyl) decahydro-3 isoquinolinecarboxamide, [136465 81 1] C 14 26 2 FW 238.37 468916 Benzyl (S)-( )-1,2,3,4 tetrahydro- 3 isoquinolinecarboxylate p-toluenesulfonic acid salt, [77497 97 3] C 17 17 2 C 7 8 3 S FW 439.52 465062 3C S (R)-(+)-1-(4 Methoxybenzyl)- 1,2,3,4,5,6,7,8 octahydroisoquinoline, [30356 08 2] C 17 23 FW 257.37 539007 (S)-(+)-2-(Benzyloxycarbonyl)- 1,2,3,4 tetrahydro-3 isoquinolinecarboxylic acid, [79261 58 8] C 18 17 4 FW 311.33 465054 (S)-( )-1,2,3,4 Tetrahydro-α,α-diphenyl-3 isoquinolinemethanol, [140408 82 8] C 22 21 FW 315.41 496057 Cbz Morpholines (R)-4-3 morpholineacetic acid, 97.5% (PLC) (2S,3R)-(+)---6 oxo- 2,3 diphenylmorpholine, (2S,3R)-(+)--Z-6 oxo-2,3 diphenylmorpholine, [761460 03 1] C 11 19 5 FW 245.27 [112741 50 1] C 21 23 4 FW 353.41 [105228 46 4] C 24 21 4 FW 387.43 Cbz 669830 (S)-4-3 morpholineacetic acid, 97.5% (PLC) [839710 38 2] C 11 19 5 FW 245.27 669954 331813 (2R,3S)-( )---6 oxo- 2,3 diphenylmorpholine, [112741 49 8] C 21 23 4 FW 353.41 331856 (2R,3S)-( )--Z-6 oxo-2,3 diphenylmorpholine, [100516 54 9] C 24 21 4 FW 387.43 Cbz (S)-( )---5 benzyl-2 oxomorpholine, 331848 331872 [130317 10 1] C 16 21 4 FW 291.34 479926 6 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

xazoles/xazolines Methyl (S)-(+)-4,5 dihydro-2 phenyl-4 oxazolecarboxylate, 96% [78715 83 0] C 11 11 3 FW 205.21 516058 3C (4S,5S)-( )-2 Methyl-5 phenyl- 2 oxazoline-4 methanol, [53732 41 5] C 11 13 2 FW 191.23 187666 C 3 Methyl (4S,5S)-dihydro-5 methyl- 2 phenyl-4 oxazolecarboxylate, [82659 84 5] C 12 13 3 FW 219.24 292176 3C 3C (4S,5S)-( )-4,5 Dihydro-4 methoxymethyl-2 methyl-5 phenyloxazole, [52075 14 6] C 12 15 2 FW 205.25 3C Ethyl (2S)-(+)-2-[4-(6 chlorobenzoxazol-2 yloxy)phenoxy] propanoate, 95% [113776 20 8] C 18 16 5 FW 361.78 542776 eterocyclic Building Blocks 187658 Piperazines (R)-3 Methyl-2 ketopiperazine, 99.0% (GC) C 5 10 2 FW 114.15 (S)-(+)-2 Methylpiperazine, [74879 18 8] C 5 12 2 FW 100.16 397172 (S)-3-tert-Butyl-2,5 piperazinedione, 99.0% (C) [65050 07 9] C 8 14 2 2 FW 170.21 t-bu 51989 (S)-3 Methyl-2 ketopiperazine, 99.0% (GC) [78551 38 9] C 5 10 2 FW 114.15 (R)-( )-3 Isopropyl-2,5 piperazinedione, [143673 66 9] C 7 12 2 2 FW 156.18 C 3 20550 (R)-1-3 methylpiperazine, [163765 44 4] C 10 20 2 2 FW 200.28 73525 448362 674761 (R)-2 Piperazinecarboxylic acid dihydrochloride, 98.0% (T) [126330 90 3] C 5 10 2 2 2 FW 203.07 67176 2 (S)-3 Isopropyl-2,5 piperazinedione, 99.0% (PLC, sum of enantiomers) [16944 60 8] C 7 12 2 2 FW 156.18 59732 C 3 (S)-1-3 methylpiperazine, 98.0% (GC) [147081 29 6] C 10 20 2 2 FW 200.28 63207 C 3 (R)-( )-2 Methylpiperazine, [75336 86 6] C 5 12 2 FW 100.16 397164 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 7

eterocyclic Building Blocks (2S-cis)-( )-5 Benzyl-3,6 dioxo- 2 piperazineacetic acid, [5262 10 2] C 13 14 2 4 FW 262.26 421650 Piperidines (R)-(+)-3 ydroxypiperidine hydrochloride, (R)-( )-α-[[(4 Ethyl-2,3 dioxo-1 piperazinyl)carbonyl]amino]benzeneacetic acid, [63422 71 9] C 15 17 3 5 FW 319.31 472891 (R)-( )-3 Piperidinecarboxylic acid, C 3 (R)-( )-α-[[(4 Ethyl-2,3 dioxo-1 piperazinyl)carbonyl]amino]- 4 hydroxybenzeneacetic acid, [62893 24 7] C 15 17 3 6 FW 335.31 472905 (R)-1-3 hydroxypiperidine, 95% [198976 43 1] C 5 11 FW 137.61 410462 [25137 00 2] C 6 11 2 FW 129.16 656356 [143900 43 0] C 10 19 3 FW 201.26 687278 (S)-3 ydroxypiperidine hydrochloride, 98.0% (AT) [475058 41 4] C 5 11 FW 137.61 30169 (R)-( )-3 Aminopiperidine dihydrochloride, [334618 23 4] C 5 12 2 2 FW 173.08 666297 2 2 (S)-(+)-3 Aminopiperidine dihydrochloride, 96% [334618 07 4] C 5 12 2 2 FW 173.08 674109 2 2 (S)-(+)-3 Piperidinecarboxylic acid, [59045 82 8] C 6 11 2 FW 129.16 656364 (S)-(+)-2 Methylpiperidine, [3197 42 0] C 6 13 FW 99.17 522902 (R)-2 Piperidineethanol hydrochloride, 98.0% (GC) [787622 24 6] C 7 15 FW 165.66 670057 C 3 (S)-1-3 hydroxypiperidine, [143900 44 1] C 10 19 3 FW 201.26 687367 (R)-( )-3 Amino-1 -piperidine, 98.0% (TLC) [188111 79 7] C 10 20 2 2 FW 200.28 07858 (S)-(+)-3 Amino-1 -piperidine, 98.0% (TLC) [625471 18 3] C 10 20 2 2 FW 200.28 2 2 (S)-6 xo-2 piperidinecarboxylic acid, 95.0% (PLC) [34622 39 4] C 6 9 3 FW 143.14 36323 (S)-2 Piperidineethanol hydrochloride, 98.0% (GC) [786684 21 7] C 7 15 FW 165.66 670170 19929 (S)-3-(-amino)piperidine, 98.0% (TLC) [216854 23 8] C 10 20 2 2 FW 200.28 08601 8 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(S)-1-4 oxopiperidine- 2 carboxylic acid, 95% (R)-( )-1 Benzyl-3 hydroxypiperidine, (R)-(+)-1 Cbz-2 piperidinecarboxylic acid, C 11 17 5 FW 243.26 676322 (R)-1--4-oxopiperidine-2- carboxylic acid, C 11 17 5 FW 243.26 701130 8 (S)-1 -piperidine-3 carboxylic acid, [88495 54 9] C 11 19 4 FW 229.27 [91599 81 4] C 12 17 FW 191.27 455172 (S)-1-2 piperidineacetic acid, 99.0% (PLC) [159898 10 9] C 12 21 4 FW 243.30 669725 (R)-1-2 piperidineacetic acid, 99.0% (PLC) [351410 32 7] C 12 21 4 FW 243.30 [28697 09 8] C 14 17 4 FW 263.29 516376 D-(+)-Vesamicol hydrochloride [112709 60 1] C 17 25 FW 295.85 V104 Cbz ( )-Lobeline hydrochloride, [134 63 4] C 22 27 2 FW 373.92 141879 Ph eterocyclic Building Blocks 681229 (S)-(+)--()-2 methylpiperidine, [183903 99 3] C 11 21 2 FW 199.29 669628 Ethyl (S)---piperidine-3- carboxylate, 95% [191599 51 6] C 13 23 4 FW 257.33 8 (R)-( )-2 Piperidino-1,1,2 triphenylethanol, [213995 12 1] C 25 27 FW 357.49 522880 696404 647462 (S)-1 Benzyl-3 hydroxypiperidine, 97.0% (GC) (S)-( )-1 Cbz-2 piperidinecarboxylic acid, (S)-(+)-2 Piperidino-1,1,2 triphenylethanol, [91599 79 0] C 12 17 FW 191.27 [28697 11 2] C 14 17 4 FW 263.29 Cbz [869495 24 9] C 25 27 FW 357.49 499587 28964 647470 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 9

Pyrans eterocyclic Building Blocks (S)-6 Chloromethyl-5,6 dihydropyran-2 one, 98.0% (GC) [135999 61 0] C 6 7 2 FW 146.57 16749 (3aS,4R,6S,7aS)-Tetrahydro- 4 hydroxymethyl-6 methoxy-4furo[3,2-c]pyran-2(3)-one, [62158 33 2] C 9 14 5 FW 202.20 T8175 3C (3aS,4R,6R,7aS)-Tetrahydro- 4 hydroxymethyl-6 methoxy-4furo[3,2-c]pyran-2(3)-one, (R)-(+)-6 ydroxy-2,5,7,8 tetramethylchroman-2 carboxylic acid, [53101 49 8] C 14 18 4 FW 250.29 391913 3C C 3 C 3 (S)-( )-6 ydroxy-2,5,7,8 tetramethylchroman-2 carboxylic acid, [53174 06 4] C 14 18 4 FW 250.29 391921 3C C 3 C 3 (+)-Catechin hydrate, 96.0% (PLC, sum of enantiomers) [225937 10 0] C 15 14 6 x 2 FW 290.27 (Anh) 22110 2,3,4,6 Tetra--benzyl-α-D-glucopyranosyl trichloroacetimidate [74808 09 6] C 36 36 3 6 FW 685.03 524352 R R R = C 2 R C 3 R x2 [62210 98 4] C 9 14 5 FW 202.20 3C T8050 Pyridines (R)-α-Methyl-2 pyridinemethanol, 98.0% (GC) [27911 63 3] C 7 9 FW 123.15 41304 (S)-α-Methyl-2 pyridinemethanol [59042 90 9] C 7 9 FW 123.15 06368 (R)-(+)-α-Methyl-4 pyridinemethanol, [27854 88 2] C 7 9 FW 123.15 448532 3C (S)-( )-α-methyl-4 pyridinemethanol, [54656 96 1] C 7 9 FW 123.15 448540 3C (S)---1,2,3,6 tetrahydro-2 pyridinecarboxylic acid, 98.0% (PLC) [417726 36 4] C 11 17 4 FW 227.26 670286 (3S,5R,8aS)-(+)-exahydro-3 phe- nyl-5-oxazolo[3,2-a]pyridine- 5 carbonitrile, [106565 71 3] C 14 16 2 FW 228.29 642002 C (3R,5S,8aR)-( )-exahydro-3 phe- nyl-5-oxazolo[3,2-a]pyridine- 5 carbonitrile, [88056 92 2] C 14 16 2 FW 228.29 642118 C [2S-(2α,3β,8aβ)]-(+)-exahydro-3- (hydroxymethyl)-8a-methyl-2 phe- nyl-5-oxazolo[3,2-a]pyridin- 5 one, [116950 01 7] C 15 19 3 FW 261.32 388114 C 3 10 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

Pyrrolidines (R)-(+)-4 ydroxy-2 pyrrolidinone, [22677 21 0] C 4 7 2 FW 101.10 479160 (S)-( )-4 ydroxy-2 pyrrolidinone, [68108 18 9] C 4 7 2 FW 101.10 479179 (S)-(+)-3 Fluoropyrrolidine hydrochloride, [136725 53 6] C 4 8 F FW 125.57 637513 (R)-( )-3 Fluoropyrrolidine hydrochloride, [136725 55 8] C 4 9 F FW 125.57 637505 F F (S)-( )-3 Aminopyrrolidine, [128345 57 3] C 4 10 2 FW 86.14 540803 (R)-(+)-3 Aminopyrrolidine, [116183 82 5] C 4 10 2 FW 86.14 540781 (R)-( )-2-(Trifluoromethyl) pyrrolidine, [119618 29 0] C 5 8 F 3 FW 139.12 680087 (S)-(+)-2-(Trifluoromethyl) pyrrolidine, [119580 41 5] C 5 8 F 3 FW 139.12 665614 (R)-( )-5-(ydroxymethyl)- 2 pyrrolidinone, 2 2 CF3 CF3 (S)-(+)-2 Pyrrolidinemethanol, [23356 96 9] C 5 11 FW 101.15 186511 (R)-( )-2 Pyrrolidinemethanol, [68832 13 3] C 5 11 FW 101.15 281697 (R)-( )-1 Methyl-3 pyrrolidinol [104641 60 3] C 5 11 FW 101.15 647241 (S)-(+)-1 Methyl-3 pyrrolidinol, 95% [104641 59 0] C 5 11 FW 101.15 573337 C 3 (S)-(+)-2-(Aminomethyl)pyrrolidine, eterocyclic Building Blocks (S)-3 Pyrrolidinol, 97.0% (GC, sum of enantiomers) [100243 39 8] C 4 9 FW 87.12 56437 (R)-3 Pyrrolidinol, [66673 40 3] C 5 9 2 FW 115.13 366358 (S)-5-(ydroxymethyl)- 2 pyrrolidinone, [17342 08 4] C 5 9 2 FW 115.13 [69500 64 7] C 5 12 2 FW 100.16 422886 cis-3 Azabicyclo[3.1.0]hexane- 2 carboxylic acid, 2 [22255 16 9] C 6 9 2 FW 127.14 [2799 21 5] C 4 9 FW 87.12 382981 (R)-( )-3 Pyrrolidinol hydrochloride, [104706 47 0] C 4 9 FW 123.58 430722 366366 (R)-( )-2 Methylpyrrolidine [41720 98 3] C 5 11 FW 85.15 679097 (S)-(+)-2 Methylpyrrolidine, 90% [59335 84 1] C 5 11 FW 85.15 649147 391190 Methyl (S)-(+)-2 pyrrolidone- 5 carboxylate, [4931 66 2] C 6 9 3 FW 143.14 463396 3C Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 11

eterocyclic Building Blocks -[(2S)-2 Pyrrolidinylmethyl]-trifluoromethanesulfonamide, 98.5% (T) [782495 18 5] C 6 11 F 3 2 2 S FW 232.22 689017 (2R,5R)-( )-trans-2,5 Dimethylpyrrolidine, 97.0% (GC) [62617 70 3] C 6 13 FW 99.17 41566 (R)-(+)-3-(Dimethylamino) pyrrolidine, 95% S CF3 3C C 3 (S)-( )-2-(Methoxymethyl)- 1 pyrrolidinecarboxaldehyde, [63126 45 4] C 7 13 2 FW 143.18 277061 (S)-( )-2 Aminomethyl-1 ethylpyrrolidine, 96% [22795 99 9] C 7 16 2 FW 128.22 647446 (R)-(+)-2-Aminomethyl-1- ethylpyrrolidine, 90% 2 8 (S)-(+)---3 pyrrolidinol, [101469 92 5] C 9 17 3 FW 187.24 634786 (R)-(+)-1-3 aminopyrrolidine, [147081 49 0] C 9 18 2 2 FW 186.25 644064 (S)-( )-1-3 aminopyrrolidine, 95% 2 [132958 72 6] C 6 14 2 FW 114.19 3C [22795 97 7] C 7 16 2 FW 128.22 681709 C 3 2 [147081 44 5] C 9 18 2 2 FW 186.25 634794 2 656712 (S)-( )-3-(Dimethylamino) pyrrolidine, [132883 44 4] C 6 14 2 FW 114.19 656704 (R)-(+)-1 Amino-2-(methoxymethyl)pyrrolidine, 96% [72748 99 3] C 6 14 2 FW 130.19 281581 (S)-( )-1 Amino-2-(methoxymethyl)pyrrolidine, 95% [59983 39 0] C 6 14 2 FW 130.19 281573 3C 2 2 (S)-( )--(Trifluoroacetyl) pyrrolidine-2 carbonyl chloride solution [36724 68 2] C 7 7 F 3 2 FW 229.58 F3C (S,S)-2,2 -Bipyrrolidine D-tartrate trihydrate, 32 C 8 16 2 C 4 6 6 3 2 FW 344.36 688746 (S,S)-(+)-2,5 Bis(methoxymethyl) pyrrolidine, 97.0% (GC, sum of enantiomers) [93621 94 4] C 8 17 2 FW 159.23 15022 3C Butyl (S)-( )-2 pyrrolidone- 5 carboxylate, [4931 68 4] C 9 15 3 FW 185.22 440329 (R)-( )---3 pyrrolidinol, [109431 87 0] C 9 17 3 FW 187.24 532169 8 C 3 (R)-3-(-amino)pyrrolidine, 98.0% (TLC) [122536 77 0] C 9 18 2 2 FW 186.25 56308 (S)-3-(-amino)pyrrolidine, 98.0% (TLC) [122536 76 9] C 9 18 2 2 FW 186.25 52927 --4,4 difluoro-l-proline, [203866 15 3] C 10 15 F 2 4 FW 251.23 687340 --4 oxo-l-proline, [84348 37 8] C 10 15 5 FW 229.23 681202 F F 248509 12 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

--trans-4 fluoro-l-proline, (R)-(+)-1 Benzyl-3 pyrrolidinol, (S)-(+)-1 Benzyl-3 aminopyrrolidine, [203866 14 2] C 10 16 F 4 FW 233.24 687332 F --cis-4 fluoro-l-proline, [203866 13 1] C 10 16 F 4 FW 233.24 687324 F (R)-(+)-1-2 pyrrolidinecarbonitrile, [101930 07 8] C 11 15 FW 177.24 366935 (S)-( )-1 Benzyl-3 pyrrolidinol, [101385 90 4] C 11 15 FW 177.24 366943 [114715 38 7] C 11 16 2 FW 176.26 536598 (R)-( )-1 Benzyl-3 aminopyrrolidine, 95% [114715 39 8] C 11 16 2 FW 176.26 536601 2 2 eterocyclic Building Blocks C 10 16 2 2 FW 196.25 C 647233 (S)-( )-1-2 pyrrolidinecarbonitrile, [228244 04 0] C 10 16 2 2 FW 196.25 542091 (R)-2-(Azidomethyl)-1 pyrrolidine, 95% (PLC) [259537 91 2] C 10 18 4 2 FW 226.28 670006 (S)-2-(Azidomethyl)-1 pyrrolidine, 95% (PLC) [168049 26 1] C 10 18 4 2 FW 226.28 669881 (S)---2 methylpyrrolidine, 95% [137496 71 0] C 10 19 2 FW 185.26 687588 C 3 3 C 3 [163439 82 5] C 11 15 2 FW 193.24 37034 (3R,4R)-( )-1 Benzyl-3,4 pyrrolidinediol, 97.0% (PLC, sum of enantiomers) (3S,4S)-(+)-1 Benzyl-3,4 pyrrolidinediol, 97.0% (PLC, sum of enantiomers) [90365 74 5] C 11 15 2 FW 193.24 52057 1-(p-Tosyl)-(R)-( )-3 pyrrolidinol, [133034 00 1] C 11 15 3S FW 241.31 532150 S C 3 (R)-( )-2-(Anilinomethyl)pyrrolidine, [68295 45 4] C 11 16 2 FW 176.26 510505 --4-oxo-L-proline methyl ester, [102195 80 2] C 11 17 5 FW 243.26 702498 --trans-4-fluoro-l-proline methyl ester, [203866 18 6] C 11 18F 4 FW 247.26 702412 (S)-( )-1-3 acetamidopyrrolidine, [114636 37 2] C 11 20 2 3 FW 228.29 665088 (R)-(+)-1-3 acetamidopyrrolidine, F 8 C 3 8 [550371 67 0] C 11 20 2 3 FW 228.29 C 3 665061 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 13

(S,S)---2,5 dimethylpyrrolidine, 95% (R)-(+)-1 Benzylpyrrolidine-2 methanol, 95.0% (GC) (1S,2R)-1 Phenyl-2-(1 pyrrolidinyl)- 1 propanol, eterocyclic Building Blocks C 11 21 2 FW 199.29 688525 3C (S)-1-[(1 Methyl-2 pyrrolidinyl) methyl]piperidine, [84466 85 3] C 11 22 2 FW 182.31 446351 (R)-( )-1 Cbz-3 pyrrolidinol, 95% [182076 49 9] C 12 17 FW 191.27 68416 (1 R,3R)-(+)-1-(1 -Phenylethyl)- 5 oxo-3 pyrrolidinecarboxylic acid, [99735 43 0] C 13 15 3 FW 233.26 3C [56571 91 6] C 13 19 FW 205.30 548979 (S)-( )-1-(2 Methoxybenzoyl)-2- (methoxymethyl)pyrrolidine, [102069 84 1] C 14 19 3 FW 249.31 348368 C 3 [100858 33 1] C 12 15 3 FW 221.25 654655 Cbz 534366 (S)-( )-1-(2 Methoxybenzoyl)- 2 pyrrolidinemethanol, (R)---2 phenylpyrrolidine [174311 02 5] C 15 21 2 FW 247.33 (S)-(+)-1 Cbz-3 pyrrolidinol, 95% [100858 32 0] C 12 15 3 FW 221.25 654663 (S)-(+)-5-(ydroxymethyl)- 2 pyrrolidinone p-toluenesulfonate, 95% [51693 17 5] C 12 15 4S FW 269.32 444537 3C S Cbz (R)-( )-1 Cbz-3 aminopyrrolidine, C 12 16 2 2 FW 220.27 660078 Cbz (S)-(+)-1 Cbz-3 aminopyrrolidine, C 12 16 2 2 FW 220.27 660051 Cbz 2 2 [102069 83 0] C 13 17 3 FW 235.28 345628 (R)-(+)-1-(2 Methoxybenzoyl)- 2 pyrrolidinemethanol, [207511 15 7] C 13 17 3 FW 235.28 345598 (R)-(+)-1 Benzyl-3 acetylaminopyrrolidine, [114636 33 8] C 13 18 2 FW 218.29 536628 (1R,2S)-1 Phenyl-2-(1 pyrrolidinyl)- 1 propanol, [127641 25 2] C 13 19 FW 205.30 545481 685291 (S)-( )-1 Benzyl-3-(-amino) pyrrolidine, C 16 24 2 2 FW 276.37 649988 (R)-(+)-1 Benzyl-3-(-amino) pyrrolidine, [131878 23 4] C 16 24 2 2 FW 276.37 649961 (R)-(+)-2-(Fluorodiphenylmethyl) pyrrolidine, [352535 00 3] C 17 18 F FW 255.33 552550 F 14 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(S)-( )-2-(Fluorodiphenylmethyl) pyrrolidine, [274674 23 6] C 17 18 F FW 255.33 552569 (S)-( )-α,α-diphenyl-2 pyrrolidinemethanol, [112068 01 6] C 17 19 FW 253.34 552526 Benzyl (S)-( )-2-(1 pyrrolidinylcarbonyl)-1 pyrrolidinecarboxylate, [50888 84 1] C 17 22 2 3 FW 302.37 F Cbz (R)-( )-1 Fmoc-3 pyrrolidinol, 95% [215178 39 5] C 19 19 3 FW 309.36 654639 Fmoc (S)-(+)-1 Fmoc-3 pyrrolidinol, 95% [215178 38 4] C 19 19 3 FW 309.36 654647 Methyl (2S)-( )-2-(hydroxydiphenylmethyl)-1 pyrrolidinecarboxylate, [352535 68 3] C 19 21 3 FW 311.37 554448 3C Fmoc (S)-(+)-5-(Trityloxymethyl)- 2 pyrrolidinone, [105526 85 0] C 24 23 2 FW 357.44 374113 (S)-(+)---3--Fmoc-aminopyrrolidine, [307531 88 0] C 24 28 2 4 FW 408.49 651559 (R)-( )---3--Fmoc-aminopyrrolidine, [352530 40 6] C 24 28 2 4 FW 408.49 Fmoc Fmoc eterocyclic Building Blocks 462403 650919 Discover Super Silyl Protecting Groups Tris(trimethylsilyl)silane (360716) won the Fluka Reagent of the Year award in 1990 for its use as an alternative to tributylstannane (Bu 3 Sn) in radical reactions. Currently, the tris(trimethylsilyl)silyl (TTMSS, or supersilyl) group is being utilized in carbon carbon-bond forming reactions, where the researcher can take advantage of its unique reactivity that arises from its electronic properties and large steric bulk. Professor isashi Yamamoto has employed supersilyl enol ethers in a variety of efficient one-pot sequential reactions. Sigma-Aldrich is pleased to offer acetaldehyde supersilyl enol ether (698180) and other tris(trimethylsilyl)silyl reagents that allow you to use the supersilyl protecting group in your research. TTMSS (2.2 equiv) + TMS TMS Si TMS 360716 Tf 2 (0.05 mol %) C 2 2, 1 h TMS TMS Si TMS 409405 TTMSS TTMSS 75% syn:anti >95/5 TTMSS 698180 Boxer, M. B.; Yamamoto,. J. Am. Chem. Soc. 2006, 128, 48. For product-related inquiries, please contact our Technical Services department at 800-231-8327 (USA) or aldrich@sial.com. sigma-aldrich.com Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 15

Quinuclidines eterocyclic Building Blocks (R)-( )-3 Quinuclidinol hydrochloride, [42437 96 7] C 7 13 FW 163.65 532908 (S)-( )-3 Aminoquinuclidine dihydrochloride, [119904 90 4] C 7 14 2 2 FW 199.12 415723 2 2 (R)-(+)-3 Aminoquinuclidine dihydrochloride, [123536 14 1] C 7 14 2 2 FW 199.12 415715 2 2 (2R,4S,5R)-2 Aminomethyl-5 ethylquinuclidine, 95.0% (GC) [475160 61 3] C 10 20 2 FW 168.28 39867 2 3C (R)-( )-3 Quinuclidinyl benzilate [62869 69 6] C 21 23 3 FW 337.41 C003 Ph Ph Thiophenes (1R)-1-(2 Thienyl)ethanol, 98.5% (GC) -(R)-2-thienylglycine, 8 -(R)-3-thienylglycine, 8 [86527 10 8] C 6 8 S FW 128.19 S C 3 [74562 03 1] C 11 15 4S FW 257.31 S [33130 97 1] C 11 15 4S FW 257.31 S 06674 711861 711896 (1S)-1-(2 Thienyl)ethanol, 98.5% (GC) -(S)-2-thienylglycine, 8 -(S)-3-thienylglycine, 8 [27948 39 6] C 6 8 S FW 128.19 00791 S [40512 56 9] C 11 15 4S FW 257.31 711853 S C 11 15 4S FW 257.31 711888 S 16 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

thers D-ydroorotic acid, [5988 53 4] C 5 6 2 4 FW 158.11 537306 (1S,4S)-(+)-2,5 Diazabicyclo[2.2.1] heptane dihydrobromide, [132747 20 7] C 5 10 2 2Br FW 259.97 473006 (2R,5S)-2 Trichloromethyl-3 oxa- 1 azabicyclo[3.3.0]octan-4 one, 98.0% (AT) [97538 67 5] C 7 8 3 2 FW 244.50 3C 2Br (S)-1,4 Benzodioxane-2 carboxylic acid, 97.0% (GC, sum of enantiomers) [70918 54 6] C 9 8 4 FW 180.16 12351 Sepiapterin [17094 01 8] C 9 11 5 3 FW 237.22 S154 3C D-(+)-eopterin, 97.5% (PLC, sum of enantiomers) [2009 64 5] C 9 11 5 4 FW 253.21 2 2 (3S-cis)-(+)-2,3 Dihydro-3 isopropyl-7a-methylpyrrolo[2,1-b]oxazol-5(7a)-one, [116910 11 3] C 10 15 2 FW 181.23 458554 C 3 3C C 3 (3S-cis)-(+)-Tetrahydro-3 isopropyl- 7a-methylpyrrolo[2,1-b]oxazol-5 (6)-one, 95% [98203 44 2] C 10 17 2 FW 183.25 334235 3C C 3 (1S,4S)-( )-2-2,5 diazabicyclo [2.2.1]heptane, 95% eterocyclic Building Blocks 42134 (+)-6 Aminopenicillanic acid, 96% [551 16 6] C 8 12 2 3 S FW 216.26 A70909 2 S C 3 C 3 3386 (R)-2,5 Dihydro-3,6 dimethoxy- 2 isopropylpyrazine, 97.0% (GC) [109838 85 9] C 9 16 2 2 FW 184.24 3C C 3 C 3 C 3 [113451 59 5] C 10 18 2 2 FW 198.26 473049 ( )-p-bromolevamisole oxalate, (R)-(+)-1,2 Dithiolane-3 pentanoic acid, [1200 22 2] C 8 14 2S 2 FW 206.33 579602 S S (R)-1,4 Benzodioxane-2 carboxylic acid, 97.0% (GC, sum of enantiomers) [70918 53 5] C 9 8 4 FW 180.16 12348 37286 (S)-2,5 Dihydro-3,6 dimethoxy- 2 isopropylpyrazine, 97.0% (GC) [78342 42 4] C 9 16 2 2 FW 184.24 37289 3C C 3 C 3 (3R-cis)-( )-2,3 Dihydro-3 isopropyl-7a-methylpyrrolo[2,1-b]oxazol-5(7a)-one, [302911 94 0] C 10 15 2 FW 181.23 C 3 C 3 Br [62284 79 1] C 11 11Br 2S C 2 2 4 FW 373.22 190047 S (1S,4S)-( )-2-(4 Chlorophenyl)- 2,5 diazabicyclo[2.2.1]heptane hydrobromide [308103 51 7] C 11 13 2 Br FW 289.60 473391 Br C 3 458546 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 17

(1S,4S)-( )-2-(3 Fluorophenyl)- 2,5 diazabicyclo[2.2.1]heptane hydrobromide (1S,4S)-(+)-2 Benzyl-2,5 diazabicyclo[2.2.1]heptane dihydrobromide, (3R-cis)-( )-2,3 Dihydro-7a-methyl- 3 phenylpyrrolo[2,1-b]oxazol-5 (7a)-one, eterocyclic Building Blocks [294177 35 8] C 11 13 F 2 Br FW 273.14 473405 (1S,4S)-( )-2-(4 Fluorophenyl)- 2,5 diazabicyclo[2.2.1]heptane hydrobromide [308103 49 3] C 11 13 F 2 Br FW 273.14 Br F Br [116258 17 4] C 12 16 2 2Br FW 350.09 473030 Br Br (1S,4S)-( )-2-(4 Methylphenyl)- 2,5 diazabicyclo[2.2.1]heptane maleate salt, 95% [312624 04 7] C 12 16 2 C 4 4 4 FW 304.34 C 3 [302911 95 1] C 13 13 2 FW 215.25 458562 C 3 (3S-cis)-(+)-2,3 Dihydro-7a-methyl- 3 phenylpyrrolo[2,1-b]oxazol-5 (7a)-one, [143140 06 1] C 13 13 2 FW 215.25 473367 (4R,5S)-( )-1,5 Dimethyl-4 phenyl- 2 imidazolidinone, F 495271 (2R,4R)-(+)-4,5 Dihydro-4 iso- propyl-2-(p-tolyl)- 1,2λ 4,3 oxathiazole 2 oxide, 458570 Benzyl (S,S,S)-2 azabicyclo[3.3.0] octane-3 carboxylate hydrochloride, [92841 65 1] C 11 14 2 FW 190.24 3C [170900 87 5] C 12 17 2 S FW 239.33 S [87269 87 2] C 15 19 2 FW 281.78 382175 648337 570907 (4S,5R)-(+)-1,5 Dimethyl-4 phenyl- 2 imidazolidinone, [112791 04 5] C 11 14 2 FW 190.24 3C (2S,4S)-4,5 Dihydro-4 isopropyl-2- (p-tolyl)-1,2λ 4,3 oxathiazole 2 oxide, [145679 46 5] C 12 17 2 S FW 239.33 3C S ( )--(1(R)-Phenylethyl)-1 azabicyclo[2.2.2]octan-3(s)-amine dihydrochloride, [128311 06 8] C 15 22 2 2 FW 303.27 C 3 2 C 3 487244 380148 (S)-(+)-2,3 Dihydro-1-pyrrolo[2,1- c][1,4]benzodiazepine-5,11 (10,11a)-dione, [18877 34 4] C 12 12 2 2 FW 216.24 340650 648345 (S)-( )-9,10 Difluoro-2,3 dihydro- 3 methyl-7 oxo-7-pyrido-[1,2,3- de]-1,4 benzoxazine-6 carboxylic acid, [100986 89 8] C 13 9F 2 4 FW 281.21 F F C 3 (+)--(1(S)-Phenylethyl)-1 azabicyclo[2.2.2]octan-3(r)-amine dihydrochloride, [120570 09 4] C 15 22 2 2 FW 303.27 510343 Aloperine, 96% 2 (S)-( )-1 Z-2 xo-5 imidazolidinecarboxylic acid, [59760 01 9] C 12 12 2 5 FW 264.23 Cbz 570877 C 3 [56293 29 9] C 15 24 2 FW 232.36 546704 392308 18 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(2S-cis)-(+)-2,3 Dihydro-3 hydroxy- 2-(4 methoxyphenyl)-1,5 benzothiazepin-4(5)-one, [42399 49 5] C 16 15 3 S FW 301.36 475548 (+)-Usnic acid, [7562 61 0] C 18 16 7 FW 344.32 329967 3C 3C S 3C C 3 C 3 (3S-cis)-(+)-Tetrahydro-3,7adiphenylpyrrolo[2,1-b]oxazol-5 (6)-one, [161970 71 4] C 18 17 2 FW 279.33 458538 (2S)-( )-2,2 -xybis(octahydro- 7,8,8 trimethyl-4,7 methanobenzofuran), [108031 80 7] C 24 38 3 FW 374.56 3C C 3 3C C 3 3C 3C Ergotamine D-tartrate, 97.0% (T, calc. based on dry substance) Ph 3C [379 79 3] C 33 35 5 5 0.5C 4 6 6 FW 656.70 45510 ½ eterocyclic Building Blocks 385298 Discovery CPR Custom Packaged Reagents The ew Standard in Reagent Management for Medicinal Chemistry and rganic Synthesis Flexible Efficient Convenient Internet-based reagent database and procurement Powerful new batch-search and reporting capabilities Determine price and availability from your desktop rder products from more than 100 vendors rder in any amount, from micromoles to grams 24 48 hour turnaround time for most compounds Discovery CPR When projects demand custom arrays of reagents, Discovery CPR can meet the challenge. Reduces waste by eliminating on-site stocking and inventory management o minimum order required Specify vial type, labeling/bar-coding and packaging For more information visit DiscoveryCPR.com sigma-aldrich.com Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 19

Discover Unprotected Amino Aldehydes from Professor Yudin Professor Andrei Yudin and co-workers have recently described the preparation of bench-stable, unprotected α-amino aldehydes. 1 These kinetically amphoteric molecules exist as dimers, and due to the strain of the aziridine ring, resist inter- and intramolecular iminium ion formation. Furthermore, the two functionalities remain orthogonal to each other throughout their transformations, allowing for the reaction of the aldehyde without the requirement of an additional protecting group. Unprotected Vinyl Aziridines via lefination R 2 C PPh 3 Br Ph R t-buk, TF, 3 h 70-95% R R R Whereas the reductive amination of protected amino aldehydes has significant limitations due to epimerization or overalkylation, these Yudin amino aldehyde dimers do not suffer from either limitation, due to a negligible concentration of free aldehyde during the reaction. This allows the researcher facile access to a method for the creation of complex polycyclic skeletons 2 or peptidomimetic conjugates 3 with a high degree of stereocontrol. ucleophilic additions, 4 Wittig and related olefination reactions can be carried out with high selectivities and yields. Sigma-Aldrich is pleased to offer these useful Yudin amino aldehydes for your research. Cascade Polycyclizations R Unprotected Vicinal 1,2-Amino Alcohols via Allylation with Indium Reagents R 695556 In 0, Br TF/ 2, rt, 1 h R 81-96% > diastereoselectivity S 695521 Ph Bn Bn CF 3 C 2 0 C, 3 h Ph TBDMS 695513 707686 Synthesis of Peptidomimetic Conjugates Without Protecting Groups Ph 2 R 1 R 2 ab 3 C, Zn 2 TF/Me, rt Ph R 1 R 2 75-86% 695548 (1) ili, R.; Yudin, A. K. J. Am. Chem. Soc. 2006, 128, 14772. (2) Yudin, A. K.; ili, R. Chem. Eur. J. 2007, 13, 6538. (3) Li, X.; Yudin, A. K. J. Am. Chem. Soc. 2007, 129, 14152. (4) ili, R.; Yudin, A. K. Angew. Chem., Int. Ed. 2008, 47, 4188. sigma-aldrich.com

rganic Building Blocks Acid alides (S)-( )-2 Acetoxypropionyl chloride, [36394 75 9] C 5 7 3 FW 150.56 447056 (R)-( )--Formylmandeloyl chloride, [29169 64 0] C 9 7 3 FW 198.60 479284 3C C 3 (1S)-( )-Camphanic chloride, [39637 74 6] C 10 13 3 FW 216.66 3C 3C 3C (S)-(+)-α-Methoxy-α-trifluoromethylphenylacetyl chloride, [20445 33 4] C 10 8F 3 2 FW 252.62 369675 (1S)-(+)-Menthyl chloroformate [7635 54 3] C 11 19 2 FW 218.72 378712 3C (1R)-( )-Menthyl chloroformate [14602 86 9] C 11 19 2 FW 218.72 3C CF 3 3C C 3 C 3 ( )-Menthoxyacetyl chloride, [15356 62 4] C 12 21 2 FW 232.75 453714 3C ( )-1-(9 Fluorenyl)ethyl chloroformate solution [154479 90 0] C 16 13 2 FW 272.73 338710 (+)-1-(9 Fluorenyl)ethyl chloroformate solution [107474 79 3] C 16 13 2 FW 272.73 C 3 C 3 3C rganic Building Blocks 226173 245305 3C 335975 Alcohols (S)-(+)-2 Chloro-1 propanol, [19210 21 0] C 3 7 FW 94.54 296708 3C (R)-( )-3 Bromo-2 methyl-1 propanol, [93381 28 3] C 4 9Br FW 153.02 Br (S)-(+)-2 Butanol, [4221 99 2] C 4 10 FW 74.12 237698 3C (R)-(+)-3 Butyn-2 ol, [42969 65 3] C 4 6 FW 70.09 464821 (S)-( )-3 Butyn-2 ol, [2914 69 4] C 4 6 FW 70.09 464007 3C 3C (S)-1,4 Dibromo-2 butanol, 95.0% (GC, sum of enantiomers) C C 325066 (S)-(+)-3 Bromo-2 methyl-1 propanol, [98244 48 5] C 4 9Br FW 153.02 325058 (R)-( )-2 Butanol, [14898 79 4] C 4 10 FW 74.12 236691 Br 3C C 3 (R)-( )-1 Methoxy-2 propanol, 98.5% (GC, sum of enantiomers) [4984 22 9] C 4 10 2 FW 90.12 77913 3C (S)-(+)-1 Methoxy-2 propanol, 98.5% (sum of enantiomers) [26550 55 0] C 4 10 2 FW 90.12 88808 3C [64028 90 6] C 4 8 Br 2 FW 231.91 Br Br 77082 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 21

rganic Building Blocks (R)-( )-4 Penten-2 ol, 95% [64584 92 5] C 5 10 FW 86.13 558036 (S)-(+)-4 Penten-2 ol, 95% [55563 79 6] C 5 10 FW 86.13 558028 2C 2C (R)-5 Chloro-2 pentanol, 95% (GC, sum of enantiomers) [76188 95 9] C 5 11 FW 122.59 27618 (S)-(+)-2 Pentanol, [26184 62 3] C 5 12 FW 88.15 330515 3C C 3 (R)-( )-2,2 Dimethyl-1,3 dioxolane- 4 methanol, [14347 78 5] C 6 12 3 FW 132.16 241806 3C C 3 (R)-6 Chloro-2 hexanol, 98.0% (GC, sum of enantiomers) [154885 33 3] C 6 13 FW 136.62 78751 (S)-(+)-2 exanol, [52019 78 0] C 6 14 FW 102.17 655236 3C (S)-(+)-4 Methyl-2 pentanol, [14898 80 7] C 6 14 FW 102.17 3C C 3 (+)-endo-2 orborneol, 96% [61277 90 5] C 7 12 FW 112.17 543519 (1R,2R)-trans-2 Acetoxy-1 cyclopentanol, 99.0% (GC, sum of enantiomers) [105663 22 7] C 7 12 3 FW 144.17 00846 (S)-( )-1,1,1 Trifluoroheptan-2 ol, [130025 35 3] C 7 13F 3 FW 170.17 532525 C 3(C 2) 3C 2 (4R)-4-(2 ydroxyethyl)-2,2 dimethyl-1,3 dioxolane, 96% CF 3 (R)-( )-2 Pentanol, [31087 44 2] C 5 12 FW 88.15 330523 3C (S)-( )-2 Methyl-1 butanol, 558079 (R)-( )-4 Methyl-2 pentanol, [16404 54 9] C 6 14 FW 102.17 558052 3C 3C C 3 [70005 89 9] C 7 14 3 FW 146.18 331074 3C C 3 (4S)-(+)-4-(2 ydroxyethyl)-2,2 dimethyl-1,3 dioxolane, 96% [1565 80 6] C 5 12 FW 88.15 A83407 (S)-(+)-5 exen-2 ol, [17397 24 9] C 6 12 FW 100.16 558044 (R)-( )-5 exen-2 ol, [17397 29 4] C 6 12 FW 100.16 558060 2C 2C 3C C 3 C 3 (S)-(+)-1,2 Isopropylideneglycerol, [22323 82 6] C 6 12 3 FW 132.16 3C (R)-( )-2 exanol, [26549 24 6] C 6 14 FW 102.17 340308 3C (1S,4R)-cis-4 Acetoxy-2 cyclopenten-1 ol, [60410 16 4] C 7 10 3 FW 142.15 446041 (1R,4S)-cis-4 Acetoxy-2 cyclopenten-1 ol, 98.0% (GC, sum of enantiomers) [60176 77 4] C 7 10 3 FW 142.15 00848 3C C 3 [32233 43 5] C 7 14 3 FW 146.18 571326 3C C 3 (4S,5S)-2,2 Dimethyl-1,3 dioxolane-4,5 dimethanol, 97.0% (GC, sum of enantiomers) [50622 09 8] C 7 14 4 FW 162.18 59539 (R)-( )-2 eptanol, 95% [6033 24 5] C 7 16 FW 116.20 408697 3C C 3 (C2)3C2 237744 22 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(S)-(+)-2 eptanol, [6033 23 4] C 7 16 FW 116.20 340332 (C2)3C2 (R)-( )-2-[(RS)-1 Ethoxyethoxy]- 1 propanol, 95.0% (GC, sum of enantiomers) [64028 92 8] C 7 16 3 FW 148.20 17241 3C 3C (S)-4 Bromo-α-methylbenzyl alcohol, 95% [100760 04 1] C 8 9 Br FW 201.06 686301 Br (S)-(+)-2 Chloro-1 phenylethanol, 97.0% (GC, sum of enantiomers) [70111 05 6] C 8 9 FW 156.61 25905 C 3 (R)-1 Phenylethanol, [1517 69 7] C 8 10 FW 122.16 685828 (S)-1 Phenylethanol, [1445 91 6] C 8 10 FW 122.16 685836 (S)-( )-1 ctyn-3 ol, rganic Building Blocks (R)-( )-α-(trifluoromethyl)benzyl alcohol, [10531 50 7] C 8 7F 3 FW 176.14 CF3 (R)-( )-2 Chloro-1 phenylethanol, [56751 12 3] C 8 9 FW 156.61 [32556 71 1] C 8 14 FW 126.20 393967 (R)-(+)-1 ctyn-3 ol, (C2)3C2 C 411132 (S)-(+)-α-(Trifluoromethyl)benzyl alcohol, 363561 (R)-4 Chloro-α-methylbenzyl alcohol, 95% [32556 70 0] C 8 14 FW 126.20 399701 C 3(C 2) 3C 2 C [340 06 7] C 8 7F 3 FW 176.14 411140 (R)-(+)-2 Bromo-α-methylbenzyl alcohol, [76116 20 6] C 8 9Br FW 201.06 429791 (S)-( )-2 Bromo-α-methylbenzyl alcohol, [114446 55 8] C 8 9 Br FW 201.06 327247 Br (R)-4 Bromo-α-methylbenzyl alcohol, 95% [76155 78 7] C 8 9 Br FW 201.06 686336 Br Br CF3 C 3 C 3 [75968 40 0] C 8 9 FW 156.61 686298 (S)-4 Chloro-α-methylbenzyl alcohol, 95% [99528 42 4] C 8 9 FW 156.61 686271 (S)-4 Fluoro-α-methylbenzyl alcohol, [101219 73 2] C 8 9 F FW 140.15 685852 F (R)-4 Fluoro-α-methylbenzyl alcohol, [101219 68 5] C 8 9F FW 140.15 685844 F C 3 C 3 (R)-(+)-1,1,1 Trifluoro-2 octanol, [121170 45 4] C 8 15F 3 FW 184.20 537187 (C2)4C2 (S)-( )-1,1,1 Trifluoro-2 octanol, [129443 08 9] C 8 15F 3 FW 184.20 532533 (C2)4C2 (S)-1 cten-3 ol, 95% (PLC, sum of enantiomers) [24587 53 9] C 8 16 FW 128.21 40577 (C2)3C2 (R)-(+)-1 Fluoro-2 octanol, [110270 42 3] C 8 17F FW 148.22 477362 CF3 CF3 C 2 (C2)4C2 F Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 23

(R)-( )-2 ctanol, (R)-( )-1 Indanol, (R)-(+)-1 Phenyl-1 propanol, [5978 70 1] C 8 18 FW 130.23 C 3(C 2) 4C 2 C 3 [697 64 3] C 9 10 FW 134.18 [1565 74 8] C 9 12 FW 136.19 rganic Building Blocks 147990 (S)-(+)-2 ctanol, [6169 06 8] C 8 18 FW 130.23 147982 (S)-(+)-3 ctanol, [22658 92 0] C 8 18 FW 130.23 666718 3C (C2)4C2 C 3 (R)-1 Phenyl-2 propyn-1 ol, 99.0% (GC, sum of enantiomers) [61317 73 5] C 9 8 FW 132.16 78976 (S)-1 Phenyl-2 propyn-1 ol, 99.0% (GC, sum of enantiomers) C 328413 (S)-1 Phenyl-2 propen-1 ol, 97.0% (GC, sum of enantiomers) [39623 35 3] C 9 10 FW 134.18 78974 (R)-1 Phenyl-2 propen-1 ol, 95% (GC, sum of enantiomers) [104713 12 4] C 9 10 FW 134.18 78972 (S)-( )-3 Chloro-1 phenyl-1 propanol, [100306 34 1] C 9 11 FW 170.64 324612 C 2 C 2 256331 (S)-( )-1 Phenyl-1 propanol, [613 87 6] C 9 12 FW 136.19 256323 (R)-( )-1 Phenyl-2 propanol, 97.0% (GC, sum of enantiomers) [1572 95 8] C 9 12 FW 136.19 78926 (R)-(+)-2 Phenyl-1 propanol, [19141 40 3] C 9 12 FW 136.19 461407 (S)-( )-2 Phenyl-1 propanol, C 3 C 3 C 3 [64599 56 0] C 9 8 FW 132.16 C (R)-(+)-3 Chloro-1 phenyl-1 propanol, [37778 99 7] C 9 12 FW 136.19 C 3 78978 (S)-( )-1 Chloro-3-(4 fluorophenoxy)-2 propanol, [100306 33 0] C 9 11 FW 170.64 338419 461415 (S)-(+)-1 Phenyl-2 propanol, 97.0% (GC, sum of enantiomers) [352530 45 1] C 9 10F 2 FW 204.63 537128 (R)-(+)-1 Chloro-3-(4 fluorophenoxy)-2 propanol, [307532 04 3] C 9 10 F 2 FW 204.63 537101 (S)-(+)-1 Indanol, F F (S)-(+)-1-(4 Fluorophenoxy)-2 propanol, [206125 75 9] C 9 11F 2 FW 170.18 537098 F (R)-( )-1-(4 Fluorophenoxy)-2 propanol, [307532 03 2] C 9 11 F 2 FW 170.18 F C 3 [1517 68 6] C 9 12 FW 136.19 78927 (S)-(+)-2 Methoxy-2 phenylethanol, [66051 01 2] C 9 12 2 FW 152.19 302147 (R)-( )-2 Methoxy-2 phenylethanol, C 3 [25501 32 0] C 9 10 FW 134.18 537071 [17628 72 7] C 9 12 2 FW 152.19 323128 302775 24 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

D-α,β-Cyclohexylideneglycerol, 98.0% (GC, sum of enantiomers) [95335 91 4] C 9 16 3 FW 172.22 29400 (S)-(+)-2 onanol, [70419 06 6] C 9 20 FW 144.25 557978 3C (R)-( )-2 onanol, [70419 07 7] C 9 20 FW 144.25 557951 3C (R)-1-[3,5 Bis(trifluoromethyl)phenyl]ethanol, 98.0% (GC) [127852 28 2] C 10 8F 6 FW 258.16 49554 F 3C CF3 (S)-(+)-1,2,3,4 Tetrahydro-1 naphthol, [53732 47 1] C 10 12 FW 148.20 256293 (S)-(+)-4 Phenyl-2 butanol, [22148 86 3] C 10 14 FW 150.22 558095 (R)-( )-4 Phenyl-2 butanol, [39516 03 5] C 10 14 FW 150.22 558109 (R)-( )-1 Benzyloxy-2 propanol, [89401 28 5] C 10 14 2 FW 166.22 650846 3C (S)-(+)-1 Benzyloxy-2 propanol, [85483 97 2] C 10 14 2 FW 166.22 650838 3C (R)-Glycerol 1-(p-toluenesulfonate), 95% (TLC) [41274 09 3] C 10 14 5 S FW 246.28 G2410 3C S C 3 C 3 ( )-trans-pinocarveol, 96.0% (GC, sum of enantiomers) [547 61 5] C 10 16 FW 152.23 80613 (S)-cis-Verbenol, 95% [18881 04 4] C 10 16 FW 152.23 247065 (+)-Borneol, [464 43 7] C 10 18 FW 154.25 420247 ( )-Borneol, [464 45 9] C 10 18 FW 154.25 139114 3C 3C 3C (1S,2S,5S)-( )-Myrtanol, [53369 17 8] C 10 18 FW 154.25 3C C 3 C 2 C 3 3C 3C 3C rganic Building Blocks (R)-( )-1,2,3,4 Tetrahydro-1 naphthol, [23357 45 1] C 10 12 FW 148.20 256285 (R)-(+)-1 Phenyl-1 butanol, [22144 60 1] C 10 14 FW 150.22 317314 (S)-( )-1 Phenyl-1 butanol, C 3 (S)-( )-Perillyl alcohol, 96% [18457 55 1] C 10 16 FW 152.23 218391 (1R)-( )-Myrtenol, 95% [19894 97 4] C 10 16 FW 152.23 188417 2C 3C ( )-Carveol, mixture of isomers, 274178 (1R)-endo-(+)-Fenchyl alcohol, 96% [2217 02 9] C 10 18 FW 154.25 196444 (+)-Dihydrocarveol, 95.0% (GC, sum of enantiomers) [22567 21 1] C 10 18 FW 154.25 37277 2C 3C C 3 C 3 C 3 [22135 49 5] C 10 14 FW 150.22 317322 [99 48 9] C 10 16 FW 152.23 192384 2C C 3 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 25

rganic Building Blocks ( )-Dihydrocarveol, 95.0% (GC, sum of enantiomers) [20549 47 7] C 10 18 FW 154.25 37278 (+)-Isopulegol, [104870 56 6] C 10 18 FW 154.25 439053 ( )-Isopulegol, 2C 2C C 3 C 3 (1S,2S,3S,5R)-(+)-Isopinocampheol, [27779 29 9] C 10 18 FW 154.25 250856 3C 3C (1R,2R,3R,5S)-( )-Isopinocampheol, [25465 65 0] C 10 18 FW 154.25 221902 3C 3C C 3 (R)-( )-2 Decanol, [33758 15 5] C 10 22 FW 158.28 557986 (C2)6C2 (S)-3 Butene-1,2 diol-1-(p-toluenesulfonate), 99.0% (PLC) [133095 74 6] C 11 14 4S FW 242.29 19163 3C S (R)-3 Butene-1,2 diol-1-(p-toluenesulfonate), 99.0% (PLC) C 2 [89 79 2] C 10 18 FW 154.25 439061 2C ( )-Linalool, 95.0% (GC, sum of enantiomers) [126 91 0] C 10 18 FW 154.25 62139 α-terpineol, 90% [10482 56 1] C 10 18 FW 154.25 432628 C 3 3C C2 3C 3C 3C C 3 (1S,2S,4R)-(+)-Limonene-1,2 diol, 97.0% (GC) [38630 75 0] C 10 18 2 FW 170.25 669768 (R)-(+)-β-Citronellol, [1117 61 9] C 10 20 FW 156.27 303461 3C (S)-( )-β-citronellol, [7540 51 4] C 10 20 FW 156.27 3C 2C C 3 C 3 [138249 07 7] C 11 14 4S FW 242.29 19162 3C (1R)-( )-opol, [35836 73 8] C 11 18 FW 166.26 340367 S 3C 2 Methylisoborneol solution, (GC) [2371 42 8] C 11 20 FW 168.28 3C C 3 3C C 2 ( )-Terpinen-4 ol, 95.0% (GC, sum of enantiomers) [20126 76 5] C 10 18 FW 154.25 11584 Isoborneol, 95% [124 76 5] C 10 18 FW 154.25 I13901 3C 3C C 3 303488 (1R,2S,5R)-( )-Menthol, [2216 51 5] C 10 20 FW 156.27 M2780 3C (1S,2R,5S)-(+)-Menthol, [15356 60 2] C 10 20 FW 156.27 224464 3C (1S,2S,5R)-(+)-eomenthol, [2216 52 6] C 10 20 FW 156.27 3C C 3 C 3 C 3 C 3 C 3 C 3 M3933 (R)-(+)-α Methyl-1 naphthalenemethanol, [42177 25 3] C 12 12 FW 172.22 372315 3C (S)-( )-α Methyl-1 naphthalenemethanol, [15914 84 8] C 12 12 FW 172.22 372323 3C 235180 26 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(R)-(+)-1-(2 aphthyl)ethanol, [52193 85 8] C 12 12 FW 172.22 346217 (S)-( )-α Methyl-2 naphthalenemethanol, [27544 18 9] C 12 12 FW 172.22 323144 (1R,2S)-trans-2 Phenyl-1 cyclohexanol, C 3 (1S,2R)-(+)-trans-2-(1 Methyl- 1 phenylethyl)cyclohexanol, [109527 45 9] C 15 22 FW 218.33 453404 C 3 (1R,2S)-( )-trans-2-(1 Methyl- 1 phenylethyl)cyclohexanol, [109527 43 7] C 15 22 FW 218.33 453390 ( )-Guaiol, C 3 (S)-( )-1 Phenyl-1 decanol, 95% [112419 76 8] C 16 26 FW 234.38 331619 (C2)7C2 (S)-( )-2,3 Dibenzyloxy-1 propanol, 96% [20196 71 8] C 17 20 3 FW 272.34 526150 (S)-2 Benzyloxy-1,3 propanediol 1- (p-toluenesulfonate), 99.0% (PLC, sum of enantiomers) Ph Ph rganic Building Blocks [98919 68 7] C 12 16 FW 176.25 367249 (1S,2R)-(+)-trans-2 Phenyl-1 cyclohexanol, [34281 92 0] C 12 16 FW 176.25 367257 (S)-( )-1,1,1,2,2 Pentafluorododecan-3 ol, [307531 78 8] C 12 21F 5 FW 276.29 532517 (C2)7C2 (S)-( )-1-(9 Fluorenyl)ethanol, 99.0% (PLC) [151775 20 1] C 15 14 FW 210.27 3C CF2CF3 [489 86 1] C 15 26 FW 222.37 448575 3C C 3 3C C 3 (R)-( )-1-(9 Anthryl)-2,2,2 trifluoroethanol, [53531 34 3] C 16 11 F 3 FW 276.25 211354 CF 3 (S)-(+)-1-(9 Anthryl)-2,2,2 trifluoroethanol, [60646 30 2] C 16 11 F 3 FW 276.25 211346 ( )-8 Phenylmenthol, [65253 04 5] C 16 24 FW 232.36 CF 3 3C C 3 [109371 30 4] C 17 20 5 S FW 336.40 13746 3C S (R)-( )-1 Benzyloxy-3-(p-tosyloxy)- 2 propanol, 95% 3C [23214 66 6] C 17 20 5 S FW 336.40 364886 S (R)-(+)-1-(2,4,6 Triisopropylphenyl) ethanol, 96.0% (PLC) [181531 14 6] C 17 28 FW 248.40 672599 i-pr i-pr i-pr 00925 329487 (S)-(+)-1 Phenyl-1,2 ethanediol 2 tosylate, [40435 14 1] C 15 16 4 S FW 292.35 317853 3C S (+)-8 Phenylmenthol, 98.0% (PLC, sum of enantiomers) [57707 91 2] C 16 24 FW 232.36 3C C 3 78803 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 27

rganic Building Blocks (S)-( )-1-(2,4,6 Triisopropylphenyl) ethanol, 98.5% (PLC) [102225 88 7] C 17 28 FW 248.40 672483 i-pr i-pr i-pr (1S,2R,4S)-(+)-4-(1 Methylethyl)-2- (1 methyl-1 phenylethyl)cyclohexanol, (C 3 ) 2 CC 6 9 [C(C 3 ) 2C 6 5] 453420 3C 3C (1R,2S,4R)-( )-4-(1 Methylethyl)-2- (1 methyl-1 phenylethyl)cyclohexanol, [167752 95 6] C 18 28 FW 260.41 453412 3C 3C (4bS)-trans-8,8 Trimethyl- 4b,5,6,7,8,8a,9,10 octahydro-1 isopropylphenanthren-2 ol, [511 15 9] C 20 30 FW 286.45 3C 3C (4aR)-trans-5-(1,5,5,8aS-Tetra- methyl-2 methylenedecahydro- 1 naphthalenyl)-(3r)-methyl- 1 penten-3 ol, [596 85 0] C 20 34 FW 290.48 532665 3C 3C C 3 C2 C2 2,3 Dilauroyl-sn-glycerol, 99.0% (TLC) [61475 84 1] C 27 52 5 FW 456.70 3C(2C)10 532657 38481 (C2)10 Aldehydes (R)-(+)-2,2 Dimethyl-1,3 dioxolane- 4 carboxaldehyde [15186 48 8] C 6 10 3 FW 130.14 454486 (R)-1,4 Dioxaspiro[4.5]decane- 2 carboxaldehyde [78008 36 3] C 9 14 3 FW 170.21 543039 3C ( )-Myrtenal, 97.0% (GC, sum of enantiomers) [18486 69 6] C 10 14 FW 150.22 70125 (+)-Perillaaldehyde, 98.0% (GC, sum of enantiomers) [5503 12 8] C 10 14 FW 150.22 2C 3C (S)-( )-Perillaldehyde, 92% [18031 40 8] C 10 14 FW 150.22 218294 (R)-(+)-Citronellal, 90% [2385 77 5] C 10 18 FW 154.25 343641 3C (S)-( )-Citronellal, 96% 2C C 3 (1R)-( )-Myrtenal, [18486 69 6] C 10 14 FW 150.22 3C 77301 [5949 05 3] C 10 18 FW 154.25 373753 3C C 3 C 3 218243 28 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

Amides (R)-(+)-Lactamide, [598 81 2] C 3 7 2 FW 89.09 436801 (S)-( )-Lactamide, [89673 71 2] C 3 7 2 FW 89.09 436828 3C 3C (S)-(+)-2 Aminobutanamide hydrochloride, 2 2 (+)-,,, -Tetramethyl-L-tartaric acid diamide, [26549 65 5] C 8 16 2 4 FW 204.22 376418 C 3 3C C 3 2,2,2 Trifluoro--[(S)-α-methylbenzyl]acetamide, [39995 51 2] C 10 10F 3 FW 217.19 399779 CF3 (+)-, -Dibenzyl-L-tartaric diamide, [88393 56 0] C 18 20 2 4 FW 328.36 276057 ( )-, -Dibenzyl-D-tartaric diamide, [108321 43 3] C 18 20 2 4 FW 328.36 276065 rganic Building Blocks [7682 20 4] C 4 11 2 FW 138.60 679399 3C 2 2 (R)-( )-2 Aminobutanamide hydrochloride, [103765 03 3] C 4 11 2 FW 138.60 679380 3C 2 2 (+)-, -Diallyltartramide, [58477 85 3] C 10 16 2 4 FW 228.25 156868 2C (R)-( )-3,5 Dinitro--(1 phenylethyl)benzamide, [69632 32 2] C 15 13 3 5 FW 315.28 2 C 2 (R)-( )--[1-(1 aphthyl)ethyl]- 3,5 dinitrobenzamide, [85922 30 1] C 19 15 3 5 FW 365.34 461601 2 2 (S)-(+)--[1-(1 aphthyl)ethyl]- 3,5 dinitrobenzamide, (R)-( )-2,2 Dimethylcyclopropane- 1 carboxamide, [106462 18 4] C 6 11 FW 113.16 679410 3C (S)-(+)-2,2 Dimethylcyclopropanecarboxamide, [75885 58 4] C 6 11 FW 113.16 434639 3C,,, -Tetramethyl-D-tartaramide, 2 2 296902 2 (S)-(+)-3,5 Dinitro--(1 phenylethyl)benzamide, [69632 31 1] C 15 13 3 5 FW 315.28 296910 2 2 α-xo--[(r)-1 phenylethyl] phenylacetamide, [10549 15 2] C 16 15 2 FW 253.30 422290 C 3 C 3 [85922 31 2] C 19 15 3 5 FW 365.34 461628 2 2 ( )-, -Dibenzoyl-L-tartaric acid mono(dimethylamide), 99.0% (T) [78761 37 2] C 20 19 7 FW 385.37 33624 3C [63126 52 3] C 8 16 2 4 FW 204.22 C 3 3C C 3 376396 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 29

Amines rganic Building Blocks (S)-(+)-sec-Butylamine, [513 49 5] C 4 11 FW 73.14 296651 (R)-( )-sec-butylamine, [13250 12 9] C 4 11 FW 73.14 296643 3C 3C (S)-( )-sec-butylamine hydrochloride, 98.0% (AT) C 4 11 FW 109.60 94212 3C 2 2 C 3 2 C 3 (S)-( )-2 Methylbutylamine, 95% [34985 37 0] C 5 13 FW 87.16 241407 3C (S)-(+)-2 Amino-3 methylbutane, 98.0% (GC) [22526 46 1] C 5 13 FW 87.16 91936 2 2 3C (R)-( )-2 Amino-3 methylbutane, 97.0% (GC) [34701 33 2] C 5 13 FW 87.16 18241 2 3C (S)-(+)-3,3 Dimethyl-2 butylamine, [22526 47 2] C 6 15 FW 101.19 668516 3C 3C 3C (R)-( )-3,3 Dimethyl-2 butylamine, 2 (S)-2 Aminohexane, 97.0% (GC) [70492 67 0] C 6 15 FW 101.19 77914 3C (R)-2 Aminohexane, 97.0% (GC) [70095 40 8] C 6 15 FW 101.19 30192 3C (R)-( )-2 Aminoheptane, [6240 90 0] C 7 17 FW 115.22 462624 3C (S)-(+)-2 Aminoheptane, [44745 29 1] C 7 17 FW 115.22 462632 3C 2 2 2 2 [27298 97 1] C 8 10 Br FW 200.08 18072 Br 2 (S)-( )-1-(4 Bromophenyl)ethylamine, 98.0% (GC, sum of enantiomers) (R)-(+)-1-(4 Bromophenyl)ethylamine, 96.0% (GC, sum of enantiomers) [45791 36 4] C 8 10 Br FW 200.08 18069 Br 2 C 3 C 3 C 3 C 3 (R)-4 Chloro-α-methylbenzylamine, 95.0% (GC) [27298 99 3] C 8 10 FW 155.62 18196 2 C 3 (S)-4 Chloro-α-methylbenzylamine, 95.0% (GC) [4187 56 8] C 8 10 FW 155.62 19506 (R)-α-Methyl-4 nitrobenzylamine hydrochloride, [57233 86 0] C 8 10 2 2 FW 202.64 339814 2 2 (S)-α-Methyl-4 nitrobenzylamine hydrochloride, [132873 57 5] C 8 10 2 2 FW 202.64 339822 2 2 C 3 C 3 2 (R)-(+)-α-Methylbenzylamine, [3886 69 9] C 8 11 FW 121.18 115541 2 (S)-( )-α-methylbenzylamine, [2627 86 3] C 8 11 FW 121.18 115568 (R)-( )-1 Cyclohexylethylamine, [5913 13 3] C 8 17 FW 127.23 336505 (S)-(+)-1 Cyclohexylethylamine, [17430 98 7] C 8 17 FW 127.23 2 2 C 3 2 C 3 [66228 31 7] C 6 15 FW 101.19 3C 3C 3C 2 336513 668427 30 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(R)-2 Aminooctane, 98.0% (GC) [34566 05 7] C 8 19 FW 129.24 93786 3C (S)-2 Aminooctane, 97.0% (GC) [34566 04 6] C 8 19 FW 129.24 05023 3C (S)-(+)-1 Aminoindan, [61341 86 4] C 9 11 FW 133.19 445355 (R)-( )-1 Aminoindane, [10277 74 4] C 9 11 FW 133.19 445347 2 2 2 2 (R)-(+)-,α-Dimethylbenzylamine, [5933 40 4] C 9 13 FW 135.21 394009 C 3 C 3 (S)-( )-,α-dimethylbenzylamine, [19131 99 8] C 9 13 FW 135.21 401358 C 3 (R)-(+)-α,4 Dimethylbenzylamine, [4187 38 6] C 9 13 FW 135.21 405248 3C (R)-(+)-β-Methylphenethylamine, 2 C 3 (R)-( )-1,2,3,4 Tetrahydro-1 naphthylamine, [23357 46 2] C 10 13 FW 147.22 668818 (S)-( )-,-Dimethyl-1 phenylethylamine, [17279 31 1] C 10 15 FW 149.23 242063 (R)-(+)-,-Dimethyl-1 phenylethylamine, [19342 01 9] C 10 15 FW 149.23 242071 C 3 (S)-(+)-α-(Methoxymethyl)phenethylamine hydrochloride, 2 C 3 C 3 rganic Building Blocks (S)-( )-α,4 Dimethylbenzylamine, [27298 98 2] C 9 13 FW 135.21 405256 3C 2 (S)-β-Methylphenethylamine, [17596 79 1] C 9 13 FW 135.21 461393 C 3 C 3 2 [28163 64 6] C 9 13 FW 135.21 461385 2 (S)-( )-4 Methoxy-α-methylbenzylamine, 98.0% (GC, sum of enantiomers) [41851 59 6] C 9 13 FW 151.21 95889 3C 2 [64715 81 7] C 10 15 FW 201.69 459275 (R)-(+)-Bornylamine, [32511 34 5] C 10 19 FW 153.26 359939 2 3C 3C (1R,2R,3R,5S)-( )-Isopinocampheylamine, 95% 2 (S)-( )-α-ethylbenzylamine, 95.0% (GC) [3789 59 1] C 9 13 FW 135.21 51432 (R)-(+)-α-Ethylbenzylamine, 99.0% (GC) [3082 64 2] C 9 13 FW 135.21 2 C 3 2 C 3 (R)-(+)-4 Methoxy-α-methylbenzylamine, 95.0% (GC) [22038 86 4] C 9 13 FW 151.21 18159 3C (S)-(+)-1,2,3,4 Tetrahydro-1 naphthylamine, [23357 52 0] C 10 13 FW 147.22 2 C 3 2 [69460 11 3] C 10 19 FW 153.26 391654 3C 3C C 3 2 (1S,2S,3S,5R)-(+)-Isopinocampheylamine, 95% [13293 47 5] C 10 19 FW 153.26 391662 3C 3C 2 50282 668796 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 31

rganic Building Blocks ( )-cis-myrtanylamine, [38235 68 6] C 10 19 FW 153.26 180807 (R)-( )-Isobornylamine hydrochloride, 97.0% (AT) [24629 78 5] C 10 19 FW 189.73 58335 3C C 3 2 3C 2 (R)-(+)-1-(1 aphthyl)ethylamine hydrochloride, [82572 04 1] C 12 14 FW 207.70 656755 3C 2 (S)-( )-1-(1 aphthyl)ethylamine hydrochloride, [51600 24 9] C 12 14 FW 207.70 656747 3C 2 (S)-( )-,-Dimethyl-1-(1 naphthyl)ethylamine, [121045 73 6] C 14 17 FW 199.29 461504 3C (R)-(+)-,-Dimethyl-1-(1 naphthyl)ethylamine, 96% [119392 95 9] C 14 17 FW 199.29 3C C 3 (R)-(+)--allyl-α-methylbenzylamine, [126275 19 2] C 11 15 FW 161.24 559032 C 2 (1S,2S)-trans-2 Benzyloxycyclopentylamine, [181657 57 8] C 12 17 FW 191.27 671649 2 461490 (R)-1,1 Diphenyl-1 fluoro-2 aminopropane, C 15 16 F FW 229.29 F 2 (R)-(+)-1-(1 aphthyl)ethylamine, [3886 70 2] C 12 13 FW 171.24 237442 3C (S)-( )-1-(1 aphthyl)ethylamine, [10420 89 0] C 12 13 FW 171.24 237450 2 3C 2 (R)-(+)-1-(2 aphthyl)ethylamine, 99.0% (GC, sum of enantiomers) [3906 16 9] C 12 13 FW 171.24 70940 2 (S)-( )-1-(2 aphthyl)ethylamine, 99.0% (GC, sum of enantiomers) C 3 (R)-(+)--Methyl-1-(1 naphthyl) ethylamine, [15297 33 3] C 13 15 FW 185.26 461474 3C (S)-( )--Methyl-1-(1 naphthyl) ethylamine, [20218 55 7] C 13 15 FW 185.26 461482 3C (4S,5S)-(+)-2,2 Dimethyl-5 methylamino-4 phenyl-1,3 dioxane, 98.0% (GC, sum of enantiomers) [124686 47 1] C 13 19 2 FW 221.30 3C C 3 C 3 549525 (S)-1,1 Diphenyl-1 fluoro-2 aminopropane, C 15 16 F FW 229.29 549533 (R)-(+)-1,1 Diphenyl-2 aminopropane, C 15 17 FW 211.30 549495 (S)-( )-1,1 Diphenyl-2 aminopropane, [67659 37 4] C 15 17 FW 211.30 F 2 C 3 2 C 3 2 [3082 62 0] C 12 13 FW 171.24 2 C 3 40767 549487 70942 32 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(S)-( )--Benzyl-α-methylbenzylamine, (R)-(+)-2 Amino-1 fluoro-3 methyl- 1,1 diphenylbutane, (R)-(+)-2 Amino-4 methyl- 1,1 diphenylpentane, [17480 69 2] C 15 17 FW 211.30 427470 (R)-(+)--Benzyl-α-methylbenzylamine, [38235 77 7] C 15 17 FW 211.30 431737 C 17 20F FW 257.35 551090 3C (S)-( )-2 Amino-3 methyl- 1,1 diphenylbutane, [233772 37 7] C 17 21 FW 239.36 3C C 3 2 2 F [352535 73 0] C 18 23 FW 253.38 554618 (S)-( )-2 Amino-4 methyl- 1,1 diphenylpentane, [233772 40 2] C 18 23 FW 253.38 2 3C 2 3C rganic Building Blocks (+)-Bis[(R)-1 phenylethyl]amine, [23294 41 9] C 16 19 FW 225.33 452823 C 3 ( )-Bis[(S)-1 phenylethyl]amine, 551147 (R)-(+)-2 Amino-3 methyl- 1,1 diphenylbutane, [400870 29 3] C 17 21 FW 239.36 551155 3C 2 554626 (R)-( )--Benzyl-1-(1 naphthyl) ethylamine hydrochloride, [163831 65 0] C 19 19 FW 297.82 445959 3C [56210 72 1] C 16 19 FW 225.33 (S)-( )-2 Amino-1 fluoro-4 methyl- 1,1 diphenylpentane, (S)--Benzyl-1-(1 naphthyl)ethylamine hydrochloride, 96.0% (AT) 433810 (+)-Bis[(R)-1 phenylethyl]amine hydrochloride, [274674 22 5] C 18 22F FW 271.37 C 3 2 3C F [163831 66 1] C 19 19 FW 297.82 3C [82398 30 9] C 16 19 FW 261.79 461520 ( )-Bis[(S)-1 phenylethyl]amine hydrochloride, 554642 (R)-(+)-2 Amino-1 fluoro-4 methyl- 1,1 diphenylpentane, [352535 74 1] C 18 22 F FW 271.37 3C C 3 2 F 13597 (S)-( )-1,2,2 Triphenylethylamine, [352535 04 7] C 20 19 FW 273.37 2 [40648 92 8] C 16 19 FW 261.79 445940 (S)-( )-2 Amino-1 fluoro-3 methyl- 1,1 diphenylbutane, C 17 20 F FW 257.35 3C 2 F 554634 (S)-(+)-2 Amino-3,3 dimethyl- 1,1 diphenylbutane, [352535 91 2] C 18 23 FW 253.38 557919 t-bu 2 553220 (R)-(+)-1,2,2 Triphenylethylamine, C 20 19 FW 273.37 553247 2 551074 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 33

(R)-(+)-1 Benzyl-2,2 diphenylethylamine, (R)-, -Dimethyl-1,1 -binaphthyldiamine, 99.0% Bis[(R)-( )-(1 naphthyl)ethyl]amine hydrochloride, rganic Building Blocks [94964 58 6] C 21 21 FW 287.40 554510 2 (S)-( )-1 Benzyl-2,2 diphenylethylamine, [233772 38 8] C 21 21 FW 287.40 2 [93713 30 5] C 22 20 2 FW 312.41 672408 (S)-, -Dimethyl-1,1 -binaphthyldiamine, 99.0% [666175 40 2] C 22 20 2 FW 312.41 [312619 39 9] C 24 23 FW 361.91 461652 C 3 Bis[(S)-(+)-(1 naphthyl)ethyl]amine hydrochloride, [171867 34 8] C 24 23 FW 361.91 461660 C 3 554529 672297 Amino Alcohols (R)-( )-1 Amino-2 propanol, [2799 16 8] C 3 9 FW 75.11 238856 3C 2 (R)-( )-2 Amino-1 butanol, [5856 63 3] C 4 11 FW 89.14 307084 3C 2 (R)-( )-2 Amino-3 methyl-1 butanol, [4276 09 9] C 5 13 FW 103.16 3C 2 (S)-(+)-1 Amino-2 propanol, (S)-(+)-2 Amino-1 butanol, 284483 [2799 17 9] C 3 9 FW 75.11 238864 3C (R)-( )-2 Amino-1 propanol, [35320 23 1] C 3 9 FW 75.11 297682 2 3C 2 [5856 62 2] C 4 11 FW 89.14 132527 3C 2 (1R,2R)-trans-2 Aminocyclopentanol hydrochloride, [68327 11 7] C 5 11 FW 137.61 2 (S)-(+)-2 Amino-3 methyl-1 butanol, 96% [2026 48 4] C 5 13 FW 103.16 186708 3C C 3 (S)-(+)-1 Dimethylamino-2 propanol, 2 (S)-(+)-2 Amino-1 propanol, [2749 11 3] C 3 9 FW 75.11 A76206 3C 2 (S)-3 Amino-1,2 propanediol, [61278 21 5] C 3 9 2 FW 91.11 473960 2 (R)-3 Amino-1,2 propanediol, 98.0% (T) [66211 46 9] C 3 9 2 FW 91.11 2 671878 (1S,2S)-trans-2 Aminocyclopentanol hydrochloride, 98.0% (TLC) [68327 04 8] C 5 11 FW 137.61 06782 2 (1R,2S)-cis-2 Aminocyclopentanol hydrochloride, 98.0% (TLC) [137254 03 6] C 5 11 FW 137.61 06756 2 [53636 17 2] C 5 13 FW 103.16 462039 3C (S)-(+)-2 Amino-1 pentanol, [22724 81 8] C 5 13 FW 103.16 534587 3C (R)-( )-2 Amino-1 pentanol, [80696 30 6] C 5 13 FW 103.16 534579 3C 2 2 09267 34 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(1S,2S)-(+)-2 Aminocyclohexanol hydrochloride, 98.5 101.5% (AT) (S)-(+)-orepinephrine L-bitartrate, (1S,2S)-(+)-trans-1 Amino-2 indanol, [13374 30 6] C 6 13 FW 151.63 671959 2 (1R,2R)-trans-2 Aminocyclohexanol hydrochloride, [13374 31 7] C 6 13 FW 151.63 671762 2 (S)-( )-(3 Chloro-2 hydroxypropyl) trimethylammonium chloride, [101396 91 2] C 6 15 2 FW 188.10 329177 (S)-(+)-2 Amino-1 hexanol, [80696 29 3] C 6 15 FW 117.19 534560 3C (R)-( )-2 Amino-1 hexanol, [80696 28 2] C 6 15 FW 117.19 534552 3C (S)-( )-3-tert-Butylamino- 1,2 propanediol, [30315 46 9] C 7 17 2 FW 147.22 472980 3C C 3 2 2 (R)-( )-2 Amino-1 phenylethanol, [2549 14 6] C 8 11 FW 137.18 494577 (S)-2 Amino-1 phenylethanol, 97.0% (GC, sum of enantiomers) [56613 81 1] C 8 11 FW 137.18 2 2 [636 88 4] C 8 11 3 C 4 6 6 FW 319.26 407453 2 orepinephrine L-bitartrate hydrate, 2 x 2 [339091 66 6] C 8 11 3 C 4 6 6 x 2 FW 319.26 (Anh) 392480 (S)-2-(-amino)-1 propanol, [79069 13 9] C 8 17 3 FW 175.23 469513 3C (1S,2R)-( )-cis-1 Amino-2 indanol, [126456 43 7] C 9 11 FW 149.19 440833 2 (1R,2S)-(+)-cis-1 Amino-2 indanol, [136030 00 7] C 9 11 FW 149.19 440841 2 (1R,2R)-( )-trans-1 Amino-2 indanol, [163061 73 2] C 9 11 FW 149.19 663336 2 [163061 74 3] C 9 11 FW 149.19 663344 (R)-( )-1 Amino-6 hydroxyindan, C 9 11 FW 149.19 675377 (1R,2R)-( )-2 Amino-1-(4 nitrophenyl)-1,3 propanediol, [716 61 0] C 9 12 2 4 FW 212.20 A70704 2 (1S,2S)-(+)-2 Amino-1-(4 nitrophenyl)-1,3 propanediol, [2964 48 9] C 9 12 2 4 FW 212.20 471674 2 (S)-( )-2 Amino-3 phenyl-1 propanol, [3182 95 4] C 9 13 FW 151.21 190438 (R)-(+)-2 Amino-3 phenyl-1 propanol, [5267 64 1] C 9 13 FW 151.21 284491 (1S,2S)-(+)-2 Amino-1 phenyl- 1,3 propanediol, [28143 91 1] C 9 13 2 FW 167.21 186546 2 2 2 2 2 2 2 rganic Building Blocks 09222 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 35

(1R,2R)-( )-2 Amino-1 phenyl- 1,3 propanediol, (1S,2S)-trans---2 aminocyclopentanol (R)-( )-2-tert-Butylamino-1 phenylethanol, rganic Building Blocks [46032 98 8] C 9 13 2 FW 167.21 248886 2 (S)-(+)-2 Amino-3 cyclohexyl-1 propanol hydrochloride, [117160 99 3] C 9 19 FW 193.71 432261 2 --(S)-( )-2 amino-1 butanol, 96% [150736 72 4] C 9 19 3 FW 189.25 660116 3C [145106 43 0] C 10 19 3 FW 201.26 671436 (1R,2R)-trans---2 aminocyclopentanol, 98.5% (GC) [454170 16 2] C 10 19 3 FW 201.26 671312 (S)-( )-2-(-amino)-1,5 pentanediol, [162955 48 8] C 10 21 4 FW 219.28 536644 [14467 51 7] C 12 19 FW 193.29 551953 C 3 C 3 (S)-(+)-2-tert-Butylamino-1 phenylethanol, [14467 32 4] C 12 19 FW 193.29 551961 (S)-(+)-2 Amino-2-(4-tert-butylphenyl)ethanol, C 12 19 FW 193.29 3C 3C C 3 C 3 2 --(R)-(+)-2 amino-1 butanol, 96% C 9 19 3 FW 189.25 660108 3C (S)-( )-2-(-amino)-1,4 butanediol, [128427 10 1] C 9 19 4 FW 205.25 536652 (1S,2S)-(+)-2 Amino-3 methoxy- 1 phenyl-1 propanol, [51594 34 4] C 10 15 2 FW 181.23 316520 C 3 2 (R)-(+)-2 Amino-3 benzyloxy-1 propanol, [58577 87 0] C 10 15 2 FW 181.23 473758 (1S,2S)-(+)-Thiomicamine, [16854 32 3] C 10 15 2S FW 213.30 3CS 2 2 (1S,2S)-trans---2 aminocyclohexanol, [145166 06 9] C 11 21 3 FW 215.29 670987 (1R,2R)-trans---2 aminocyclohexanol, [155975 19 2] C 11 21 3 FW 215.29 670863 --(2S,3S)-( )-2 amino-3 methyl-1 pentanol, 96% [106946 74 1] C 11 23 3 FW 217.31 660205 3C (+)-2 Amino--[(1S,2S)-(2 hydroxy- 1 methyl-2 phenyl)ethyl]-methylacetamide, [170115 96 5] C 12 18 2 2 FW 222.28 516120 3C C 3 2 666130 (1S,2R)-(+)-2 Amino-1,2 diphenylethanol, [23364 44 5] C 14 15 FW 213.28 331880 2 (1R,2S)-( )-2 Amino-1,2 diphenylethanol, [23190 16 1] C 14 15 FW 213.28 331899 2 (S,S)-( )-2 Amino-1,2 diphenylethanol, 99.5% (PLC) [23190 17 2] C 14 15 FW 213.28 671223 2 (R,R)-(+)-2 Amino-1,2 diphenylethanol, 99.5% (PLC) [88082 66 0] C 14 15 FW 213.28 671126 2 361887 36 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(1R,2R)-( )---2 amino-1- (4 nitrophenyl)-1,3 propanediol, 96% [366487 74 3] C 14 20 2 6 FW 312.32 660213 2 cis-(1s,2r)-( )-2-(Benzylamino) cyclohexanemethanol, [71581 93 6] C 14 21 FW 219.32 (R)-( )-2 Benzylamino-1 phenylethanol, [107171 75 5] C 15 17 FW 227.30 551988 (S)-(+)-2 Benzylamino-1 phenylethanol, [51096 49 2] C 15 17 FW 227.30 551996 (S)-( )-2 Amino-4 methyl-1,1 diphenyl-1 pentanol, [78603 97 1] C 18 23 FW 269.38 554561 2 3C (S)-( )-2 Amino-3,3 dimethyl- 1,1 diphenyl-1 butanol, [144054 70 6] C 18 23 FW 269.38 t-bu 2 rganic Building Blocks 405086 (1S,2S)-(+)---2 amino-1 phenyl-1,3 propanediol, C 14 21 4 FW 267.32 661066 (R)-(+)-Atenolol, 3C [56715 13 0] C 14 22 2 3 FW 266.34 330884 2 (S)-( )-2-(-amino)-3 cyclohexyl- 1 propanol, 90% [103322 56 1] C 14 27 3 FW 257.37 421693 (R)-(+)-2 Amino-1,1 diphenyl- 1 propanol, [78603 93 7] C 15 17 FW 227.30 2 C 3 (R)-(+)-3 Benzyloxy-2-(-amino)- 1 propanol, [127559 33 5] C 15 23 4 FW 281.35 473766 (R)-(+)-2 Amino-3 methyl-1,1 diphenyl-1 butanol, [86695 06 9] C 17 21 FW 255.35 551082 3C 2 (S)-( )-2 Amino-3 methyl-1,1 diphenyl-1 butanol, [78603 95 9] C 17 21 FW 255.35 551015 3C C 3 2 (S)-(+)-2-(Dibenzylamino)-1 propanol, [60479 65 4] C 17 21 FW 255.35 349607 3C 557900 (2R,3S)-( )-4 Dimethylamino- 1,2 diphenyl-3 methyl-2 butanol, [72541 03 8] C 19 25 FW 283.41 517844 Chirald, [38345 66 3] C 19 25 FW 283.41 227404 (S)-2-(,-Dibenzylamino)- 3 methylbutanol, 90% [111060 54 9] C 19 25 FW 283.41 538167 3C Ph Ph (S)-( )-2 Amino-1,1,2 triphenylethanol, [129704 13 8] C 20 19 FW 289.37 2 549460 (S)-( )-2 Amino-1,1 diphenyl-1 propanol, [78603 91 5] C 15 17 FW 227.30 2 C 3 (R)-(+)-2 Amino-4 methyl-1,1 diphenyl-1 pentanol, [161832 74 2] C 18 23 FW 269.38 554553 2 3C 553255 (S)-(+)-2-(,-Dibenzylamino)- 4 methylpentanol, 90% [111060 53 8] C 20 27 FW 297.43 3C C 3 549479 538183 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 37

(R)-(+)-2 Amino-1,1,3 triphenyl- 1 propanol, (R)-(+)--Carbomethoxy-2 amino- 1,1,2 triphenylethanol, (S)-(+)-2-(Dibenzylamino)-3 phenyl-1 propanol, rganic Building Blocks [86906 05 0] C 21 21 FW 303.40 554472 2 (S)-( )-2 Amino-1,1,3 triphenyl- 1 propanol, [79868 78 3] C 21 21 FW 303.40 2 [352535 67 2] C 22 21 3 FW 347.41 554413 (S)-( )--Carboxymethoxy-2 amino-1,1,2 triphenylethanol, C 22 21 3 FW 347.41 [111060 52 7] C 23 25 FW 331.45 421731 554464 554421 Got Chemews? A Monthly Chemistry E-ewsletter from Sigma-Aldrich Visit sigma-aldrich.com/chemnews sigma-aldrich.com 38 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

Aziridines Lithium L-aziridine-2 carboxylate, 97.0% (T, dried material) [67413 27 8] C 3 4 Li 2 FW 93.01 Li + 11558 (S)-1-[(R)-α-Methylbenzyl)aziridine-2 carboxamide, [75985 51 2] C 11 14 2 FW 190.24 570524 3C (R)-1-[(1R)-α-Methylbenzyl]aziridine-2 carboxamide, [75985 52 3] C 11 14 2 FW 190.24 3C Ph 2 2 (S)-1-[(R)-α-Methylbenzyl]aziridine-2 methanol, [173143 73 2] C 11 15 FW 177.24 570532 3C 1 Benzyl 2 methyl (S)-( )-1,2 aziridinedicarboxylate, 96% [104597 98 0] C 12 13 4 FW 235.24 516031 Cbz (S)-(+)-2 Benzyl-1-(p-tolylsulfonyl) aziridine, [62596 64 9] C 16 17 2 S FW 287.38 S Ph ( )-Menthyl (R)-1-[(R)-α-methylbenzyl]aziridine-2 carboxylate, C 21 31 2 FW 329.48 570540 3C 3C ( )-Menthyl (S)-1-[(R)-α-methylbenzyl]aziridine-2 carboxylate, C 21 31 2 FW 329.48 570516 3C 3C C 3 C 3 rganic Building Blocks 570559 464015 C 3 Methyl (S)-( )-1 tritylaziridine- 2 carboxylate, (R)-1-[(R)-α-Methylbenzyl)aziridine-2 methanol, [173034 70 3] C 11 15 FW 177.24 570567 3C Ph [75154 68 6] C 23 21 2 FW 343.42 516015 C 3 Carboxylic Acids (S)-( )-Trifluorolactic acid, (S)-( )-2 Chloropropionic acid, Sodium L-lactate, 99.0% (T) [125995 00 8] C 3 3F 3 3 FW 144.05 F3C [29617 66 1] C 3 5 2 FW 108.52 3C [867 56 1] C 3 5a 3 FW 112.06 3C a 532509 306797 71718 (R)-(+)-2 Bromopropionic acid, 98.0% (GC, sum of enantiomers) [10009 70 8] C 3 5 Br 2 FW 152.97 18165 3C Br (S)-( )-2 Bromopropionic acid, [32644 15 8] C 3 5 Br 2 FW 152.97 385514 3C Br (R)-(+)-2 Chloropropionic acid, [7474 05 7] C 3 5 2 FW 108.52 306800 3C Sodium D-lactate, 99.0% (T) [920 49 0] C 3 5 a 3 FW 112.06 71716 3C a L-( )-Glyceric acid hemicalcium salt monohydrate, (KT) [6057 35 8] C 3 5 4 0.5Ca 2 FW 143.12 372412 2 Ca 2 2 2 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 39

rganic Building Blocks L-(+)-2 Amino-3 phosphonopropionic acid [23052 80 4] C 3 8 5 P FW 169.07 A154 Potassium L-tartrate, [921 53 9] C 4 4 K 2 6 2 FW 244.28 289949 K P L-( )-Malic acid disodium salt, 95 100% (enzymatic) [138 09 0] C 4 4a 2 5 FW 178.05 a 2 K 2 a L-( )-Malic acid, [97 67 6] C 4 6 5 FW 134.09 112577 D-(+)-Malic acid, 97.0% (PLC, sum of enantiomers) [636 61 3] C 4 6 5 FW 134.09 02300 D-( )-Tartaric acid, [147 71 7] C 4 6 6 FW 150.09 483796 (S)-3 ydroxybutyric acid, 97.0% (T) [6168 83 8] C 4 8 3 FW 104.10 54925 3C (S)-(+)-4 Amino-3 hydroxybutyric acid, [7013 05 0] C 4 9 3 FW 119.12 542946 2 (S)-( )-4 Amino-2 hydroxybutyric acid, 96% [40371 51 5] C 4 9 3 FW 119.12 2 M9138 L-Malic acid disodium salt monohydrate, [207511 06 6] C 4 4 a 2 5 2 FW 196.07 233935 a a 2 Potassium L-tartrate monobasic, [868 14 4] C 4 5K 6 FW 188.18 243531 Potassium D-tartrate monobasic [57341 16 9] C 4 5 K 6 FW 188.18 T2032 L-( )-Malic acid sodium salt, 95 100% (enzymatic) [68303 40 2] C 4 5 a 5 FW 156.07 M1125 K + - Sodium hydrogentartrate, [526 94 3] C 4 5a 6 FW 172.07 K a a L-(+)-Tartaric acid, [87 69 4] C 4 6 6 FW 150.09 T109 (R)-( )-3 ydroxybutyric acid sodium salt [13613 65 5] C 4 7 a 3 FW 126.09 298360 3C Sodium (S)-3 hydroxybutyrate, ~ [127604 16 4] C 4 7a 3 FW 126.09 3145 3C (S)-(+)-2 Amino-4 bromobutyric acid hydrobromide, [15159 65 6] C 4 8Br 2 Br FW 262.93 476986 (R)-3 ydroxybutyric acid, 98.0% (T) [625 72 9] C 4 8 3 FW 104.10 54920 Br a a Br 2 3C 467359 (S)-( )-2 Formamidosuccinic anhydride, 90% [33605 73 1] C 5 5 4 FW 143.10 421588 (R)-(+)-Methylsuccinic acid, [3641 51 8] C 5 8 4 FW 132.11 415596 C 3 (S)-( )-Methylsuccinic acid, [2174 58 5] C 5 8 4 FW 132.11 415618 (S)-( )-2 Acetoxypropionic acid, 95% [6034 46 4] C 5 8 4 FW 132.11 453382 (R)-( )-Citramalic acid, [6236 10 8] C 5 8 5 FW 148.11 329142 3C C 3 289981 40 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(R)-(+)-2 Bromo-3 methylbutyric acid, 96% (S)-( )-2-(Trifluoroacetamido)succinic anhydride, (S)-( )-2 ydroxyisocaproic acid, [76792 22 8] C 5 9 Br 2 FW 181.03 468347 3C C 3 (S)-( )-2 Bromo-3 methylbutyric acid, 96% [26782 75 2] C 5 9 Br 2 FW 181.03 462101 3C Br C 3 (S)-2 Chloro-3 methylbutyric acid, 90% (GC) [26782 74 1] C 5 9 2 FW 136.58 25113 Br 3C (R)-2 Chloro-3 methylbutyric acid, 90% (GC) [84918 96 7] C 5 9 2 FW 136.58 25112 3C (S)-(+)-2 Methylbutyric acid, [1730 91 2] C 5 10 2 FW 102.13 245526 3C C 3 (S)-(+)-2 ydroxy-3 methylbutyric acid, [777 33 3] C 6 4 F 3 4 FW 211.10 305251 (S)-( )-2 Acetoxysuccinic anhydride, [59025 03 5] C 6 6 5 FW 158.11 422800 (R)-(+)-2 Acetoxysuccinic anhydride, 96% [79814 40 7] C 6 6 5 FW 158.11 441570 CF3 C 3 (+)-Potassium D s -threo-isocitrate monobasic, 98.0% (T) [20226 99 7] K C 6 7 K 7 FW 230.21 58790 Calcium L-lactate hydrate, 98.0% (KT, calc. based on dry substance) [41372 22 9] C 6 10 Ca 6 x 2 FW 218.22 (Anh) 21185 3C 2 Ca 2+ x2 [13748 90 8] C 6 12 3 FW 132.16 219827 3C (S)-(+)-2,2 Dimethyl-5 oxo-1,3 dioxolane-4 acetic acid, 95% [73991 95 4] C 7 10 5 FW 174.15 445584 3C C 3 (R)-( )-2,2 Dimethyl-5 oxo-1,3 dioxolane-4 acetic acid, 95% [113278 68 5] C 7 10 5 FW 174.15 460028 3C C 3 (R)-( )-2 Chloromandelic acid, [52950 18 2] C 8 7 3 FW 186.59 478873 (S)-(+)-2 Chloromandelic acid, [52950 19 3] C 8 7 3 FW 186.59 562823 (R)-( )-3 Chloromandelic acid, rganic Building Blocks [17407 55 5] C 5 10 3 FW 118.13 379093 D-α-ydroxyisovaleric acid, 98.0% (T) 3C C 3 Magnesium L-lactate hydrate, 95.0% (KT, calc. based on dry substance) [18917 93 6] C 6 10 Mg 6 x 2 FW 202.45 (Anh) 2 Mg 2+ x2 [61008 98 8] C 8 7 3 FW 186.59 445444 (R)-( )-Mandelic acid, [17407 56 6] C 5 10 3 FW 118.13 55452 C 3 3C 63097 (S)-( )-2 ydroxy-3,3 dimethylbutyric acid, [21641 92 9] C 6 12 3 FW 132.16 410918 t-bu [611 71 2] C 8 8 3 FW 152.15 154210 (S)-(+)-Mandelic acid, [17199 29 0] C 8 8 3 FW 152.15 M2004 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 41

(+)-, -Diacetyl-L-tartaric anhydride, (R)-( )-α-methoxyphenylacetic acid, (S)-( )-α-methoxy-α-(trifluoromethyl)phenylacetic acid, rganic Building Blocks [6283 74 5] C 8 8 7 FW 216.14 358924 3C (R)-( )-exahydromandelic acid, [53585 93 6] C 8 14 3 FW 158.19 301140 (S)-(+)-exahydromandelic acid, [3966 32 3] C 9 10 3 FW 166.17 248967 (S)-(+)-α-Methoxyphenylacetic acid [26164 26 1] C 9 10 3 FW 166.17 248983 (S)-3 ydroxy-3 phenylpropionic acid, 98.0% (GC, sum of enantiomers) C 3 [17257 71 5] C 10 9 F 3 3 FW 234.17 318035 (R)-(+)-α-Methoxy-α-trifluoromethylphenylacetic acid, [20445 31 2] C 10 9F 3 3 FW 234.17 155268 3C CF 3 3C CF3 (S)-( )-α-methoxy-α-(trifluoromethyl)phenylacetic acid, [61475 31 8] C 8 14 3 FW 158.19 [36567 72 3] C 9 10 3 FW 166.17 [17257 71 5] C 10 9F 3 3 FW 234.17 3C CF3 301159 56193 155616 (S)-2 Bromo-3 phenylpropionic acid, 95.0% (T) [35016 63 8] C 9 9 Br 2 FW 229.07 00031 Br (R)-(+)-2-(4 ydroxyphenoxy)propionic acid, [94050 90 5] C 9 10 4 FW 182.17 474533 (R)-( )-α-acetylmandelic acid, [51019 43 3] C 10 10 4 FW 194.18 253030 3C (S)-(+)-2 Phenylpropionic acid, [7782 24 3] C 9 10 2 FW 150.17 279900 (1S,2R)-1 Methyl cis-1,2,3,6 tetrahydrophthalate, [88335 93 7] C 9 12 4 FW 184.19 (S)-(+)--Acetylmandelic acid, [7322 88 5] C 10 10 4 FW 194.18 253022 3C (R)-( )-2 Phenylpropionic acid, [7782 26 5] C 9 10 2 FW 150.17 279897 L-( )-3 Phenyllactic acid, 367281 [1S-(1β,2α,3β)]-(+)-3 Methyl-2- (nitromethyl)-5 oxocyclopentaneacetic acid, [123000 45 3] C 9 13 5 FW 215.20 2 (R)-( )-Phenylsuccinic acid, 96.0% (PLC, sum of enantiomers) [46292 93 7] C 10 10 4 FW 194.18 78172 [20312 36 1] C 9 10 3 FW 166.17 113069 D-(+)-3 Phenyllactic acid, [7326 19 4] C 9 10 3 FW 166.17 647497 C 3 Aluminum L-lactate, 98 102% (related on reference to anhydrous substance) [18917 91 4] C 9 15 Al 9 FW 294.19 3C - Al 3+ 3 (S)-(+)-Phenylsuccinic acid, 99.0% (PLC, sum of enantiomers) [4036 30 0] C 10 10 4 FW 194.18 78173 376906 25301 42 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(S)-( )-2-(Phenylcarbamoyloxy)propionic acid, [102936 05 0] C 10 11 4 FW 209.20 328243 (R)-( )-2 Phenylbutyric acid, [938 79 4] C 10 12 2 FW 164.20 279870 3C (S)-(+)-2 Phenylbutyric acid, [4286 15 1] C 10 12 2 FW 164.20 279889 3C (R)-3 Phenylbutyric acid, 98.5% (GC, sum of enantiomers) [772 14 5] C 10 12 2 FW 164.20 78239 C 3 (S)-3 Phenylbutyric acid, 99.0% (PLC, sum of enantiomers) (S)-2 ydroxy-2 phenylbutyric acid, 96% [24256 91 5] C 10 12 3 FW 180.20 676691 3C Ph (R)-2 ydroxy-4 phenylbutyric acid, [29678 81 7] C 10 12 3 FW 180.20 420085 (S,S)-Ethylenediamine-, -disuccinic acid trisodium salt solution [178949 82 1] C 10 13 2 a 3 8 FW 358.19-92698 (S)-( )-Perillic acid, 95% [23635 14 5] C 10 14 2 FW 166.22 218359 - a + - 2C (1S)-(+)-Ketopinic acid, a + a+ (1R,3S)-(+)-Camphoric acid, [124 83 4] C 10 16 4 FW 200.23 C409 C 3 3C (1S,3R)-( )-Camphoric acid, [560 09 8] C 10 16 4 FW 200.23 376345 (R)-(+)-Citronellic acid, [18951 85 4] C 10 18 2 FW 170.25 340499 3C (S)-( )-Citronellic acid, [2111 53 7] C 10 18 2 FW 170.25 364428 3C C 3 3C C 3 (S)-(+)-2 Methylbutyric anhydride, 94% [84131 91 9] C 10 18 3 FW 186.25 3C C 3 C 3 rganic Building Blocks [772 15 6] C 10 12 2 FW 164.20 78240 (R)-(+)-2-(Benzyloxy)propionic acid, 97.0% (PLC) [100836 85 9] C 10 12 3 FW 180.20 C 3 [40724 67 2] C 10 14 3 FW 182.22 420964 (1S)-( )-Camphanic acid, [13429 83 9] C 10 14 4 FW 198.22 3C 3C 348562 (R)-3-(-amino)-5-hexynoic acid, [332064 91 2] C 11 17 4 FW 227.26 711942 C (S)-3-(-amino)-5-hexynoic acid, 8 8 00696 (R)-2 ydroxy-2 phenylbutyric acid, 96% [3966 31 2] C 10 12 3 FW 180.20 676705 3C Ph 328227 (+)-trans-chrysanthemic acid, 98.0% (GC) [4638 92 0] C 10 16 2 FW 168.23 18509 3C 3C 3C C 3 [270596 47 9] C 11 17 4 FW 227.26 711934 C (R)-3-(-amino)-5-hexenoic acid, [269726 94 5] C 11 19 4 FW 229.27 711969 2C 8 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 43

rganic Building Blocks (S)-3-(-amino)-5-hexenoic acid, [270263 03 1] C 11 19 4 FW 229.27 711950 2C 8 (R)-(+)--(1 Phenylethyl)succinamic acid, [21752 33 0] C 12 15 3 FW 221.25 461423 (S)-( )--(1 Phenylethyl)succinamic acid, [21752 34 1] C 12 15 3 FW 221.25 461431 (+)-Menthyloxyacetic acid, [94133 41 2] C 12 22 3 FW 214.30 448397 3C (R)-α-Methoxy-2 naphthylacetic acid, 99.0% [156942 67 5] C 13 12 3 FW 216.23 669865 (S)-α-Methoxy-2 naphthylacetic acid, [157134 51 5] C 13 12 3 FW 216.23 669989 C 3 (R)-( )-6 Methoxy-α-methyl- 2 naphthaleneacetic acid, [23979 41 1] C 14 14 3 FW 230.26 570842 aproxen, [22204 53 1] C 14 14 3 FW 230.26 284785 3C 3C C 3 C 3 (R)-( )-α-[(3 Ethoxy-1 methyl- 3 oxo-1 propenyl)amino]benzeneacetic acid potassium salt, [961 69 3] C 14 16 K 4 FW 301.38 K (S)-(+)-Z-4 Amino-2 hydroxybutyric acid, [40371 50 4] C 12 15 5 FW 253.25 533106 Cbz (R)-(+)-3 ydroxy-5 oxo-1 cyclopentene-1 heptanoic acid, 96% [54996 33 7] C 12 18 4 FW 226.27 473057 [1R-(2-endo,3-exo)]-3 ydroxy- 4,7,7 trimethylbicyclo[2.2.1]heptane-2 acetic acid, [81925 04 4] C 12 20 3 FW 212.29 309664 3C C 3 3C ( )-Menthyloxyacetic acid, [40248 63 3] C 12 22 3 FW 214.30 M3000 3C (R)-(+)-α-[(3 Methoxy-1 methyl- 3 oxo-1 propenyl)amino]-1,4 cyclohexadiene-1 acetic acid sodium salt, [26774 89 0] C 13 16 a 4 FW 273.26 471631 (S)-(+)-Ibuprofen, [51146 56 6] C 13 18 2 FW 206.28 375160 3C 3C a C 3 (S)-2-(-amino)octanedioic acid, [66713 87 9] C 13 23 6 FW 289.32 671983 (R)-2-(-amino)octanedioic acid, [75113 71 2] C 13 23 6 FW 289.32 471666 (1R,2S)-( )-2 Benzamidocyclohexanecarboxylic acid, [26693 55 0] C 14 17 3 FW 247.29 568090 (1S,2R)-(+)-2 Benzamidocyclohexanecarboxylic acid, [26685 82 5] C 14 17 3 FW 247.29 568104 (+)-, -Di-pivaloyl-D-tartaric acid, 98.0% (T) [76769 55 6] C 14 22 8 FW 318.32 43456 t-bu t-bu 672092 44 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

( )-, -Di-pivaloyl-L-tartaric acid, 98.0% (T) [65259 81 6] C 14 22 8 FW 318.32 43457 t-bu (R)-( )-2 Fluoro-α-methyl- 4 biphenylacetic acid, [51543 40 9] C 15 13 F 2 FW 244.26 F t-bu C 3 (S)-( )--(1 Phenylethyl)phthalamic acid, [21752 36 3] C 16 15 3 FW 269.30 461466 (S)-( )--[1-(1 aphthyl)ethyl]succinamic acid, [212556 04 2] C 16 17 3 FW 271.31 Rosmarinic acid, [20283 92 5] C 18 16 8 FW 360.31 536954 ( )-mono-(1r)-menthyl phthalate, [33744 74 0] C 18 24 4 FW 304.38 3C C 3 rganic Building Blocks 545740 461644 448443 (S)-(+)-2 Fluoro-α-methyl- 4 biphenylacetic acid, [51543 39 6] C 15 13 F 2 FW 244.26 F C 3 (R)-(+)--[1-(1 aphthyl)ethyl]succinamic acid, [78681 09 1] C 16 17 3 FW 271.31 Ricinoleic acid, ~80% (GC) [141 22 0] C 18 34 3 FW 298.46 (C 2)5 482641 83903 (R)-2-[(-amino)methyl]-3- phenylpropionic acid, [262301 38 2] C 15 21 4 FW 279.33 698660 8 461636 (+)-2,3 Dibenzoyl-D-tartaric acid, [17026 42 5] C 18 14 8 FW 358.30 Ph Ph L-Lactic acid tetrabutylammonium salt solution 3C 3C C 19 41 3 FW 331.53 69784 C 3 3C (S)-2-[(-amino)methyl]-3- phenylpropionic acid, [189619 55 4] C 15 21 4 FW 279.33 697680 8 163449 Dibenzoyl-L-tartaric acid, [2743 38 6] C 18 14 8 FW 358.30 (S)-(+)--[1-(1 aphthyl)ethyl] phthalamic acid, [163438 06 0] C 20 17 3 FW 319.35 C 3 (S)-(+)-Ketoprofen, 345849 399736 [22161 81 5] C 16 14 3 FW 254.28 ( )-, -Dibenzoyl-L-tartaric acid monohydrate, 99.0% (T) (R)-( )--[1-(1 aphthyl)ethyl] phthalamic acid, 471909 (R)-(+)--(1 Phenylethyl)phthalamic acid, [21752 35 2] C 16 15 3 FW 269.30 [62708 56 9] C 18 14 8 2 FW 376.31 33622 2 [163438 05 9] C 20 17 3 FW 319.35 399728 461458 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 45

(+)-, -Di-p-toluoyl-D-tartaric acid, Di-p-toluoyl-D-tartaric acid monohydrate,,-bis[(s)-( )-1 phenylethyl] phthalamic acid, rganic Building Blocks 3C [32634 68 7] C 20 18 8 FW 386.35 302813 ( )-, -Di-p-toluoyl-L-tartaric acid, 3C [32634 66 5] C 20 18 8 FW 386.35 3C [71607 31 3] C 20 18 8 2 FW 404.37 108081 2,-Bis[(R)-(+)-1 phenylethyl] phthalamic acid, [312619 40 2] C 24 23 3 FW 373.44 461679 3C C 3 C 24 23 3 FW 373.44 461687 3C 371416 46 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(R)-(+)- and (S)-( )-Stericol : ew, Effective Chiral Auxiliaries The introduction of chirality to organic molecules through the use of auxiliaries is a basic strategy in organic chemistry. Chiral benzylic alcohols are of particular interest because they often afford useful levels of stereoselection and are generally easy to cleave. The enantiomers of 1-(2,4,6-triisopropyl)phenylethanol ((R)- and (S)-Stericol ) are especially beneficial as chiral auxiliaries, providing high diasteromeric ratios in [2+2] cycloadditions, 1 oxidations, 2 and carbon-carbon bond forming reactions. 3 Preparation of Dichlorocyclobutanones i-pr i-pr i-pr C 3 i-pr 1) K, 2 C=C n-buli, RI 2) LiAl 4 3 C Ar R up to 19:1 dr Ar = 2,4,6-(i-Pr) 3 C 6 2 i-pr i-pr C 3 i-pr R Lactones Cyclopentanones Amino Acids Alkaloids Asymmetric xidation of Benzenesulfenates i-pr i-pr C 3 P(i-Pr) 2 S i-pr S C 4, rt i-pr i-pr C 3 i-pr S * up to 13:1 dr Preparation of β,γ-unsaturated Silyl Sulfinates i-pr C P(i-Pr) 2 i-pr i-pr C 3 (R)-(+)-1-(2,4,6-Triisopropylphenyl)ethanol C 17 28 248.40 [181531-14-6] 672599 i-pr i-pr i-pr C 3 (S)-( )-1-(2,4,6-Triisopropylphenyl)ethanol C 17 28 248.40 [102225-88-7] 672483 References: (1) (a) de Azevedo, M. B. M.; Greene, A. E. J. rg. Chem. 1995, 60, 4940. (b) Kanazawa, A. et al. J. Chem. Soc. Perkin Trans. 1997,1911. (c) ebois, P.; Greene, A. E. J. rg. Chem. 1996, 61, 5210. (d) Ceccon, J. et al. Synlett 2005, 1413. (e) Roche, C. et al. rg. Lett. 2003, 5, 1741. (f) Muniz, M.. et al. Synlett 2005, 1328. (g) Roche, C. et al. J. rg. Chem. 2005, 70, 8352. (h) Ceccon, J. et al. rg. Lett. 2006, 8, 4739. (2) amel, M.; Grach, G.; Abrunhosa, I.; Gulea, M.; Masson, S.; Vazeux, M.; Drabowicz, J.; Mikolajczyk, M. Tetrahedron: Asymmetry 2005, 16, 3406. (3) (a) arkevitch, V. et al. Angew. Chem., Int. Ed. 2000, 39, 1806. (b) Bouchez, L. C. et al. Tetrahedron 2005, 61, 11473. (c) arkevitch, V. et al. J. rg. Chem. 2001, 66, 5080. i-pr i-pr C 3 i-pr TMS Yb(Tf) 3, S 2 C 3 + R C 2 C2 2, -90 C i-pr i-pr C 3 S 2 TMS R C 3 up to 25:1 dr sigma-aldrich.com

Cyanides/itriles rganic Building Blocks (R)-(+)-4 Chloro-3 hydroxybutyronitrile, [84367 31 7] C 4 6 FW 119.55 456152 (S)-(+)-2 Methylbutyronitrile, [25570 03 0] C 5 9 FW 83.13 247308 3C (R)-(+)-4 Chloromandelonitrile, [97070 79 6] C 8 6 FW 167.59 469742 (R)-(+)-Mandelonitrile, [10020 96 9] C 8 7 FW 133.15 469653 C C C C (R)-2 Acetoxy-3,3 dimethylbutyronitrile, 99.0% (GC, sum of enantiomers) [126567 38 2] C 8 13 2 FW 155.19 00851 3C (R)-(+)-4 Methylmandelonitrile, [10017 04 6] C 9 9 FW 147.17 469734 3C (R)-(+)-4 Methoxymandelonitrile, [97070 73 0] C 9 9 2 FW 163.17 469688 3C C (R)-α-Acetoxyphenylacetonitrile, 97.0% (GC, sum of enantiomers) [119718 89 7] C 10 9 2 FW 175.18 C t-bu C C C 3 tert-butyl (4R,6R)-6 cyanomethyl- 2,2 dimethyl-1,3 dioxane-4 acetate, [125971 94 0] C 14 23 4 C FW 269.34 539015 3C,-Bis(4 methoxybenzyloxy- carbonyl)-(s)-2 amino-3- (4 hydroxyphenyl)propionitrile, 96% 3C [73148 72 8] C 27 26 2 7 FW 490.50 370126 3C C 00873 Epoxides (S)-( )-3,3,3 Trifluoro-1,2 epoxypropane, [130025 34 2] C 3 3 F 3 FW 112.05 F3C (S)-(+)-Epichlorohydrin, [67843 74 7] C 3 5 FW 92.52 540080 (S)-( )-Glycidol, [60456 23 7] C 3 6 2 FW 74.08 474789 665797 (R)-(+)-3,3,3 Trifluoro-1,2 epoxypropane, [143142 90 9] C 3 3 F 3 FW 112.05 667005 (R)-( )-Epichlorohydrin, [51594 55 9] C 3 5 FW 92.52 F3C (R)-(+)-Propylene oxide, [15448 47 2] C 3 6 FW 58.08 540048 (S)-( )-Propylene oxide, [16088 62 3] C 3 6 FW 58.08 540021 3C 3C (R)-(+)-Glycidol, [57044 25 4] C 3 6 2 FW 74.08 480819 (R)-2 Vinyloxirane, 95.0% (GC, sum of enantiomers) [62249 81 4] C 4 6 FW 70.09 08011 C 2 540072 48 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(S)-3,4 Epoxy-1 butene, 90% (GC) [62249 80 3] C 4 6 FW 70.09 19377 Methyl (2S)-glycidate, [118712 39 3] C 4 6 3 FW 102.09 469432 Methyl (2R)-glycidate, [111058 32 3] C 4 6 3 FW 102.09 469424 (S)-( )-(2 Bromoethyl)oxirane, 90% (GC, sum of enantiomers) C 2 Ethyl (S)-2 oxiranylacetate, 96.0% (GC, sum of enantiomers) [112083 63 3] C 6 10 3 FW 130.14 51241 (R)-(+)-1,2 Epoxyhexane, [104898 06 8] C 6 12 FW 100.16 477087 C 3(C 2) 2C 2 (S)-(+)-Glycidyl butyrate, [65031 96 1] C 7 12 3 FW 144.17 460508 (R)-( )-Glycidyl butyrate, 96% (S)-2-(4 itrophenyl)oxirane, 98.0% (GC) [78038 42 3] C 8 7 3 FW 165.15 75914 (R)-2-(4 itrophenyl)oxirane, 96.0% (GC) [78038 43 4] C 8 7 3 FW 165.15 69167 (R)-(+)-Styrene oxide, [20780 53 4] C 8 8 FW 120.15 540099 2 2 rganic Building Blocks [61847 07 2] C 4 7 Br FW 151.00 16995 (S)-4 Chloro-1,2 epoxybutane, 98.0% (GC, sum of enantiomers) Br [60456 26 0] C 7 12 3 FW 144.17 338125 (R)-(+)-1,2 Epoxyheptane, 97.0% (GC, sum of enantiomers) (S)-( )-Styrene oxide, [20780 54 5] C 8 8 FW 120.15 540102 [948594 94 3] C 4 7 FW 106.55 29177 (S)-( )-1,2 Epoxybutane, [30608 62 9] C 4 8 FW 72.11 532363 (R)-(+)-1,2 Epoxybutane, [3760 95 0] C 4 8 FW 72.11 532355 3C 3C (R)-( )-Glycidyl methyl ether, [64491 70 9] C 4 8 2 FW 88.11 454680 (S)-(+)-Glycidyl methyl ether, [64491 68 5] C 4 8 2 FW 88.11 454699 C 3 [110549 07 0] C 7 14 FW 114.19 49671 (R)-(+)-3 Chlorostyrene oxide [62600 71 9] C 8 7 FW 154.59 563382 (S)-(4 Fluorophenyl)oxirane, 95.0% (GC) [134356 74 4] C 8 7 F FW 138.14 76477 (R)-(4 Fluorophenyl)oxirane, 90.0% (GC) [134356 73 3] C 8 7F FW 138.14 41609 C 2(C 2) 3C 3 F F (2R,3R)-Diethyl 2,3 epoxysuccinate, 96% [74243 85 9] C 8 12 5 FW 188.18 586250 3C C 3 (S)---2,3 epoxypropylamine, [161513 47 9] C 8 15 3 FW 173.21 672033 (R)-(+)-1,2 Epoxyoctane, [77495 66 0] C 8 16 FW 128.21 477109 (C2)4C2 (2S,3S)-( )-3-(4 itrophenyl)glycidol, [1885 07 0] C 9 9 4 FW 195.17 300500 2 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 49

rganic Building Blocks (R)-( )-Glycidyl 3 nitrobenzenesulfonate, 97.0% (GC) [115314 17 5] C 9 9 6 S FW 259.24 50047 S (S)-(+)-Glycidyl 3 nitrobenzenesulfonate, 99.0% (GC) [115314 14 2] C 9 9 6 S FW 259.24 50048 S (1S,2S)-( )-1 Phenylpropylene oxide, [4518 66 5] C 9 10 FW 134.18 287792 3C (1R,2R)-(+)-1 Phenylpropylene oxide, [14212 54 5] C 9 10 FW 134.18 277037 3C (2S,3S)-( )-3 Phenylglycidol, [104196 23 8] C 9 10 2 FW 150.17 300489 (S)-2 xiranylanisole, 97.0% (GC, sum of enantiomers) 2 2 [3aS-(3aα,5aβ,6aβ,6bα)]-4 Bromo- 3a,5a,6a,6b-tetrahydro- 2,2 dimethyloxireno[e]-1,3 benzodioxole, [130669 74 8] C 9 11Br 3 FW 247.09 490857 [3aR-(3aα,5aβ,6aβ,6bα)]- 3a,5a,6a,6b-Tetrahydro- 2,2 dimethyloxireno[e]-1,3 benzodioxole, 96% [145107 27 3] C 9 12 3 FW 168.19 490881 Br C 3 C 3 tert-butyldimethylsilyl (R)-( )-glycidyl ether, [124150 87 4] C 9 20 2 Si FW 188.34 684333 C 3 t-bu Si tert-butyldimethylsilyl (S)-(+)-glycidyl ether, [123237 62 7] C 9 20 2Si FW 188.34 684325 C 3 t-bu Si C 3 (S)-(+)-Glycidyl benzyl ether, [16495 13 9] C 10 12 2 FW 164.20 363537 (2S)-(+)-Glycidyl tosylate, [70987 78 9] C 10 12 4S FW 228.26 540129 S ( )-Limonene oxide, mixture of cis and trans, C 10 16 FW 152.23 218332 3C 2C (+)-Limonene oxide, mixture of cis and trans, [1195 92 2] C 10 16 FW 152.23 218324 3C 3C (+)-Limonene 1,2 epoxide, 97.0% (GC, sum of isomers) [203719 54 4] C 10 16 FW 152.23 17763 C 2 3C 3C (R)-(+)-1,2 Epoxy-9 decene, [137310 67 9] C 10 18 FW 154.25 477281 C2 C2 [71031 03 3] C 9 10 2 FW 150.17 04855 (R)-2 xiranylanisole (R)-( )-Glycidyl benzyl ether, [14618 80 5] C 10 12 2 FW 164.20 363529 (2R)-( )-Glycidyl 4 nitrobenzoate, [106268 95 5] C 10 9 5 FW 223.18 2 [71031 02 2] C 9 10 2 FW 150.17 29438 (2R)-( )-Glycidyl tosylate, [113826 06 5] C 10 12 4S FW 228.26 540110 S 300438 (2S)-(+)-Glycidyl 4 nitrobenzoate, [115459 65 9] C 10 9 5 FW 223.18 2 300446 50 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(2S)-(+)-2 Methylglycidyl 4 nitrobenzoate, [118200 96 7] C 11 11 5 FW 237.21 305766 2 (2R)-( )-2 Methylglycidyl 4 nitrobenzoate, [106268 96 6] C 11 11 5 FW 237.21 305758 2 (2S,3S)-trans-3 Methyloxirane- 2 methyl 4 nitrobenzoate, 97.0% (PLC, sum of enantiomers) [106268 97 7] C 11 11 5 FW 237.21 68249 3C 2 (R)-(+)-1,2 Epoxydodecane, [109856 85 1] C 12 24 FW 184.32 477141 C 2(C 2) 8C 3 (R)-(+)-1,2 Epoxytridecane, [59829 81 1] C 13 26 FW 198.34 477168 C2(C2)9 (2 S,3 S)-4 -Bromo-cis-2,3 -epoxybutyl (1S)-10 camphorsulfonate, [343338 27 2] C 14 21 Br 5 S FW 381.28 510785 Br 3C S (R)-(+)-1,2 Epoxytetradecane, (2R,3S)-(+)-3-(Benzyloxymethyl)oxirane-2 methanol 4 nitrobenzoic acid ester, 99.0% (PLC, sum of enantiomers) [78469 86 0] C 18 17 6 FW 343.33 13730 2 (2S,3R)-( )-3-(Benzyloxymethyl)oxirane-2 methanol 4 nitrobenzoic acid ester, 99.0% (PLC, sum of enantiomers) [78513 08 3] C 18 17 6 FW 343.33 13732 2 rganic Building Blocks (R)-( )--(2,3 Epoxypropyl)phthalimide, 99.0% (GC) [181140 34 1] C 11 9 3 FW 203.19 671711 (S)-(+)--(2,3 Epoxypropyl)phthalimide, 99.0% (GC) [161596 47 0] C 11 9 3 FW 203.19 671606 (2R)-(+)-3,3 Dimethylglycidyl 4 nitrobenzoate, [116619 64 8] C 14 28 FW 212.37 477176 C2(C2)10 (2S,3S)-1,2 Epoxy-3-(-amino)- 4 phenylbutane, [98737 29 2] C 15 21 3 FW 263.33 476951 (R)-(+)-1,2 Epoxypentadecane, [96938 06 6] C 15 30 FW 226.40 477184 C2(C2)11 (R)-(+)-Glycidyl trityl ether, [65291 30 7] C 22 20 2 FW 316.39 453455 (S)-( )-Glycidyl trityl ether, [129940 50 7] C 22 20 2 FW 316.39 456268 [141700 91 6] C 12 13 5 FW 251.24 2 C 3 C 3 300535 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 51

Esters (+)-Methyl (R)-2 chloropropionate, Methyl (S)-(+)-3 hydroxybutyrate, Ethyl (R)-(+)-4,4,4 trifluoro- 3 hydroxybutyrate, rganic Building Blocks [77287 29 7] C 4 7 2 FW 122.55 277754 3C ( )-Methyl (S)-2 chloropropionate, [73246 45 4] C 4 7 2 FW 122.55 247030 ( )-Methyl L-lactate, [27871 49 4] C 4 8 3 FW 104.10 230340 (+)-Methyl D-lactate, [17392 83 5] C 4 8 3 FW 104.10 277762 3C 3C C 3 ( )-Methyl (S)-3 bromo-2 methylpropionate, [98190 85 3] C 5 9Br 2 FW 181.03 324922 Br [53562 86 0] C 5 10 3 FW 118.13 243167 3C Methyl (R)-( )-3 hydroxy-2 methylpropionate, [72657 23 9] C 5 10 3 FW 118.13 270148 C 3 Methyl (S)-(+)-3 hydroxy-2 methylpropionate, [80657 57 4] C 5 10 3 FW 118.13 270121 ( )-Ethyl L-lactate, [687 47 8] C 5 10 3 FW 118.13 E34102 C 3 C 3 3C (+)-Ethyl D-lactate, 99.0% (GC, sum of enantiomers) [7699 00 5] C 5 10 3 FW 118.13 69796 3C C 3 C 3 [85571 85 3] C 6 9 F 3 3 FW 186.13 376795 F3C Ethyl (R)-2-(trifluoromethylsulfonyloxy)propionate, 97.0% ( 19 F -MR) [84028 89 7] C 6 9F 3 5S FW 250.19 91724 F3C S Ethyl (S)-2-(trifluoromethylsulfonyloxy)propionate, 96% [84028 88 6] C 6 9F 3 5S FW 250.19 374636 F3C S (R)-(+)-2 Methylsuccinic acid 4 methyl ester, 95% [81025 83 4] C 6 10 4 FW 146.14 546720 Dimethyl (S)-( )-malate, [617 55 0] C 6 10 5 FW 162.14 3C C 3 3C C 3 Methyl (R)-(+)-3 bromo-2 methylpropionate, [110556 33 7] C 5 9 Br 2 FW 181.03 325090 Methyl (R)-3 hydroxybutyrate, [3976 69 0] C 5 10 3 FW 118.13 243159 Br 3C C 3 Dimethyl (4R,5R)-1,3,2 dioxathiolane-4,5 dicarboxylate 2,2 dioxide, [117470 90 3] C 6 8 8 S FW 240.19 441015 3C C 3 S Dimethyl (4S,5S)-1,3,2 dioxathiolane-4,5 dicarboxylate 2,2 dioxide [127854 46 0] C 6 8 8 S FW 240.19 3C S 374318 Dimethyl (R)-(+)-malate, [70681 41 3] C 6 10 5 FW 162.14 455040 3C ( )-Dimethyl D-tartrate, [13171 64 7] C 6 10 6 FW 178.14 242942 3C 42544 52 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(+)-Dimethyl L-tartrate, [608 68 4] C 6 10 6 FW 178.14 163457 3C Ethyl (R)-(+)-4 bromo-3 hydroxybutyrate [95310 94 4] C 6 11 Br 3 FW 211.05 542911 Br Ethyl (S)-( )-4 bromo-3 hydroxybutyrate [95537 36 3] C 6 11 Br 3 FW 211.05 479608 Br Ethyl (R)-(+)-4 chloro-3 hydroxybutyrate, 96% [90866 33 4] C 6 11 3 FW 166.60 460516 (+)-Methyl (S)-3 hydroxyvalerate, 98.0% (GC, sum of enantiomers) [42558 50 9] C 6 12 3 FW 132.16 56657 3C ( )-Isopropyl L-lactate, 97.0% (GC, sum of enantiomers) [63697 00 7] C 6 12 3 FW 132.16 69807 3C Ethyl (R)-( )-4 cyano-3 hydroxybutyrate, 95% [141942 85 0] C 7 11 3 FW 157.17 479772 C C 3 C 3 C 3 Dimethyl (R)-(+)-methylsuccinate, [22644 27 5] C 7 12 4 FW 160.17 3C C 3 C 3 Butyl (S)-( )-lactate, [34451 19 9] C 7 14 3 FW 146.18 420077 3C Isobutyl (R)-(+)-lactate, [61597 96 4] C 7 14 3 FW 146.18 316598 3C (+)-tert-butyl D-lactate, 99.0% (GC, sum of enantiomers) [68166 83 6] C 7 14 3 FW 146.18 69806 C 3 C 3 3C C 3 C 3 ( )-Butyl L-lactate, 97.0% (GC, sum of enantiomers) [34451 19 9] C 7 14 3 FW 146.18 69819 3C rganic Building Blocks Ethyl (S)-( )-4 chloro-3 hydroxybutyrate, 96% [86728 85 0] C 6 11 3 FW 166.60 460524 Ethyl (R)-( )-3 hydroxybutyrate, [24915 95 5] C 6 12 3 FW 132.16 347329 3C Ethyl (S)-3 hydroxybutyrate, [56816 01 4] C 6 12 3 FW 132.16 374709 3C ( )-Methyl (R)-3 hydroxyvalerate, 98.0% (GC, sum of enantiomers) [60793 22 8] C 6 12 3 FW 132.16 3C 382094 Methyl (R)-(+)-2,2 dimethyl-1,3 dioxolane-4 carboxylate, [52373 72 5] C 7 12 4 FW 160.17 345482 3C C 3 C 3 ( )-Methyl (S)-2,2 dimethyl-1,3 dioxolane-4 carboxylate, 96% [60456 21 5] C 7 12 4 FW 160.17 254606 3C Isobutyl (S)-2 chloropropionate, 99.0% (GC, sum of enantiomers) [83261 15 8] C 7 13 2 FW 164.63 51401 3C C 3 Ethyl (1R,2S)-cis-2 hydroxycyclopentanecarboxylate, 97.0% (GC) [61586 79 6] C 8 14 3 FW 158.19 55170 Ethyl (1S,2S)-trans-2 hydroxycyclopentanecarboxylate, 97.0% (GC, sum of enantiomers) [122331 03 7] C 8 14 3 FW 158.19 19713 Methyl (4S)-(+)-2,2 dimethyl- 1,3 dioxolane-4 acetate, [95422 24 5] C 8 14 4 FW 174.19 441856 3C 56655 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 53

rganic Building Blocks (+)-Diethyl L-tartrate, [87 91 2] C 8 14 6 FW 206.19 156841 3C ( )-Diethyl D-tartrate, [13811 71 7] C 8 14 6 FW 206.19 213969 3C C 3 C 3 tert-butyl (R)-2 hydroxybutyrate, [206996 51 2] C 8 16 3 FW 160.21 436984 3C ( )-tert-butyl (S)-2 hydroxybutyrate, [37787 90 9] C 8 16 3 FW 160.21 436976 3C C 3 C 3 C 3 Methyl (S)-(+)-3-(2,2 dimethyl- 1,3 dioxolan-4 yl)-cis-2 propenoate, 85% [81703 94 8] C 9 14 4 FW 186.21 347698 3C C 3 ( )-Dimethyl 2,3--isopropylidene- L-tartrate, [37031 29 1] C 9 14 6 3C FW 218.20 359068 3C (+)-Dimethyl 2,3--isopropylidene- D-tartrate, [37031 30 4] C 9 14 6 3C FW 218.20 384313 3C Ethyl (1R,2S)-cis-2 hydroxycyclohexanecarboxylate, 97.0% (GC) Benzyl (S)-( )-lactate, 90% [56777 24 3] C 10 12 3 FW 180.20 424846 3C Methyl L-3 phenyllactate, 97.0% (PLC) [13673 95 5] C 10 12 3 FW 180.20 68193 Methyl (2R,3S)-(+)-2,3 dihydroxy- 3 phenylpropionate, [122743 18 4] C 10 12 4 FW 196.20 482919 Methyl (2S,3R)-( )-2,3 dihydroxy- 3 phenylpropionate, [124649 67 8] C 10 12 4 FW 196.20 C 3 (+)-tert-butyl (S)-3 hydroxybutyrate, 96.0% (GC) [82578 45 8] C 8 16 3 FW 160.21 54953 3C Methyl (R)-( )-mandelate, [20698 91 3] C 9 10 3 FW 166.17 251550 Methyl (S)-(+)-mandelate, [21210 43 5] C 9 10 3 FW 166.17 251542 Methyl (S)-(+)-3-(2,2 dimethyl- 1,3 dioxolan-4 yl)-trans-2 propenoate, 93% [81703 93 7] C 9 14 4 FW 186.21 [61586 78 5] C 9 16 3 FW 172.22 17887 Ethyl (1S,2S)-trans-2 hydroxycyclohexanecarboxylate, 95.0% (GC) [29569 79 7] C 9 16 3 FW 172.22 89472 Ethyl (R)-( )-mandelate, [10606 72 1] C 10 12 3 FW 180.20 309982 Ethyl (S)-(+)-mandelate, [13704 09 1] C 10 12 3 FW 180.20 309974 C 3 482927 Methyl (R)-(+)-2-(4 hydroxyphenoxy)propionate, [96562 58 2] C 10 12 4 FW 196.20 472972 Ethyl (R)-cis-3-(2,2 dimethyl-1,3 dioxolan-4 yl)propenoate, 98.0% (GC, sum of enantiomers) [104321 63 3] C 10 16 4 FW 200.23 59431 3C C 3 Ethyl (R)-( )-3-(2,2 dimethyl-1,3 dioxolan-4 yl)-trans-2 propenoate, [104321 62 2] C 10 16 4 FW 200.23 382442 3C 3C 347965 54 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

Ethyl (S)-(+)-3-(2,2 dimethyl-1,3 dioxolan-4 yl)-2 propenoate,predominantly trans, [64520 58 7] C 10 16 4 FW 200.23 346810 3C C 3 Diisopropyl (S)-( )-malate, [83541 68 8] C 10 18 5 FW 218.25 454877 3C C 3 ( )-Diisopropyl D-tartrate, [62961 64 2] C 10 18 6 FW 234.25 227803 3C C 3 (+)-Diisopropyl L-tartrate, [2217 15 4] C 10 18 6 FW 234.25 229180 C 3 C 3 C 3 C 3 3C Methyl (R)-3 phenylbutyrate, 99.0% (GC, sum of enantiomers) [1472 07 7] C 11 14 2 FW 178.23 78275 (+)-Ethyl (R)-3 hydroxy-3 phenylpropionate, 99.0% (GC, sum of enantiomers) (+)-Methyl (R)-3-(1 methyl-2 oxocyclohexyl)propionate, [94089 47 1] C 11 18 3 FW 198.26 302945 Ethyl (S)-( )-2-(tert-butyldimethylsilyloxy)propionate, [106513 42 2] C 11 24 3 Si FW 232.39 424951 t-bu Si Methyl (S)-( )-4-(tert-butyldimethylsilyloxy)-2 hydroxybutanoate [307532 01 0] C 11 24 4 Si FW 248.39 648361 Si t-bu Ethyl (R)-( )-2 hydroxy-4 phenylbutyrate, [90315 82 5] C 12 16 3 FW 208.25 460826 (5R,6R)-Dimethyl 5,6 dimethoxy- 5,6 dimethyl-1,4 diox-2 ene- 2,3 dicarboxylate, C 12 18 8 FW 290.27 556947 3C 3C C 3 C 3 Ethyl (R)-nipecotate, L-tartrate, [167392 57 6] C 12 21 8 FW 307.30 472719 C 3 (1R)-( )-eomenthyl acetate, [146502 80 9] C 12 22 2 FW 198.30 420387 3C C 3 (1S)-(+)-eomenthyl acetate, [2552 91 2] C 12 22 2 FW 198.30 419990 3C (1R)-( )-Menthyl acetate, [2623 23 6] C 12 22 2 FW 198.30 441058 3C C 3 (1S)-(+)-Menthyl acetate, [5157 89 1] C 12 22 2 FW 198.30 3C C 3 C 3 C 3 C 3 rganic Building Blocks [72656 47 4] C 11 14 3 FW 194.23 56187 ( )-Ethyl (S)-3 hydroxy-3 phenylpropionate, 97.0% (GC, sum of enantiomers) [33401 74 0] C 11 14 3 FW 194.23 (2R,3R,5R,6R)-Dimethoxy-5,6 dimethyl-1,4 dioxane-2,3 dicarboxylic acid dimethyl ester, [181586 74 3] C 12 20 8 FW 292.28 556920 3C 3C C 3 441031 (+)-Ethyl (S)-2 hydroxy-4 cyclohexylbutyrate, 99.0% (GC, sum of enantiomers) C 12 22 3 FW 214.30 72437 ( )-Di-tert-butyl D-tartrate, C 3 56188 [117384 46 0] C 12 22 6 FW 262.30 420018 C 3 C 3 3C C 3 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 55

rganic Building Blocks (+)-Di-tert-butyl L-tartrate, [117384 45 9] C 12 22 6 FW 262.30 420026 3C C 3 tert-butyl (S)-2 hydroxyoctanoate, 97.0% (GC) C 12 24 3 FW 216.32 56067 3C C 3 C 3 (+)-Dimethyl 2,3--benzylidene-Dtartrate, 98.0% (GC, sum of enantiomers) [91326 83 9] C 13 14 6 FW 266.25 13476 C 3 (R)-( )-1 Phenylethyl 3,5 dinitrobenzoate, [3205 33 2] C 15 12 2 6 FW 316.27 461571 2 2 (S)-(+)-1 Phenylethyl 3,5 dinitrobenzoate, [3205 18 3] C 15 12 2 6 FW 316.27 461598 2 2 Benzyl (R)-( )-mandelate, [97415 09 3] C 15 14 3 FW 242.27 456497 ( )-Dibenzyl D-tartrate, 98.0% (PLC, sum of enantiomers) [4136 22 5] C 18 18 6 FW 330.33 95352 (1R,2S,5R)-(+)-5 Methyl-2-(1 methyl-1 phenylethyl)cyclohexyl chloroacetate, [71804 27 8] C 18 25 2 FW 308.84 341363 3C C 3 (R)-(+)-1,1,2 Triphenyl-1,2 ethanediol 2 acetate, [95061 47 5] C 22 20 3 FW 332.39 3C C 3 Methyl (R)-(+)-3 hydroxy-5 oxo- 1 cyclopentene-1 heptanoate, [41138 61 8] C 13 20 4 FW 240.30 463981 Methyl (S)-( )-3 hydroxy-5 oxo- 1 cyclopentene-1 heptanoate, [42038 75 5] C 13 20 4 FW 240.30 473073 ( )-Bis[(S)-1-(ethoxycarbonyl)ethyl] fumarate, Benzyl (S)-(+)-mandelate, [62173 99 3] C 15 14 3 FW 242.27 458295 Benzyl (R)-(+)-2 hydroxy-3 phenylpropionate, [7622 22 2] C 16 16 3 FW 256.30 461784 Benzyl (S)-( )-2 hydroxy-3 phenylpropionate, [7622 21 1] C 16 16 3 FW 256.30 376507 ( )-Dimenthyl fumarate, 95% [34675 24 6] C 24 40 4 FW 392.57 348910 3C 3C (1S)-(+)-Dimenthyl succinate, [96149 05 2] C 24 42 4 FW 394.59 306347 3C 3C 3C [111293 23 3] C 14 20 8 FW 316.30 374792 C 3 459879 (+)-Diisopropyl-, -bis(trimethylsilyl)-l-tartrate, [130678 42 1] C 16 34 6 Si 2 FW 378.61 C 3 3C Si C 3 C 3 3C C 3 3C Si C 3 C 3 (1R)-( )-Dimenthyl succinate, 3C [34212 59 4] C 24 42 4 FW 394.59 306355 3C 420131 56 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

ydrocarbons (S)-(+)-1 Bromo-2 methylbutane, [534 00 9] C 5 11 Br FW 151.04 250023 3C (S)-(+)-1 Iodo-2 methylbutane, [29394 58 9] C 5 11I FW 198.05 327131 3C Br I (+)-Cuparene, 99.0% (GC, sum of enantiomers) [16982 00 6] C 15 22 FW 202.34 3C (+)-α-pinene, [7785 70 8] C 10 16 FW 136.23 268070 ( )-α-pinene, [7785 26 4] C 10 16 FW 136.23 305715 ( )-β-pinene, [18172 67 3] C 10 16 FW 136.23 402753 3C 3C C 3 3C 3C 3C C 3 C 2 (+)-Camphene, 80% [5794 03 6] C 10 16 FW 136.23 C301 3C C2 C 3 ( )-Camphene, 75% (90% as camphene and fenchene) [5794 04 7] C 10 16 FW 136.23 310425 2C 3C (1R)-(+)-trans-Isolimonene, 95.0% (GC, sum of enantiomers) [5113 87 1] C 10 16 FW 136.23 2C C 3 rganic Building Blocks 28255 (S)-(+)-Citronellyl bromide, 95% [143615 81 0] C 10 19 Br FW 219.16 377716 3C (R)-( )-Citronellyl bromide, [10340 84 8] C 10 19 Br FW 219.16 377392 3C ( )-Menthyl chloride, [16052 42 9] C 10 19 FW 174.71 249246 3C C 3 (R)-( )-α-phellandrene, 95.0% (GC, sum of enantiomers) [4221 98 1] C 10 16 FW 136.23 3C C 3 Br Br C 3 (1S)-(+)-3 Carene, [498 15 7] C 10 16 FW 136.23 441619 (+)-2 Carene, [4497 92 1] C 10 16 FW 136.23 232386 3C 3C 3C 3C (1S,3R)-cis-4 Carene, 97.0% (GC, sum of enantiomers) [5208 49 1] C 10 16 FW 136.23 21987 3C (1S,3S)-trans-4 Carene, 85% (GC, sum of enantiomers) [5208 50 4] C 10 16 FW 136.23 21989 3C C 3 C 3 58923 (S)-( )-Limonene, 96% [5989 54 8] C 10 16 FW 136.23 218367 2C ( )-β-citronellene, 90% (GC, sum of enantiomers) [10281 56 8] C 10 18 FW 138.25 27477 (+)-Cyclosativene, [22469 52 9] C 15 24 FW 204.35 448559 3C C 2 C 3 C 3 3C 3C C 3 C 3 77429 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 57

rganic Building Blocks ( )-Isosativene, 97.0% (GC, sum of enantiomers) [24959 83 9] C 15 24 FW 204.35 59800 (+)-Valencene, 70% [4630 07 3] C 15 24 FW 204.35 75056 2C 3C C 3 C 3 C 2 ( )-β-chamigrene, ~90% (GC, sum of enantiomers) [18431 82 8] C 15 24 FW 204.35 22480 (3aS,6aS)-3,6-Diphenyl- 1,3a,4,6a-tetrahydropentalene, [940280 80 8] C 20 18 FW 258.36 C2 3C C 3 8 (3aR,6aR)-3,6-Diphenyl- 1,3a,4,6a-tetrahydropentalene, [947503 81 3] C 20 18 FW 258.36 698725 8 698733 Isocyanates/Isocyanides Methyl (S)-( )-2 isocyanato- 3 methylbutyrate, (S)-( )-α-methylbenzyl isocyanate, (R)-( )-1-(1 aphthyl)ethyl isocyanate, [30293 86 8] C 7 11 3 FW 157.17 3C C [14649 03 7] C 9 9 FW 147.17 C C 3 [42340 98 7] C 13 11 FW 197.23 3C C 429805 220566 220442 (S)-( )-α-methylbenzyl isocyanide, 96% [21872 32 2] C 9 9 FW 131.17 C Methyl (R)-(+)-2 isocyanato- 3 phenylpropionate, [361456 36 2] C 11 11 3 FW 205.21 C (S)-(+)-1-(1 aphthyl)ethyl isocyanate, [73671 79 1] C 13 11 FW 197.23 3C C 531324 (R)-(+)-α-Methylbenzyl isocyanate, 562653 Methyl (S)-( )-2 isocyanato- 3 phenylpropionate, 295957 [33375 06 3] C 9 9 FW 147.17 C [40203 94 9] C 11 11 3 FW 205.21 C 3 C 220574 409731 58 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

Ketones (R)-(+)-3 Methylcyclopentanone, [6672 30 6] C 6 10 FW 98.14 M39709 (R)-5 ydroxy-2 hexanone, 90% (GC, sum of enantiomers) [65709 73 1] C 6 12 2 FW 116.16 79199 3C (1R,5S)-(+)-cis-Bicyclo[3.2.0]hept- 2 en-6 one, 98.0% (GC, sum of enantiomers) [71155 05 0] C 7 8 FW 108.14 67519 ( )-(1S,5R)-cis-Bicyclo[3.2.0]hept- 2 en-6 one, 98.0% (GC, sum of enantiomers) [71155 04 9] C 7 8 FW 108.14 C 3 (1R)-(+)-opinone, [38651 65 9] C 9 14 FW 138.21 327956 3C (S)-(+)-2,3,7,7a-Tetrahydro-7amethyl-1-indene-1,5(6)-dione, [17553 86 5] C 10 12 2 FW 164.20 664073 (+)-3,9 Dibromocamphor, [10293 10 4] C 10 14 Br 2 FW 310.03 306428 (R)-( )-Carvone, [6485 40 1] C 10 14 FW 150.22 124931 (S)-(+)-Carvone, 96% 2C Br 3C 3C Br C 3 (1R)-( )-Camphorquinone, [10334 26 6] C 10 14 2 FW 166.22 276286 3C 3C (1S)-(+)-Camphorquinone, [2767 84 2] C 10 14 2 FW 166.22 272078 3C (3aS,7aS)-(+)-exahydro-3a-hydroxy-7a-methyl-1,5 indandione, [33879 04 8] C 10 14 3 FW 182.22 297933 3C (+)-3 Bromocamphor, 97.0% (GC, sum of enantiomers) [10293 06 8] C 10 15Br FW 231.13 16571 3C 3C Br rganic Building Blocks 69308 (R)-(+)-3 Methylcyclohexanone, [13368 65 5] C 7 12 FW 112.17 M38583 C 3 [2244 16 8] C 10 14 FW 150.22 435759 (1S)-( )-Verbenone, 94% [1196 01 6] C 10 14 FW 150.22 218251 C 3 2C C 3 C 3 3C 3C (R)-(+)-Pulegone, [89 82 7] C 10 16 FW 152.23 376388 (S)-( )-Pulegone, [3391 90 0] C 10 16 FW 152.23 3C C 3 C 3 3C C 3 328847 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 59

rganic Building Blocks ( )-Pulegone, 98.0% (GC, sum of enantiomers) [3391 90 0] C 10 16 FW 152.23 82579 (+)-Dihydrocarvone [5524 05 0] C 10 16 FW 152.23 37275 2C 3C (+)-Fenchone, 98.0% (GC, sum of enantiomers) [4695 62 9] C 10 16 FW 152.23 46210 (1R)-( )-Fenchone, [7787 20 4] C 10 16 FW 152.23 196436 α,β-thujone [76231 76 0] C 10 16 FW 152.23 3C 3C C 3 C 3 (1S)-( )-Camphor, [464 48 2] C 10 16 FW 152.23 279676 (S)-(+)-5-(1 ydroxy-1 methyl- ethyl)-2 methyl-2 cyclohexen- 1 one, [60593 11 5] C 10 16 2 FW 168.23 278807 3C 3C 3C C 3 (1R,2R,5R)-(+)-2 ydroxy-3 pinanone, [24047 72 1] C 10 16 2 FW 168.23 400416 3C (1S,2S,5S)-( )-2 ydroxy-3 pinanone, [1845 25 6] C 10 16 2 FW 168.23 380342 ( )-Menthone, 90% [14073 97 3] C 10 18 FW 154.25 3C C 3 3C C 3 (R)-( )-8a-Methyl-3,4,8,8a-tetrahydro-1,6(2,7)-naphthalenedione, 98.0% (GC, sum of enantiomers) [100348 93 4] C 11 14 2 FW 178.23 68169 3C (R)-( )-4,4a,5,6,7,8 exahydro-4amethyl-2(3)-naphthalenone, 98.0% (GC, sum of enantiomers) [63975 59 7] C 11 16 FW 164.24 52560 ( )-3-(Trifluoroacetyl)camphor, [207742 84 5] C 12 15 F 3 2 FW 248.24 298344 3C (+)-3-(Trifluoroacetyl)camphor, [51800 98 7] C 12 15F 3 2 FW 248.24 189006 (S)-(+)-Benzoin, 3C 3C CF3 CF 3 283118 ( )-α-thujone, 96.0% (GC) [546 80 5] C 10 16 FW 152.23 89231 (1R)-(+)-Camphor, [464 49 3] C 10 16 FW 152.23 3C 3C 3C 218235 (S)-(+)-3,4,8,8a-Tetrahydro-8amethyl-1,6(2,7)-naphthalenedione, [33878 99 8] C 11 14 2 FW 178.23 437026 3C [5928 67 6] C 14 12 2 FW 212.24 256250 (R)-( )-Benzoin, [5928 66 5] C 14 12 2 FW 212.24 459941 857300 60 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

3-(Perfluorobutyryl)-( )-camphor, [115224 00 5] C 14 15 F 7 2 FW 348.26 298336 3C F F CF3 F F 3-(Perfluorobutyryl)-(+)-camphor, 96% [51800 99 8] C 14 15F 7 2 FW 348.26 3C 3C F F CF3 F F Irone, 90% (GC) [79 69 6] C 14 22 FW 206.32 58220 3C 3C 5-[3,4-(Dimethoxy)phenyl]- 1,3 cyclohexanedione, [190064 28 9] C 14 16 4 FW 248.27 539902 3C 3C C 3 C 3 ( )-Isolongifolen-9 one, 99.5% (GC, sum of enantiomers) [26839 52 1] C 15 22 FW 218.33 58926 3C 3C 7 Acetyl-5,8 dihydroxy-4 isopropyl-1 methylbicyclo[4.3.0]nonane, [457949 49 4] C 15 26 3 FW 254.37 3C C 3 C 3 rganic Building Blocks 195936 (+)-ootkatone, 99.0% (GC) 541699 [4674 50 4] C 15 22 FW 218.33 74437 3C C2 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 61

Lactams/Lactones rganic Building Blocks (R)-4-(Trichloromethyl)-2 oxetanone, 99.0% (GC) [20710 33 2] C 4 3 3 2 FW 189.42 91292 3C (S)-( )-4 xo-2 azetidinecarboxylic acid, [16404 94 7] C 4 5 3 FW 115.09 473278 (R)-(+)-α-ydroxy-γ-butyrolactone, [56881 90 4] C 4 6 3 FW 102.09 444286 (S)-( )-α-ydroxy-γ-butyrolactone, [52079 23 9] C 4 6 3 FW 102.09 444235 (S)-β-ydroxy-γ-butyrolactone, 96% [7331 52 4] C 4 6 3 FW 102.09 422797 (S)-( )-α-amino-γ-butyrolactone hydrobromide, [15295 77 9] C 4 7 2 Br FW 182.02 471429 (R)-(+)-4 Methyl-4-(trichloromethyl)-2 oxetanone, 2 Br (S)-( )-4 Methyl-4-(trichloromethyl)-2 oxetanone, [93206 60 1] C 5 5 3 2 FW 203.45 340243 3C 3C (R)-γ-Valerolactone, 97.0% (GC) [58917 25 2] C 5 8 2 FW 100.12 43948 3C (1S)-(+)-2 Azabicyclo[2.2.1]hept- 5 en-3 one, [130931 83 8] C 6 7 FW 109.13 441287 (1R)-( )-2 Azabicyclo[2.2.1]hept- 5 en-3 one, [79200 56 9] C 6 7 FW 109.13 441279 (3S)-cis-3,6 Dimethyl-1,4 dioxane- 2,5 dione, [4511 42 6] C 6 8 4 FW 144.13 367044 3C C 3 (R)-5 exanolide, 95.0% (GC, sum of enantiomers) [43112 32 9] C 6 10 2 FW 114.14 94154 D-( )-Pantolactone, [599 04 2] C 6 10 3 3C 3C 3C (S)-(+)-Pantolactone, [5405 40 3] 3C C 6 10 3 3C FW 130.14 437328 L-( )-α-amino-ε-caprolactam hydrochloride, 97.0% (AT) [26081 07 2] C 6 12 2 FW 164.63 21612 (1S,5R)-2 xabicyclo[3.3.0]oct- 6 en-3 one, [43119 28 4] C 7 8 2 FW 124.14 448478 (1R,5S)-3 xabicyclo[3.3.0]oct- 6 en-2 one, 95.0% (GC) [128946 78 1] C 7 8 2 FW 124.14 75653 2 (R)-( )-γ-ethoxycarbonyl-γ-butyrolactone, 95% [33019 03 3] C 7 10 4 FW 158.15 346969 C 3 (3aR,4S,5R,6aS)-( )-exahydro- 5 hydroxy-4-(hydroxymethyl)-2cyclopenta[b]furan-2 one, [32233 40 2] C 8 12 4 FW 172.18 341576 [93239 42 0] C 5 5 3 2 FW 203.45 3C 3C FW 130.14 237817 340235 62 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(3aS,4R,5S,6aR)-(+)-exahydro- 5 hydroxy-4-(hydroxymethyl)-2cyclopenta[b]furan-2 one, [76704 05 7] C 8 12 4 FW 172.18 453218 (R)-α-Acryloyloxy-β,β-dimethyl-γbutyrolactone, 95% [102096 60 6] 3C C 9 12 4 3C FW 184.19 376361 C2 (+)-2,3 Cyclohexylidene-L-erythruronic acid, 96% [85281 85 2] C 10 14 5 FW 214.22 536245 Benzyl (S)-( )-4 oxo-2 azetidinecarboxylate, [72776 05 7] C 11 11 3 FW 205.21 468975 (+)-Corey lactone, 4 phenylbenzoate alcohol, [39265 57 1] C 21 20 5 FW 352.38 453226 ( )-Corey lactone, 4 phenylbenzoate alcohol, [31752 99 5] C 21 20 5 FW 352.38 249262 rganic Building Blocks (R)-2-tert-Butyl-6 methyl-1,3 dioxin-4 one, 99.0% (PLC, sum of enantiomers) [107289 20 3] C 9 14 3 FW 170.21 3C t-bu (R)-( )-Dihydro-5-(p-tolylsulfonyloxymethyl)-2(3)-furanone, [58879 33 7] C 12 14 5S FW 270.30 364541 S (S)-(+)-γ-Trityloxymethyl-γ-butyrolactone, [73968 62 4] C 24 22 3 FW 358.43 20264 (2R,6R)-2-tert-Butyl-6 methyl- 1,3 dioxan-4 one, 98.5% (GC, sum of enantiomers) [100017 18 3] C 9 16 3 FW 172.22 20260 3C (1R)-(+)-Camphanic acid, [67111 66 4] C 10 14 4 FW 198.22 382418 t-bu 3C C 3 C 3 (S)-(+)-Dihydro-5-(p-tolylsulfonyloxymethyl)-2(3)-furanone, [58879 34 8] C 12 14 5S FW 270.30 364568 S [3R(1 R,4R)]-(+)-4 Acetoxy-3-[1- (tert-butyldimethylsilyloxy)ethyl]- 2 azetidinone, [76855 69 1] C 13 25 4 Si FW 287.43 375845 3C 3C C 3 C 3 Si t-bu C 3 371521 (R)-( )-γ-trityloxymethyl-γ-butyrolactone, [78158 90 4] C 24 22 3 FW 358.43 438979 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 63

Polyamines (R)-(+)-1,2 Diaminopropane dihydrochloride, (1R,2R)-( )-1,2 Diaminocyclohexane, (1R,2R)-(+)-1,2 Diaminocyclohexane L-tartrate, rganic Building Blocks [19777 67 4] C 3 10 2 2 FW 147.05 412554 2 2 2 3C (S)-( )-1,2 Diaminopropane dihydrochloride, [19777 66 3] C 3 10 2 2 FW 147.05 412562 3C 2 2 2 [20439 47 8] C 6 14 2 FW 114.19 346721 (1S,2S)-(+)-1,2 Diaminocyclohexane, [21436 03 3] C 6 14 2 FW 114.19 346713 2 2 2 2 [39961 95 0] C 10 20 2 6 FW 264.28 416932 2 2 (1S,2S)-( )-1,2 Diaminocyclohexane D-tartrate, [67333 70 4] C 10 20 2 6 FW 264.28 416940 2 2 (R)-(+)-Propylenediamine dihydrochloride, 98.0% (TLC/AT) [19777 67 4] C 3 10 2 2 FW 147.05 82253 2 2 2 3C (R,R)-( )-, -Dimethyl-1,2 cyclohexanediamine, 97.0% (GC) [68737 65 5] C 8 18 2 FW 142.24 (1R,2R)-(+)-1,2 Diphenylethylenediamine, [35132 20 8] C 14 16 2 FW 212.29 2 2 (1S,2S)-trans-1,2 Cyclopentanediamine dihydrochloride, [477873 22 6] C 5 12 2 2 FW 173.08 670219 2 2 2 671274 (S,S)-(+)-, -Dimethyl-1,2 cyclohexanediamine, 97.0% (GC) [87583 89 9] C 8 18 2 FW 142.24 C 3 364010 (1S,2S)-( )-1,2 Diphenylethylenediamine, [29841 69 8] C 14 16 2 FW 212.29 2 2 (1R,2R)-trans-1,2 Cyclopentanediamine dihydrochloride, 669660 364002 C 5 12 2 2 FW 173.08 2 2 2 670324 64 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

Polyols (R)-( )-3 Chloro-1,2 propanediol, [57090 45 6] C 3 7 2 FW 110.54 540056 (S)-(+)-3 Chloro-1,2 propanediol, [60827 45 4] C 3 7 2 FW 110.54 540064 (2R,3R)-( )-2,3 Butanediol, [24347 58 8] C 4 10 2 FW 90.12 237639 3C (R)-(+)-1,2,4 Butanetriol, [70005 88 8] C 4 10 3 FW 106.12 309710 (S)-( )-1,2,4 Butanetriol, C 3 (S)-2 Methyl-1,4 butanediol, 97.0% (GC, sum of enantiomers) [70423 38 0] C 5 12 2 FW 104.15 53586 (1S-cis)-3 Bromo-3,5 cyclohexadiene-1,2 diol, 96% [130792 45 9] C 6 7Br 2 FW 191.02 489492 Br rganic Building Blocks (R)-( )-1,2 Propanediol, 96% [4254 14 2] C 3 8 2 FW 76.09 540242 (S)-(+)-1,2 Propanediol, 96% [4254 15 3] C 3 8 2 FW 76.09 540250 3C 3C (S)-3 Butene-1,2 diol, 97.0% (GC) [62214 39 5] C 4 8 2 FW 88.11 19159 (R)-( )-1,3 Butanediol, [6290 03 5] C 4 10 2 FW 90.12 237612 2C 3C [42890 76 6] C 4 10 3 FW 106.12 296678 (1R,2R)-(-)-trans-1,2 Cyclopentanediol, [930 46 1] C 5 10 2 FW 102.13 459259 (1S,2S)-(+)-trans-1,2 Cyclopentanediol, [63261 45 0] C 5 10 2 FW 102.13 459267 (R,R)-( )-2,4 Pentanediol, [42075 32 1] C 5 12 2 FW 104.15 3C (1S,2S)-trans-1,2 Cyclohexanediol, [57794 08 8] C 6 12 2 FW 116.16 421804 (1R,2R)-trans-1,2 Cyclohexanediol, [1072 86 2] C 6 12 2 FW 116.16 421790 (2S,5S)-2,5 exanediol, [34338 96 0] C 6 14 2 FW 118.17 396729 3C (2R,5R)-2,5 exanediol, 99.0% (GC, sum of enantiomers) C 3 (S)-(+)-1,3 Butanediol, [24621 61 2] C 4 10 2 FW 90.12 237620 3C (2S,3S)-(+)-2,3 Butanediol, [19132 06 0] C 4 10 2 FW 90.12 300349 3C 243175 (2S,4S)-(+)-Pentanediol, [72345 23 4] C 5 12 2 FW 104.15 267872 3C (R)-2 Methyl-1,4 butanediol, 98.0% (GC, sum of enantiomers) [22644 28 6] C 5 12 2 FW 104.15 [17299 07 9] C 6 14 2 FW 118.17 52792 3C (R)-( )-2 Methyl-2,4 pentanediol, [99210 90 9] C 6 14 2 FW 118.17 252840 C 3 3C 3C 04964 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 65

rganic Building Blocks (R)-(+)-3,3 Difluoro-1,2 heptanediol, 95% [158358 96 4] C 7 14 F 2 2 FW 168.18 477427 D-Pinitol, 95% [10284 63 6] C 7 14 6 FW 194.18 441252 F F (2R,6R)-2,6 eptanediol, 99.0% (GC, sum of enantiomers) [143170 07 4] C 7 16 2 FW 132.20 40617 (S)-(+)-1-(2 Chlorophenyl)- 1,2 ethanediol, 96% [133082 13 0] C 8 9 2 FW 172.61 494194 C 3 3C C 3 (R)-( )-1 Phenyl-1,2 ethanediol, [16355 00 3] C 8 10 2 FW 138.16 302163 (S)-(+)-1 Phenyl-1,2 ethanediol, [25779 13 9] C 8 10 2 FW 138.16 302155 (3R,6R)-3,6 ctanediol, 98.0% (GC, sum of enantiomers) [129619 37 0] C 8 18 2 FW 146.23 18717 3C (R)-(+)-1 Phenyl-1,3 propanediol, 99.0% (GC, sum of enantiomers) [103548 16 9] C 9 12 2 FW 152.19 78917 [3aS-(3aα,4α,5α,7aα)]-7 Bromo- 3a,4,5,7a-tetrahydro-2,2 dimethyl- 1,3 benzodioxole-4,5 diol, [130669 72 6] C 9 13 Br 4 FW 265.10 490350 Br [3aS-(3aα,4α,5α,7aα)]-3a,4,5,7a- Tetrahydro-2,2 dimethyl- 1,3 benzodioxole-4,5 diol, [130669 76 0] C 9 14 4 FW 186.21 490385 (R)-( )-1,3 onanediol, [121541 65 9] C 9 20 2 FW 160.25 538981 (C2)4C2 (1R,2S)-cis-1,2 Dihydro-1,2 naphthalenediol, 98.0% (GC) [51268 88 3] C 10 10 2 FW 162.19 37342 C 3 (1R,2R,3S,5R)-( )-Pinanediol, [22422 34 0] C 10 18 2 FW 170.25 287784 3C C 3 (1S,2S,3R,5S)-(+)-Pinanediol, [18680 27 8] C 10 18 2 FW 170.25 3C C 3 3C (R)-(+)-1,2 Decanediol, [87827 60 9] C 10 22 2 FW 174.28 483303 (C2)6C2 (S)-( )-1,2 Decanediol, [84276 14 2] C 10 22 2 FW 174.28 482218 (C2)6C2 [129705 30 2] C 10 22 2 FW 174.28 39277 3C (3S,6S)-2,7 Dimethyl-3,6 octanediol, 99.0% (GC, sum of enantiomers) (2R,3R)-( )-2 Benzyloxy- 1,3,4 butanetriol [84379 52 2] C 11 16 4 FW 212.24 13624 C 3 (R)-( )-1-(2 aphthyl)-1,2 ethanediol, [49801 14 1] C 12 12 2 FW 188.22 482862 (S)-(+)-1-(2 aphthyl)-1,2 ethanediol, [43210 74 8] C 12 12 2 FW 188.22 482870 (1S-cis)-3 Phenyl-3,5 cyclohexadiene-1,2 diol, [66008 24 0] C 12 12 2 FW 188.22 489638 282367 66 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(R,R)-( )-1 Phenylcyclohexane-cis- 1,2 diol, (1R,2R)-1,2 Dicyclohexyl- 1,2 ethanediol, 95% (S,S)-( )-1-(1 aphthyl)-2-(2 naphthyl)-1,2 ethanediol, [125132 75 4] C 12 16 2 FW 192.25 482935 (S,S)-(+)-1 Phenylcyclohexane-cis- 1,2 diol, [34281 90 8] C 12 16 2 FW 192.25 482943 [120850 92 2] C 14 26 2 FW 226.36 400149 (S)-( )-1,1 Diphenyl-1,2 propanediol, [46755 94 6] C 15 16 2 FW 228.29 364908 3C [229185 00 6] C 22 18 2 FW 314.38 482854 (S,S)-( )-1,2 Di(1 naphthyl)- 1,2 ethanediol, [229184 99 0] C 22 18 2 FW 314.38 482846 rganic Building Blocks (R)-(+)-1,2 Dodecanediol, [85514 84 7] C 12 26 2 FW 202.33 482234 (C2)8C2 (S)-( )-1,2 Dodecanediol, [85514 85 8] C 12 26 2 FW 202.33 482226 (C2)8C2 (S,S)-( )-ydrobenzoin, [2325 10 2] C 14 14 2 FW 214.26 256269 (S)-( )-1,1,2 Triphenyl-1,2 ethanediol, [108998 83 0] C 20 18 2 FW 290.36 367435 Sclareol [515 03 7] C 20 36 2 FW 308.50 357995 3C 3C C 3 (R,R)-(+)-1,2 Di(1 naphthyl)- 1,2 ethanediol, C2 [86436 19 3] C 30 20 2 2 FW 483.38 14662 (+)-1,6 Bis-(2 chlorophenyl)-1,6 diphenyl-2,4 hexadiyne-1,6 diol, 99.0% (PLC, sum of enantiomers) ( )-1,6 Bis(2 chlorophenyl)-1,6 diphenyl-2,4 hexadiyne-1,6 diol [96158 84 8] C 30 20 2 2 FW 483.38 (R,R)-(+)-ydrobenzoin, [52340 78 0] C 14 14 2 FW 214.26 [116204 39 8] C 22 18 2 FW 314.38 482900 C1662 256277 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 67

Protected Alcohols/Amines rganic Building Blocks (R)-(+)-4-(Chloromethyl)-2,2 dimethyl-1,3 dioxolane, [57044 24 3] C 6 11 2 FW 150.60 456136 (S)-( )-4-(Chloromethyl)-2,2 dimethyl-1,3 dioxolane, [60456 22 6] C 6 11 2 FW 150.60 3C C 3 3C C 3 ( )-Dihydrocarvyl acetate, 95% [20777 49 5] C 12 20 2 FW 196.29 194107 2C C 3 (R)-(+)-4 exyl-2,2 dimethyl-1,3 dioxane, [139008 44 9] C 12 24 2 FW 200.32 539678 (C2)4C2 (1R,2R)-( )--p-tosyl-1,2 cyclohexanediamine, C 13 20 2 2 S FW 268.38 677302 S 2 (1S,2S)-(+)--p-Tosyl-1,2 cyclohexanediamine, C 13 20 2 2 S FW 268.38 2 S C 3 456144 (R)-5 Acetoxy-1 chlorohexane, (S)-4 Benzyloxymethyl-2,2 dimethyl-1,3 dioxolane, 95.0% (GC, sum of enantiomers) 677310 (S)-( )-1,2 Propanediol di-p-tosylate, [154885 34 4] C 8 15 2 FW 178.66 531529 3C 3C (1R,2R)-trans---1,2 cyclohexanediamine, [146504 07 6] C 11 22 2 2 FW 214.30 670650 (1S,2S)-trans---1,2 cyclohexanediamine, [180683 64 1] C 11 22 2 2 FW 214.30 670766 ( )-Bornyl acetate, 95% 2 2 [16495 03 7] C 13 18 3 FW 222.28 59442 3C (R)-( )-2,2 Dimethyl-1,3 dioxolan- 4 ylmethyl p-toluenesulfonate, [23788 74 1] C 13 18 5 S FW 286.34 337412 3C S (S)-(+)-2,2 Dimethyl-1,3 dioxolan- 4 ylmethyl p-toluenesulfonate, [23735 43 5] C 13 18 5S FW 286.34 3C C 3 S C 3 3C [60434 71 1] C 17 20 6 S 2 FW 384.47 309656 S S C 3 ( )-2,3 Butanediyl di(p-toluenesulfonate), 3C [74839 83 1] C 18 22 6S 2 FW 398.49 310522 S S C 3 (1R,2R)-(+)-, -Di-p-tosyl- 1,2 cyclohexanediamine, [5655 61 8] C 12 20 2 FW 196.29 3C 337420 3C S S B55203 3C [143585 47 1] C 20 26 2 4 S 2 FW 422.56 482757 68 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(1S,2S)-( )-, -Di-p-tosyl- 1,2 cyclohexanediamine, (1R,2R)-( )--p-tosyl-1,2 diphenylethylenediamine, (1S,2S)-(+)--p-Tosyl-1,2 diphenylethylenediamine, 3C [212555 28 7] C 20 26 2 4S 2 FW 422.56 482765 S S Sulfonamides/Sulfinamides (R)-( )-p-toluenesulfinamide, [247089 85 6] C 7 9S FW 155.22 520497 3C S (S)-(+)-p-Toluenesulfinamide, [188447 91 8] C 7 9S FW 155.22 516899 3C S (1R)-trans-, -1,2 Cyclohexanediylbis(1,1,1 trifluoromethanesulfonamide), [122833 60 7] C 8 12F 6 2 4S 2 FW 378.31 433721 2 2 CF 3 S S CF 3 [144222 34 4] C 21 22 2 2 S FW 366.48 484334 2 S (S)-( )--[1-(ydroxymethyl)- 2 phenylethyl]-4 methylbenzenesulfonamide, [82495 70 3] C 16 19 3 S FW 305.39 470600 3C S (R,R)-(+)-, -Bis(α-methylbenzyl) sulfamide, [91410 68 3] C 16 20 2 2S FW 304.41 276081 C 3 S (S,S)-( )-, -Bis(α-methylbenzyl) sulfamide, [27304 75 2] C 16 20 2 2S FW 304.41 276073 C 3 S C 3 C 3 [167316 27 0] C 21 22 2 2 S FW 366.48 484342 2 S C 3 ( )-10 Dicyclohexylsulfamoyl-D-isoborneol, [99295 72 4] C 22 39 3S FW 397.61 297658 3C S (+)-,-Dicyclohexyl-(1R)-isoborneol-10 sulfonamide, [96303 88 7] C 22 39 3S FW 397.61 305790 3C C 3 S (1R,exo,exo)-3-[-(3,5 Dimethylphenyl)benzenesulfonamido]isoborneol, 98.5% (PLC, sum of enantiomers) rganic Building Blocks (1S)-10 Camphorsulfonamide, 96% [60933 63 3] C 10 17 3S FW 231.31 376612 2 S 3C (1R)-10 Camphorsulfonamide, (S)--( )-p-tolylsulfinyltryptamine, [288159 11 5] C 17 18 2S FW 298.40 588512 S C 3 [87420 26 6] C 24 31 3S FW 413.57 41390 3C 3C S [72597 34 3] C 10 17 3 S FW 231.31 3C S 2 375632 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 69

Sulfonates/Sulfinates (S)-(+)-2 Methylbutyl methanesulfonate, (1R)-( )-10 Camphorsulfonic acid, (1R,2S,5R)-( )-Menthyl (S)-p-toluenesulfinate, rganic Building Blocks [104418 40 8] C 6 14 3 S FW 166.24 303852 3C (2R,3R)-Butanediol bis(methanesulfonate), C 6 14 6 S 2 FW 246.30 681369 S 3C S S [(1R)-(endo,anti)]-(+)-3 Bromocamphor-8 sulfonic acid ammonium salt, [35963 20 3] C 10 16 4 S FW 232.30 282146 3C C 3 S 3 (1S)-(+)-10 Camphorsulfonic acid, [3144 16 9] C 10 16 4 S FW 232.30 C2107 3C S (1R)-( )-10 Camphorsulfonic acid ammonium salt [1517 82 4] C 17 26 2 S FW 294.45 278750 3C S 3C (1S,2R,5S)-(+)-Menthyl (R)-p-toluenesulfinate, [91796 57 5] C 17 26 2S FW 294.45 278742 3C S C 3 3C C 3 [14575 84 9] C 10 15 Br 4 S 3 FW 328.22 4 S 3C Br [82509 30 6] C 10 19 4S FW 249.33 3C S + 4 B60002 188360 (1S)-(+)-3 Bromocamphor-10 sulfonic acid hydrate, (S)-(+)-1 Methylpropyl 4 methylbenzenesulfonate, 95% [206860 46 0] C 10 15 Br 4 S x 2 FW 311.19 (Anh) 3C S C 3 Br x 2 [50896 54 3] C 11 16 3S FW 228.31 536229 3C S 374121 thers (R)-( )-1 Aminoethylphosphonic acid [60687 36 7] C 2 8 3 P FW 125.06 A6801 2 3C (S)-(+)-1 Aminoethylphosphonic acid, [66068 76 6] C 2 8 3 P FW 125.06 367559 2 3C P P (1S)-(+)-(1 Aminopropyl)phosphonic acid, [98048 99 8] C 3 10 3 P FW 139.09 471895 3C 2 P (R)-(+)-Propylene carbonate, [16606 55 6] C 4 6 3 FW 102.09 540013 C 3 (S)-( )-Propylene carbonate, [51260 39 0] C 4 6 3 FW 102.09 540005 (1R)-(+)-(1 Amino-2 methylpropyl) phosphonic acid, [66254 56 6] C 4 12 3P FW 153.12 471860 3C 2 C 3 P 70 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

(1S)-( )-(1 Amino-2 methylpropyl) phosphonic acid, (R)--(α-Methylbenzyl)hydroxylamine oxalate salt, 96% (1R,E)-(+)-Camphorquinone 3 oxime, [66254 55 5] C 4 12 3 P FW 153.12 471879 3C 2 P (S)-( )-2 ydroxy--methylsuccinimide, [104612 35 3] C 5 7 3 FW 129.11 370142 (R)-(+)-4-(Methoxymethyl)-1,3 dioxolan-2 one, [185836 34 4] C 5 8 4 FW 132.11 474010 (S)-( )-4-(Methoxymethyl)-1,3 dioxolan-2 one, [135682 18 7] C 5 8 4 FW 132.11 474002 (S)-( )-3 Acetylthio-2 methylpropanoic acid, [76497 39 7] C 6 10 3S FW 162.21 472522 3C (R)-(+)-Methyl p-tolyl sulfoxide, [1519 39 7] C 8 10 S FW 154.23 343609 3C (S)-( )-Methyl p-tolyl sulfoxide, [5056 07 5] C 8 10S FW 154.23 339997 3C S C 3 C 3 C 3 S S [118743 81 0] C 8 11 C 2 2 4 FW 227.21 690236 (S)--(α-Methylbenzyl)hydroxylamine oxalate salt, 96.0% [78798 33 1] C 8 11 C 2 2 4 FW 227.21 690333 (S)-( )-1,2 Epithiooctane, 90% [244221 84 9] C 8 16 S FW 144.28 477311 S C2(C2)4 [3aS-(3aα,4α,5β,7aα)]-5 Azido- 7 bromo-3a,4,5,7a-tetrahydro- 2,2 dimethyl-1,3 benzodioxol-4 ol, [171916 75 9] C 9 12Br 3 3 FW 290.11 493406 (1R)-( )-10 Camphorsulfonyl chloride, [39262 22 1] C 10 15 3S FW 250.74 301949 (1S)-(+)-10 Camphorsulfonyl chloride, [21286 54 4] C 10 15 3 S FW 250.74 219576 3 Br 3C 3C S 3C S (1S,E)-( )-Camphorquinone 3 oxime, [251645 83 7] C 10 15 2 FW 181.23 3C C 3 C 3 [31571 14 9] C 10 15 2 FW 181.23 273112 3C C 3 (1S)-( )-Camphorsulfonylimine, [60886 80 8] C 10 15 2 S FW 213.30 318361 3C (1R)-(+)-Camphorsulfonylimine, [107869 45 4] C 10 15 2S FW 213.30 319716 3C C 3 S S (1R)-Camphor oxime, 97.0% (GC, sum of enantiomers) [2792 42 9] C 10 17 FW 167.25 21335 3C 3C (R)-(+)-4-(2 Chlorophenyl)-2 hy- droxy-5,5 dimethyl- 1,3,2 dioxaphosphorinane 2 oxide, [98674 87 4] C 11 14 4 P FW 276.65 464392 P C 3 C 3 (S)-( )-4-(2 Chlorophenyl)-2 hy- droxy-5,5 dimethyl- 1,3,2 dioxaphosphorinane 2 oxide, [98674 86 3] C 11 14 4P FW 276.65 464406 P C 3 rganic Building Blocks 273120 Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 71

(4R)-2 ydroxy-5,5 dimethyl- 4 phenyl-1,3,2 dioxaphosphorinan 2 oxide, [98674 80 7] C 11 15 4 P FW 242.21 448427 P C 3 (+)-Chloromethyl isomenthyl ether, [144177 48 0] C 11 21 FW 204.74 453692 3C (+)-Chloromethyl menthyl ether, [103128 76 3] C 11 21 FW 204.74 349925 3C C 3 C 3 C 3 ( )-Chloromethyl menthyl ether, [26127 08 2] C 11 21 FW 204.74 349917 3C (R)-(+)--(1 Phenylethyl)maleimide, [6129 15 3] C 12 11 2 FW 201.22 461555 C 3 C 3 3C (S)-( )--(1 Phenylethyl)maleimide, [60925 76 0] C 12 11 2 FW 201.22 461563 3C (S)-( )-2 ydroxy-4-(2 methoxy- phenyl)-5,5 dimethyl- 1,3,2 dioxaphosphorinane 2 oxide, [98674 83 0] C 12 17 5 P FW 272.23 464384 3C C 3 P (R)-(+)-2 ydroxy-4-(2 methoxy- phenyl)-5,5 dimethyl- 1,3,2 dioxaphosphorinane 2 oxide, [98674 82 9] C 12 17 5 P FW 272.23 464376 (S)-( )-1,2 Epithiododecane [308103 61 9] C 12 24 S FW 200.38 477346 3C P C 3 C 3 S C2(C2)8 (R)-(+)-Aminoglutethimide, [55511 44 9] C 13 16 2 2 FW 232.28 545872 2 (S)-( )-Aminoglutethimide, [57288 03 6] C 13 16 2 2 FW 232.28 545864 C 3 (+)-Allylboronic acid pinanediol ester, C 13 21B 2 FW 220.12 694584 3C C 3 B (4S)-4-[(1R)-2 Azido-1-(benzyloxy) ethyl]-2,2 dimethyl-1,3 dioxolane C 14 19 3 3 FW 277.32 573213 3 3C (2R,5S)-5 Methyl-4,4 diphenyl- 1,3,2 dioxathiolane, [126577 49 9] C 15 14 3S FW 274.33 366714 2 C2 3C Ph Ph S (1R)-( )-opol benzyl ether, 95% [74851 17 5] C 18 24 FW 256.38 340375 3C 72 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

PTS ew Amphiphile for Metathesis and Cross-Coupling in Water Recently introduced by Professor Bruce Lipshutz of UC, Santa Barbara, polyoxyethanyl α-tocopheryl sebacate (PTS) is a nonionic amphiphile that is proving to be a versatile solubilizer for organic molecules in water. 1 Lipophilic substrates and catalysts can efficiently enter micelles formed by PTS in water, leading to cross-coupling reactions at room temperature without the need for a co-solvent. 2 R 1 R 2 R 1 Grubbs II cat. R 2 Grubbs II cat. Ar R ArX + RB() 2 Pd cat. R Ar X PTS Pd cat. X-Phos Ar X Pd cat. R Ar R R Ar 4 n PTS (n = ca. 13) Polyoxyethanyl α-tocopheryl sebacate, 15 wt. % in 2 698717 10 ml $47.50 References: (1) Sold under license from Zymes, LLC. (2) (a) Lipshutz, B.. et al. rg. Lett. 2008, 10, 1325. (b) Lipshutz, B.. et al. Adv. Synth. Catal. 2008, 350, 953. (c) Lipshutz, B.. et al. rg. Lett. 2008, 10, 1333. (d) Lipshutz, B..; Taft, B. R. rg. Lett. 2008, 10, 1329. (e) Lipshutz, B..; Ghorai, S. Aldrichimica Acta 2008, 41, in press. (f) Lipshutz, B.. et al. rg. Lett. 2008, 10, ASAP. sigma-aldrich.com

$ Risk and Safety Risk & Safety Phrases Risk Phrases IDICATI F PARTICULAR RISKS: R1: Explosive when dry 2: Risk of explosion by shock, friction, fire or other sources of ignition 3: Extreme risk of explosion by shock, friction, fire or other sources of ignition 4: Forms very sensitive explosive metallic compounds 5: eating may cause an explosion 6: Explosive with or without contact with air 7: May cause fire 8: Contact with combustible material may cause fire 9: Explosive when mixed with combustible material 10: Flammable 11: ighly flammable 12: Extremely flammable 14: Reacts violently with water 15: Contact with water liberates extremely flammable gases 16: Explosive when mixed with oxidizing substances 17: Spontaneously flammable in air 18: In use may form flammable/explosive vapor-air mixture 19: May form explosive peroxides 20: armful by inhalation 21: armful in contact with skin 22: armful if swallowed 23: Toxic by inhalation 24: Toxic in contact with skin 25: Toxic if swallowed 26: Very toxic by inhalation 27: Very toxic in contact with skin 28: Very toxic if swallowed 29: Contact with water liberates toxic gas 30: Can become highly flammable in use 31: Contact with acids liberates toxic gas 32: Contact with acids liberates very toxic gas 33: Danger of cumulative effects 34: Causes burns 35: Causes severe burns 36: Irritating to the eyes 37: Irritating to the respiratory system 38: Irritating to the skin 39: Danger of very serious irreversible effects 40: Limited evidence of a carcinogenic effect 41: Risk of serious damage to eyes 42: May cause sensitization by inhalation 43: May cause sensitization by skin contact 44: Risk of explosion if heated under confinement 45: May cause cancer 46: May cause heritable genetic damage 48: Danger of serious damage to health by prolonged exposure 49: May cause cancer by inhalation 50: Very toxic to aquatic organisms 51: Toxic to aquatic organisms 52: armful to aquatic organisms 53: May cause long-term adverse effects in the aquatic environment 54: Toxic to flora 55: Toxic to fauna 56: Toxic to soil organisms 57: Toxic to bees 58: May cause long-term adverse effects in the environment 59: Dangerous for the ozone layer 60: May impair fertility 61: May cause harm to the unborn child 62: Possible risk of impaired fertility 63: Possible risk of harm to the unborn child 64: May cause harm to breast-fed babies 65: armful: may cause lung damage if swallowed 66: Repeated exposure may cause skin dryness or cracking 67: Vapors may cause drowsiness and dizziness 68: Possible risk of irreversible effects CMBIATI F PARTICULAR RISKS: 14/15: Reacts violently with water, liberating extremely flammable gases 15/29: Contact with water liberates toxic, extremely flammable gas 20/21: armful by inhalation and in contact with skin 20/21/22: armful by inhalation, in contact with skin and if swallowed 20/22: armful by inhalation and if swallowed 21/22: armful in contact with skin and if swallowed 23/24: Toxic by inhalation and in contact with skin 23/24/25: Toxic by inhalation, in contact with skin and if swallowed 23/25: Toxic by inhalation and if swallowed 24/25: Toxic in contact with skin and if swallowed 26/27: Very toxic by inhalation and in contact with skin 26/27/28: Very toxic by inhalation, in contact with skin and if swallowed 26/28: Very toxic by inhalation and if swallowed 27/28: Very toxic in contact with skin and if swallowed 36/37: Irritating to eyes and respiratory system 36/37/38: Irritating to eyes, respiratory system and skin 36/38: Irritating to eyes and skin 37/38: Irritating to respiratory system and skin 39/23: Toxic: danger of very serious irreversible effects through inhalation 39/23/24: Toxic: danger of very serious irreversible effects through inhalation and in contact with skin 39/23/24/25: Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed 39/23/25: Toxic: danger of very serious irreversible effects through inhalation and if swallowed 39/24: Toxic: danger of very serious irreversible effects in contact with skin 39/24/25: Toxic: danger of very serious irreversible effects in contact with skin and if swallowed 39/25: Toxic: danger of very serious irreversible effects if swallowed 39/26: Very toxic: danger of very serious irreversible effects through inhalation 39/26/27: Very toxic: danger of very serious irreversible effects through inhalation and in contact with skin 39/26/27/28: Very toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed 39/26/28: Very toxic: danger of very serious irreversible effects through inhalation and if swallowed 39/27: Very toxic: danger of very serious irreversible effects in contact with skin 39/27/28: Very toxic: danger of very serious irreversible effects in contact with skin and if swallowed 39/28: Very toxic: danger of very serious irreversible effects if swallowed 42/43: May cause sensitization by inhalation and skin contact 48/20: armful: danger of serious damage to health by prolonged exposure through inhalation 48/20/21: armful: danger of serious damage to health by prolonged exposure through inhalation and in contact with skin 48/20/21/22: armful: danger of serious damage to health by prolonged exposure through inhalation, in contact with skin and if swallowed 48/20/22: armful: danger of serious damage to health by prolonged exposure through inhalation and if swallowed 48/21: armful: danger of serious damage to health by prolonged exposure in contact with skin 48/21/22: armful: danger of serious damage to health by prolonged exposure in contact with skin and if swallowed 48/22: armful: danger of serious damage to health by prolonged exposure if swallowed 48/23: Toxic: danger of serious damage to health by prolonged exposure through inhalation 48/23/24: Toxic: danger of serious damage to health by prolonged exposure through inhalation and in contact with skin 48/23/24/25: Toxic: danger of serious damage to health by prolonged exposure through inhalation, in contact with skin and if swallowed 48/23/25: Toxic: danger of serious damage to health by prolonged exposure through inhalation and if swallowed 48/24: Toxic: danger of serious damage to health by prolonged exposure in contact with skin 48/24/25: Toxic: danger of serious damage to health by prolonged exposure in contact with skin and if swallowed 74 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover), or visit sigma-aldrich.com/chemicalsynthesis.

$ 48/25: Toxic: danger of serious damage to health by prolonged exposure if swallowed 50/53: Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment 51/53: Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment 52/53: armful to aquatic organisms, may cause long-term adverse effects in the aquatic environment 68/20: armful: possible risk of irreversible effects through inhalation 68/20/21: armful: possible risk of irreversible effects through inhalation and in contact with skin 68/20/21/22: armful: possible risk of irreversible effects through inhalation, in contact with skin and if swallowed 68/20/22: armful: possible risk of irreversible effects through inhalation and if swallowed 68/22: armful: possible risk of irreversible effects if swallowed 68/21: armful: possible risk of irreversible effects in contact with skin 68/21/22: armful: possible risk of irreversible effects in contact with skin and if swallowed Safety Phrases IDICATI F SAFETY PRECAUTIS: S1: Keep locked up 2: Keep out of the reach of children 3: Keep in a cool place 4: Keep away from living quarters 5: Keep contents under... (appropriate liquid to be specified by the manufacturer) 6: Keep under... (inert gas to be specified by the manufacturer) 7: Keep container tightly closed 8: Keep container dry 9: Keep container in a well-ventilated place 12: Do not keep the container sealed 13: Keep away from food, drink and animal feeding stuffs 14: Keep away from... (incompatible materials to be indicated by the manufacturer) 15: Keep away from heat 16: Keep away from sources of ignition - o smoking 17: Keep away from combustible material 18: andle and open container with care 20: When using, do not eat or drink 21: When using, do not smoke 22: Do not breathe dust 23: Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) 24: Avoid contact with skin 25: Avoid contact with eyes 26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 27: Take off immediately all contaminated clothing 28: After contact with skin, wash immediately with plenty of... (to be specified by the manufacturer) 29: Do not empty into drains 30: ever add water to this product 33: Take precautionary measures against static discharges 35: This material and its container must be disposed of in a safe way 36: Wear suitable protective clothing 37: Wear suitable gloves 38: In case of insufficient ventilation, wear suitable respiratory equipment 39: Wear eye/face protection 40: To clean the floor and all objects contaminated by this material use... (to be specified by the manufacturer) 41: I n case of fire and/or explosion do not breathe fumes Pictograms Pictograms are based on widely accepted standards. G Explosive E xidizing J ighly Flammable or Extremely Flammable K Toxic or Very Toxic armful or Irritant 42: During fumigation/spraying wear suitable respiratory equipment (appropriate wording to be specified by the manufacturer) 43: In case of fire, use... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - ever use water) 45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 46: If swallowed, seek medical advice immediately and show this container or label 47: Keep at temperature not exceeding... ºC (to be specified by the manufacturer) 48: Keep wet with... (appropriate material to be specified by the manufacturer) 49: Keep only in the original container 50: Do not mix with... (to be specified by the manufacturer) 51: Use only in well-ventilated areas 52: ot recommended for interior use on large surface areas 53: Avoid exposure - obtain special instruction before use 56: Dispose of this material and its container to hazardous or special waste collection point 57: Use appropriate container to avoid environ mental contamination 59: Refer to manufacturer/supplier for information on recovery/ recycling 60: This material and/or its container must be disposed of as hazardous waste 61: Avoid release to the environment. Refer to special instructions/ safety data sheet 62: If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label 63: In case of accident by inhalation, remove casualty to fresh air and keep at rest 64: If swallowed, rinse mouth with water (only if the person is conscious) CMBIATI F SAFETY PRECAUTIS: 1/2: Keep locked up and out of the reach of children 3/7: Keep container tightly closed in a cool place 3/9/14: Keep in a cool well-ventilated place away from... (incompatible materials to be indicated by manufacturer) 3/9/14/49: Keep only in the original container in a cool well-ventilated place away from... (incompatible materials to be indicated by manufacturer) 3/9/49: Keep only in the original container in a cool well-ventilated place 3/14: Keep in a cool place away from... (incompatible materials to be indicated by the manufacturer) 7/8: Keep container tightly closed and dry 7/9: Keep container tightly closed and in a well-ventilated place 7/47: Keep container tightly closed and at a temperature not exceeding... ºC (to be specified by manufacturer) 20/21: When using, do not eat, drink or smoke 24/25: Avoid contact with skin and eyes 27/28: After contact with skin, take off immediately all contaminated clothing and wash immediately with plenty of... (to be specified by the manufacturer) 29/35: Do not empty into drains, dispose of this material and its container in a safe way 29/56: Do not empty into drains, dispose of this material and its container at hazardous or special waste-collection point 36/37: Wear suitable protective clothing and gloves 36/37/39: Wear suitable protective clothing, gloves and eye/face protection 36/39: Wear suitable protective clothing and eye/face protection 37/39: Wear suitable gloves and eye/face protection 47/49: Keep only in the original container at temperature not exceeding... ºC (to be specified by manufacturer) F T Xn F+ T+ L Xi C B Q R R MCorrosive I Biohazard Dangerous for the Environment Radioactive Risk and Safety Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 75

Risk & Safety Cat. o. Risk Safety 00031 Xi: 36/37/38... 26 00696 Xi: 36/37/38-43... 26-36/37 00791 Xn: 22-37/38-41... 26-39 00846... 23-24/25 00851 T: 23/24/25... 36/37/39-45 00873 Xn: 20/21/22-36/37/38... 26-36 02300 Xi: 37/38-41... 26-36 04855 T: 45-20/21-37/38-41-43-52/53-68... 53-26-36/37/39-45-61 05023 C: 22-34... 26-36/37/39-45 06368 Xn: 22-36/37/38... 26 06674 Xn: 22-37/38-41... 26-39 06782 Xn: 22... 07858 Xn: 22-36/37/38... 26 08011 F: 11... 16 08601 Xi: 37/38-41... 26-39 09222 C: 22-34... 26-36/37/39-45 09267 C: 22-34... 26-36/37/39-45 112577 Xi: 36/37/38... 26-36 115541 C: 21/22-34... 26-28-36/37/39-45 115568 C: 21/22-34... 26-28-36/37/39-45 11558 Xn: 22-36/37/38... 26 11584 Xn: 22-36/37/38... 26 12348 Xi: 36/37/38... 26-36 12351 Xi: 36/37/38... 26-36 124931 22... 36 132527 C: 22-34-37... 26-36/37/39-45 13597 Xi: 36/37/38... 26-36 13732... 22-24/25 139114 F,Xi: 11-43... 16-36/37 141879 T: 23/25... 36/37/39-45 147982 Xi: 36/37/38... 26-36 147990 Xi: 36/37/38... 26-36 15022 Xi: 36/37/38... 26-36 154210... 22-24/25 155268 Xi: 36/37/38... 26-36 155616 Xi: 36/37/38... 26-36 156868 Xi: 36/37/38... 26-36 163449 Xi: 36... 26-36 16571 Xi: 36/37/38... 26-36 16749 Xn: 22... 16995 Xi: 36/37/38... 23-26-36 17241 Xi: 36/37/38... 26-36 18069 C: 34... 26-28-36/37/39-45 18072 C: 34... 26-28-36/37/39-45 180807 Xi: 36/37/38... 26-36/37/39 18159 C: 34... 26-36/37/39-45 18165 C: 22-34... 26-36/37/39-45 18196 C: 34... 26-36/37/39-45 18241 F,C: 11-22-34... 26-36/37/39-45 18509 Xi: 36/38... 26 186511 Xi: 36/37/38... 26-36 186546 Xi: 36/37/38... 26-36 186708 Xi: 36... 26 187658... 23-24/25 188417... 23-24/25 189006 Xi: 36/37/38... 26-36 190047 Xn: 21/22... 24/25 190438 C: 34... 26-36/37/39-45 19159 Xi: 36/37/38... 26-36 19162 Xi: 36/37/38... 26 19163 Xi: 36/37/38... 26-36 192384 Xi: 36/37/38... 26-37/39 19377 F: 11... 16 194107... 23-24/25 19506 T: 25-37/38-41... 26-39-45 195936 Xi: 36/37/38... 26-36 196436 10... 23-24/25 19929 Xn: 22-36/37/38... 26 20260... 22-24/25 211346 Xi: 36/37/38... 26-36 Cat. o. Risk Safety 211354 Xi: 36/37/38... 26-36 218235... 23-24/25 218243... 23-24/25 218294 Xi: 36/37/38... 26 218359 Xi: 36/37/38... 26-36 218367 Xi,: 10-38-43-50/53... 24-37-60-61 218391 Xi: 36/37/38... 26-36 219576 C: 34... 26-36/37/39-45 21987 10... 23-24/25 21989 10... 23-24/25 220442 Xn: 36/37/38-42/43... 23-26-36/37 220566 Xn: 36/37/38-42... 23-26-36 220574 Xn: 36/37/38-42... 23-26-36 22110 Xi: 36/37/38... 26-36 224464 Xi: 37/38-41... 26-39 226173 C: 34... 26-36/37/39-45 227803... 23-24/25 230340 Xi: 10-36/37... 24 232386 10... 233935 Xi: 36/37/38... 26-36 235180 Xi: 37/38-41... 26-36 236691 Xi: 10-36/37-67... 9-13-24/25-26-46 237442 Xi: 36/37/38... 26-36 237450 Xi: 36/37/38... 26-36 237612 Xi: 36/37/38... 26-36 237620 Xi: 36/37/38... 26-36 237698 Xi: 10-36/37-67... 9-13-24-25-26-46 237744... 23-24/25 238856 C: 34... 23-26-36-45 238864 C: 34... 23-26-36-45 241407 F,C: 11-20/21/22-34... 16-26-36/37/39-45 241806... 23-24/25 242063 Xn: 22-36... 26 242071 Xi: 36/37/38... 26-36 243159 Xi: 36/37/38... 26-36/37 243167... 23-24/25 243175... 22-24/25 245305 T,: 23-34-51/53... 26-36/37/39-45-61 245526 C: 34... 26-36/37/39-45 247030 Xn: 10-36-48/22... 23-26-36 247065 Xi: 36/37/38... 26-36 247308 Xn: 10-20/21/22... 16-36 248509 Xn: 40-52... 23-24/25-36/37 248886 Xi: 36/37/38... 26-36 248967 Xi: 36/37/38... 26-36 248983 Xi: 36/37/38... 26-36 249246... 23-24/25 249262... 22-24/25 250023 Xi: 10-36/37/38... 26-36 25112 C: 34... 26-36/37/39-45 25113 C: 34... 26-36/37/39-45 251542... 22-24/25 251550... 22-24/25 252840 Xi: 36/38... 26-36 25301 Xi: 36/37/38... 26-36/37/39 253022... 22-24/25 253030... 22-24/25 254606... 23-24/25 254827... 22-24/25 256269... 22-24/25 256277... 22-24/25 256285 Xi: 36/37/38... 26-36 256293 Xi: 36/37/38... 26-36 256323 Xn: 22... 23-24/25 256331 Xn: 22... 23-24/25 263907... 22-24/25 267872... 22-24/25 268070 Xi: 10-36/37/38... 26-36 270148 10... 16 273112... 22-24/25 76 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

Cat. o. Risk Safety 273120 Xi: 22-43... 36/37 27477 10... 23-24/25 276065... 22-24/25 276073... 22-24/25 27618 10... 23-24/25 276286 Xn: 22-43... 36/37 277037 Xi: 36/37/38... 26-36 277061 Xi: 36/37/38... 26-36 277754 Xi: 10-36/37/38... 26-36 277762 Xi: 10-36/37... 24 278807 T+: 26/27/28... 22-36/37/39-45 279676 F,Xi: 11-36/37/38... 16-26 279870 Xn: 22... 23-36 279889 Xn: 22... 23-36 279897 Xi: 36/37/38... 26-36 279900 Xi: 36/37/38-43... 26-36 281573... 23-24/25 281581 Xi: 36/37/38... 26-36 281697 Xi: 36/37/38... 26-36 282146 C: 34... 26-36/37/39-45 28255 Xn: 22... 26-36 283118 T: 23/24/25-36/37/38-42/43... 23-26-36/37/39-45 284483 Xi: 36/37/38... 26-36/37 284491 C: 34... 26-36/37/39-45 284785 Xn: 22... 36/37 287784... 22-24/25 287792 Xi: 36/37/38... 26 28964 T: 25-36/37/38... 26-36/37/39-45 289981... 22-24/25 29177 C: 10-20/21/22-34-40... 26-36/37/39-45 292176 Xi: 36/37/38... 26-36 29438 T: 45-20/21-37/38-41-43-52/53-68... 53-26-36/37/39-45-61 295957 Xn: 36/37/38-42/43... 23-26-36/37 296643 F,C,: 11-20/22-35-50... 16-26-28-36/37/39-45-61 296651 F,C,: 11-20/22-35-50... 9-16-26-28- 36/37/39-45-61 296678... 23-24/25 296686 Xi: 36/37/38... 26 296708 Xn: 10-20/21/22-36... 16-26-27-36/37/39-45 296902 Xi: 36/37/38... 26-36 296910 Xi: 36/37/38... 26-36 297658 Xi: 36/37/38... 26-36 297682 C: 34... 26-36/37/39-45 298336 Xi: 36/37/38... 26-36 298344 Xi: 36/37/38... 26-36/37/39 300438 Xi: 36/37/38... 26-36 300446 Xi: 36/37/38... 26-36 300489 Xi: 36/37/38... 26-36 300500 Xi: 36/37/38... 26-36 300535 Xi: 36/37/38... 26-37/39 301469 Xi: 36/37/38... 26-36 30169 Xi: 36/37/38... 26 30192 C: 34... 26-36/37/39-45 301949 C: 34... 26-36/37/39-45 302147 Xn: 20/21/22-36/37/38... 26-36 302775 Xn: 20/21/22-36/37/38... 26-36 302945... 23-24/25 303461 Xi: 36/37/38... 26-36 303488 Xi: 36/37/38... 26-36 305251 T: 25... 36-45 305715 Xi,: 10-36/37/38-43-50... 26-36/37-61 305758 Xi: 36/37/38... 26-37/39 305766 Xi: 36/37/38... 26-36/37/39 305790 Xi: 36/37/38... 26-36 306355... 22-24/25 306428 Xi: 36/37/38... 26-36 306797 C: 21/22-35... 23-26-28-36/37/39-45 306800 C: 22-35... 23-26-28-36-45 307084 C: 22-34-37... 26-36/37/39-45 Cat. o. Risk Safety 309710 Xi: 36/37/38... 26-36 309753 Xi: 36/37/38... 26-36 310425 10... 16-29-33 310476 Xi: 36/37/38... 26-36 316520 Xi: 36/37/38... 26-36 316598 Xi: 36... 26 317322... 22-24/25 318035 Xi: 36/37/38... 26-36 318361 Xi: 36/37/38... 26-36 319716 Xi: 36/37/38... 26-36 323128 Xn: 22-36/37/38... 26-36 323144... 22-24/25 324612 Xi: 36/37/38... 26-37/39 324922 Xi: 36/37/38... 26-36 325058 Xi: 36/37/38... 26-36 325066 Xi: 36/37/38... 26-36 325090 Xi: 36/37/38... 26-36 327131 Xi: 10-36/37/38... 16-26-36 327247 Xi: 36/37/38... 26-36 328243 Xi: 36/37/38... 26-36 328413 Xn: 22-36/37/38... 26-36 328847 Xn: 22... 329142 Xi: 36/37/38... 26-36 329177 Xi: 36/37/38... 26-37/39 329487 Xi: 36/37/38... 26-36 329967 Xn: 22... 36 330515 Xi: 10-36/37/38... 16-26 330523 Xn: 10-20... 24/25 331074 Xi: 36/37/38... 26-36 331813 Xi: 36/37/38... 26-37/39 331848 Xi: 36/37/38... 26-37/39 331856 Xi: 36/37/38... 26-37/39 331872 Xi: 36/37/38... 26-37/39 331880 Xi: 36/37/38... 26-36 331899 Xi: 36/37/38... 26-36 334235 Xi: 36/37/38... 26-36/37/39 335975 F,Xi: 11-36-66-67... 16-26 33622 Xi: 36... 26-36 336505 C: 10-21/22-34... 26-36/37/39-45 336513 C: 10-34... 16-26-36/37/39-45 337412 Xi: 36/37/38... 26-36 337420 Xi: 36/37/38... 26-36 338125 Xn: 22-36/37/38-42/43... 23-36/37-45 338419 Xi: 36/37/38... 26-36 338710 F,Xi: 11-36-66-67... 9-16-26 339814 Xi: 36/37/38... 26-37/39 339822 Xi: 36/37/38... 26-37/39 340235 Xn: 20/21/22-36/37/38... 26-36 340243 Xi: 36/37/38... 26-36 340308 10... 340332 Xi: 36/37/38... 26-36/37/39 340367 Xn: 22-36/37/38... 26-37/39 340375 Xi: 36/37/38... 26-37/39 340499 Xn: 21-38... 26-36 341363 Xi: 36/37/38... 26-36 343544... 23-24/25 343609... 22-24/25 343641 Xi: 36/37/38... 26-36 345482... 23-24/25 345598 Xi: 36/37/38... 26-37/39 345628 Xi: 36/37/38... 26-37/39 345849 Xi: 36... 26 346217... 22-24/25 346713 C: 34... 26-36/37/39-45 346721 C: 34... 26-36/37/39-45 346810... 23-24/25 346969... 23-24/25 348368 Xi: 36/37/38... 26-37/39 348562 C: 34... 26-27-36/37/39-45 348902... 23-24/25 Risk & Safety Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 77

Risk & Safety Cat. o. Risk Safety 348910... 22-24/25 349607 Xi: 36/37/38... 26-36 349917 Xi: 36/37/38... 26-36 349925 Xi: 36/37/38... 26-36 358924 Xi: 36/37/38... 26-36 359068... 23-24/25 359939 Xi: 36/37/38... 26-36 361887 Xi: 36/37/38... 26-37/39 36323 Xi: 36/37/38... 26 363529 Xi: 36/37/38... 26-36 363537 Xi: 36/37/38... 26-36 363561... 23-24/25 364002 Xi: 36/37/38... 26-36 364010 Xi: 36/37/38... 26-36 364428 Xi: 38... 364541 Xi: 36/37/38... 26-37/39 364568 Xi: 36/37/38... 26-36 364886... 22-24/25 364908... 22-24/25 366358 Xi: 36/37/38... 26-36 366366 Xi: 36/37/38... 26-36 366714 Xi: 36/37/38... 26-37/39 366935 Xi: 36/37/38... 26-37/39 366943 Xi: 36/37/38... 26-37/39 367044 Xi: 36/37/38... 26-37/39 367435 Xi: 36/37/38... 26-36 367559 Xi: 36/37/38... 26-37/39 369675 C: 34... 26-27-36/37/39-45 370126 Xn: 20/21/22-36/37/38... 26-36 370142 Xi: 36/37/38... 26-36 37034 Xi: 36/37/38... 26-36 371416... 22-24/25 372315... 22-24/25 373753 Xi: 36/37/38... 26-36 374113 Xi: 36/37/38... 26-37/39 374121 C: 34... 26-36/37/39-45 374636 C: 34... 26-36/37/39-45 374709... 23-24/25 375845 Xi,: 36-43-51/53... 24-26-37-61 376361 Xi,: 36/37/38-51/53... 26-28-61 376388 Xn: 22... 23-24/25 376418... 22-24/25 376906... 22-24/25 377392 Xi: 36/37/38... 26-37/39 377716 Xi: 36/37/38... 26-37/39 378712 T: 23-34... 26-36/37/39-45 379093 Xi: 36/37/38... 26-36 380148... 22-24/25 380342... 22-24/25 382094... 23-24/25 382175... 22-24/25 382442... 23-24/25 382981 Xi: 36/37/38... 26-37/39 384313... 22-24/25 385514 C: 22-34... 26-36/37/39-45 388114 Xi: 36/37/38... 26-36 391190 Xi: 36/37/38... 26-36 391654 Xi: 36/37/38... 26-36 391662 Xi: 36/37/38... 26 391913 Xi: 36/37/38... 26-37/39 391921 Xi: 36/37/38... 26-37/39 392308 Xi: 36/37/38... 26-36 392480 T+: 26/27/28... 28-36/37-45 39277 Xi: 36/37/38... 26-36/37 393967 Xn: 20/21/22... 27-36/37/39-45 394009 C: 20/21/22-34... 26-36/37/39-45 396729 Xn: 22-36/37/38... 26-36 397164 F: 11-36/37/38... 16-26-36/37/39 397172 F,Xi: 11-36/37/38... 16-26 39867 Xn: 22-37/38-41... 26-39 Cat. o. Risk Safety 399701 Xn: 20/21/22... 27-36/37/39-45 399728 Xi: 36/37/38... 26-36 399736 Xi: 36/37/38... 26-36 400149... 22-24/25 401358 C: 20/21/22-34... 26-36-45 402753 Xn,: 10-20/21/22-36/37/38-43-51-65... 16-26-36/37-46-61-62 405086 Xi: 36/37/38... 26-36 405248 C: 20/21/22-34... 16-26-27-36/37/39-45 405256 C: 20/21/22-34... 16-26-27-36/37/39-45 40577 Xn: 22-36/38... 26 407453 T: 25... 36/37-45 40767 Xi: 36/37/38... 26-36 408697 Xn: 21-37/38-41... 26-36/37/39 409650 Xi: 36/37/38... 26-36 409731 Xn: 20/21/22-36/37/38... 26-36 410462 Xi: 36/37/38... 26-37/39 410918 Xi: 36/37/38... 26-36 411132 Xi: 36/37/38... 26-36 411140 Xi: 36/37/38... 26-36 412554 Xi: 36/37/38... 26-36 412562 Xi: 36/37/38... 26-36 412937 Xi: 10-36/37/38... 16-26-36/37/39 412945 Xi: 10-36/37/38... 16-26-36/37/39 41304 Xn: 22-37/38-41... 26-39 41390 Xi: 36/37/38... 26-36 415596 Xi: 36/37/38... 26-36 415618 Xi: 36/37/38... 26-36 41566 F,C: 11-22-34... 26-36/37/39-45 415715 Xi: 36/37/38... 26-38 415723 Xi: 36/37/38... 26-36 41609 Xn: 10-21/22-36/37/38-40... 26-36/37 416932 Xn: 20/21/22-36/37/38... 26-36 416940 Xn: 20/21/22... 36 419990 F,: 11-51/53... 16-61 420018... 22-24/25 420026... 22-24/25 420077 Xi: 36/37/38... 26-36 420131... 23-24/25 420247 F: 11... 420964 Xi: 36/37/38... 26-36 421588 Xi: 36/37/38... 26-36 421650 Xi: 36/37/38... 26-36 421693 Xi: 36/37/38... 26-36 421731 Xi: 36/37/38... 26-36 421804 Xi: 36/37-41... 26-39 422797 Xi: 36/37/38... 26-36 422800 Xi: 36/37/38... 26-36 422886 Xi: 10-36/37/38... 16-26-36 427470 Xi: 36/37/38... 26-36 429791 Xi: 36/37/38... 26-36 429805 Xn: 20/21/22-36/37/38... 23-26-36 430722 Xi: 36/37/38... 26-36 431737 Xi: 36/37/38... 26-36 432261 Xi: 36/37/38... 26-36 432628 Xi: 36/37/38... 26-36 433721 Xi: 36/37/38... 26-36 433810 Xi: 36/37/38... 26-36/37 434639 Xn: 22-36/37/38... 26-36 436976... 22-24/25 436984 Xi: 41... 26-39 437026... 22-24/25 438979... 22-24/25 439053 Xn: 22-36/37/38... 26-36/37/39 439061 Xn: 22-36/37/38... 26-36/37/39 43948 Xn: 22-36... 26-36 440329 Xi: 36/37/38... 26-36 440833 Xi: 36/37/38... 26-36 440841 Xi: 36/37/38... 26-36 441015... 22-24/25 441279 Xn: 22-41-43... 24-26-37/39 78 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

Cat. o. Risk Safety 441287 Xi: 36/37/38... 26-36 441570 Xi: 36/37/38... 26-36 441619 Xi,: 10-50/53... 36/37-60-61 444537 Xi: 36/37/38... 26-36 445347 Xi: 36/37/38... 26-36 445355 Xi: 36/37/38... 26-36 445584 Xi: 36/37/38... 26-36 445940 Xi: 36/37/38... 26-36 445959 Xi: 36/37/38... 26-36 446351 Xi: 36/38... 26-36 447056 C: 34... 26-36/37/39-45 448362... 22-24/25 448397 Xi: 36/37/38... 26-36 448427 Xi: 36/37/38... 26-36 448443 Xi: 36/37/38... 26-36 448532 Xi: 36/37/38... 26-36 448540 Xi: 36/37/38... 26-36 452823 Xi: 36/37/38... 26-36/37 453382 Xn: 20/21/22... 26-27-28-36/39 453692 Xi: 36/37/38... 26-36 453714 C: 34... 26-36/37/39-45 454680 F,Xi: 11-19-36/37/38... 16-26 454699 F,Xi: 11-19-36/37/38... 16-26 454877 Xi: 36/37/38... 26-36 45510 T: 23/24/25-62-63... 36/37-45 455172 T: 25-36/37/38... 26-45 456136 Xi: 10-41... 16-26-36 456144 Xi: 10-41... 16-26-36 456152 Xi: 36/37/38... 26-36 458538 Xi: 36/37/38... 26-36 458546 Xi: 36/37/38... 26-36 458554 Xn: 20/21/22... 26-36 458562 Xn: 20/21/22... 36 458570 Xn: 20/21/22... 36 460028 Xi: 36/37/38... 26-36 460508 Xi: 36/37/38... 26-36 460516 Xi: 41... 26-36 460524 Xi: 41... 26-36 460826... 23-24/25 461385 C: 34... 26-36/37/39-45 461393 C: 34... 26-36/37/39-45 461407... 23-24/25 461415... 23-24/25 461423 Xi: 36/37/38... 26-36 461431 Xi: 36/37/38... 26-36 461458 Xi: 36/37/38... 26-36 461466 Xi: 36/37/38... 26-36 461474 Xi: 36/37/38... 26-36 461482 Xi: 36/37/38... 26-36 461490 Xi: 36/37/38... 26-36 461504 Xi: 36/37/38... 26-36 461520 Xi: 36/37/38... 26 461555 Xi: 36/37/38... 26-36 461563 Xi: 36/37/38... 26-36 461601 Xi: 36/37/38... 26-36 461628 Xi: 36/37/38... 26-36 461636 Xi: 36/37/38... 26-36 461644 Xi: 36/37/38... 26-36 461652 Xi: 36/37/38... 26-36 461660 Xi: 36/37/38... 26-36 461679 Xi: 36/37/38... 26-36 461687 Xi: 36/37/38... 26-36 462039 C: 10-34... 16-26-27-36/37/39-45 462101 C: 20/21/22-34... 26-27-28-36/37/39-45 462403 Xi: 36/37/38... 26-36 462624 Xi: 10-36/37/38... 26-36 462632 Xi: 10-36/37/38... 26-36 463396 Xi: 36/37/38... 26-36 464007 F,T+: 11-26/27/28-36/38... 16-26-36/37/39-45 464376 Xi: 36/37/38... 26-36 Cat. o. Risk Safety 464384 Xi: 36/37/38... 26-36 464392 Xi: 36/37/38... 26-36 464406 Xi: 36/37/38... 26-36 464821 T+: 10-26/28-36/37/38-40-41-43... 16-24-26-36/37/39-45 465054 Xi: 36/37/38... 26-36 465062 : 51/53... 61 468347 C: 20/21/22-34... 26-27-28-36/37/39-45 469424 Xi: 36/37/38... 26-36 469432 Xi: 36/37/38... 26-36 469653 T: 23/24/25-36/37/38-41... 22-26-36/37/39-45 469688 Xn: 20/21/22-36/37/38... 26-37/39 469734 Xn: 20/21/22-36/37/38... 26-37/39 469742 Xn: 20/21/22... 36 470600 Xi: 36/37/38... 26-37/39 471429... 22-24/25 471631 Xi: 36/37/38... 26-36 471860 Xi: 36/37/38... 26-36 471879 Xi: 36/37/38... 26-36 471895 Xi: 36/37/38... 26-36 471909 Xn: 22-36/37/38-50/53... 26-60-61 472522 C: 34... 26-36/37/39-45 472719 Xi: 36... 26-36 472891 Xi: 36/37/38... 26-36 472905 Xi: 36/37/38... 26-36 472972 Xi: 41-52/53... 26-39-61 473367 Xi: 36/37/38... 26-36 473391 Xi: 36/37/38... 26-36 473405 Xi: 36/37/38... 26-36 473758 C: 34... 26-27-36/37/39-45 473960 C: 34... 26-36/37/39-45 474533 Xi: 41... 26-39 474789 T: 45-60-21/22-23-36/37/38-68... 53-26-36/37/39-45 475548 Xi: 36/37/38... 26-36 476986 Xi: 36/37/38... 26-36 477087 F,Xn: 11-22-36/37/38... 16-26 477109 Xi: 10-36/37/38... 26-36/37/39 477141 Xi: 36/37/38... 26-36 477168 Xi: 36/37/38... 26-36 477176 Xi: 36/37/38... 26-36 477184 Xi: 36/37/38... 26-36 477281 Xi: 37/38-41... 26-36 477346 Xi: 36/37/38... 26-36 479160 Xi: 36/37/38... 26 479179... 22-24/25 479284 C: 34... 26-36/37/39-45 479292 C: 22-34... 26-36/37/39-45 479772 Xi: 36/37/38... 26-36 479926 Xi: 36/37/38... 26-36 480819 T: 45-60-21/22-23-37/38-41-68... 53-26-36/37/39-45 482641 T: 25... 36/37/39-45 482757 Xi: 36/37/38... 26-36 482846 Xi: 36/37/38... 26-36 482854 Xi: 36/37/38... 26-36 482900 Xi: 36/37/38... 26-36 483796 Xi: 36/37/38... 26-36/37 484334 Xi: 36/37/38... 26-36 484342 Xi: 36/37/38... 26-36 487244 Xi: 36/37/38... 26-36 493740 Xn: 22-52/53... 61 494186 Xi: 36/37/38... 26-36 494577 C: 22-34... 26-36/37/39-45 49554 Xn: 22-52/53... 61 496057 Xi: 36/37/38... 26-36 49671 F,Xn: 11-22-36/37/38... 16-26 499587 Xi: 36/37/38... 26-36 50047 Xi: 36/37/38... 26-36 50048 Xi: 5-36/37/38... 26-36 50282 C: 22-34... 26-36/37/39-45 510343 Xi: 36/37/38... 26-36 510505 Xn: 22-37/38-41... 26-39 Risk & Safety Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 79

Risk & Safety Cat. o. Risk Safety 51241 Xn: 20/21/22-36/37/38... 26-36/37 51401 Xn: 22-36/37/38... 26 51432 C: 22-34... 26-36/37/39-45 516015 Xi: 36/37/38... 26-36 516058 Xi: 36/37/38... 26-36 516120 Xi: 36/37/38... 26-36 516376 Xi: 36/37/38... 26-36 51989 Xi: 36-43... 26-36/37 520497 Xi: 36/37/38... 26-36 52057 Xi: 36/37/38... 26 522880 Xi: 36/37/38... 26-36 522902 F,Xi: 11-36/37/38... 16-26-36 523720 Xi: 36/37/38... 26-36 52560... 23-24/25 527890 C: 22-34... 26-36/37/39-45 52792 Xn: 22-36/37/38... 26-36 52927 Xi: 36/37/38... 26 531324 Xn: 20/21/22-36/37/38... 23-26-27-28 531529 Xn: 22-36/37/38-40... 26-36 532150 Xi: 36/37/38... 26-36 532169 Xi: 36/37/38-50-53... 26-36 532355 F,T: 20/21/22-34-40... 16-26-27-36/37/39-45 532363 F,T: 20/21/22-34-40... 16-26-27-36/37/39-45 532509 C: 34... 26-27-36-45 532517 Xi: 36/37/38... 26-36 532525 Xi: 36/37/38... 26-36 532657 Xi: 36/37/38... 26-36 532665 Xi: 36/37/38... 26-36 532673 Xn: 20/21/22... 26-36 532908 Xi: 36/37/38... 26-36 533106 Xi: 36/37/38... 26-36 534552 Xi: 36/37/38... 26-36 534560 Xi: 36/37/38... 26-36 534579 Xi: 36/37/38... 26-36 534587 Xi: 36/37/38... 26-36 536229 C: 34... 26-27-36/37/39 536598 Xi: 36/37/38... 26-36 536601 Xi: 36/37/38... 26-36 536628 Xi: 36/37/38... 26-36 536644 Xi: 36/37/38... 26-36 537306 Xi: 36/37/38... 26-36 538167 Xi: 36/37/38... 26-36 538183 Xi: 36/37/38... 26-36 539007 Xi: 36/37/38... 26-36 540005 Xi: 36/37/38... 26-36 540013 Xi: 36/37/38... 26-36 540021 F+,T: 45-20/21/22... 53-45 540048 F+,T: 12-25... 45 540056 T: 25-41... 26-28-39-45 540064 T: 21-25-41... 26-28-39-45 540072 T: 45-10-23/24/25-34-43... 53-45 540080 T: 45-10-23/24/25-34-43... 53-45 540099 T: 45-21-36... 53-45 540102 T: 45-20/21-36/38... 53-26-36/37-45 540110 T,: 45-41-43-51/53-68... 53-26-36/37/39-45-61 540129 T,: 45-41-43-51/53-68... 53-45-61 540781 Xi: 36/37/38... 26-36 540803 Xi: 36/37/38... 26-36 542776 Xi,: 43-50... 24-35-37-61 543039 Xi: 36/37/38... 26-36 545481 Xi: 36/37/38... 26-36 545740 T: 25... 26-36/37/39-45 545864 Xi: 36/37/38... 26-36 545872 Xi: 36/37/38... 26-36 546704 Xn: 22... 546720 Xi: 10-36/37/38... 26-36 548979 Xi: 36/37/38... 26-36 54920 Xi: 36/37/38... 26-36 54925 Xi: 36/37/38... 26-36 549460 Xi: 36/37/38... 26-36 Cat. o. Risk Safety 549479 Xi: 36/37/38... 26-36 549487 Xi: 36/37/38... 26-36 549495 Xi: 36/37/38... 26-36 549525 Xi: 36/37/38... 26-36 549533 Xi: 36/37/38... 26-36 551015 Xi: 36/37/38... 26-36 551074 Xi: 36/37/38... 26-36 551082 Xi: 36/37/38... 26-36 551090 Xi: 36/37/38... 26-36 551147 Xi: 36/37/38... 26-36 551155 Xi: 36/37/38... 26-36 551953 Xi: 36/37/38... 26-36 551961 Xi: 36/37/38... 26-36 551988 Xi: 36/37/38... 26-36 551996 Xi: 36/37/38... 26-36 552526 Xi: 36/37/38... 26-37/39 552550 Xi: 36/37/38... 26-36 552569 Xi: 36/37/38... 26-36 554464 Xi: 36/37/38... 26-36 554472 Xi: 36/37/38... 26-36 554510 Xi: 36/37/38... 26-36 55452 Xi: 36/37/38... 26-36 554529 Xi: 36/37/38... 26-36 554553 Xi: 36/37/38... 26-36 554561 Xi: 36/37/38... 26-36 554618 Xi: 36/37/38... 26-36 554626 Xi: 36/37/38... 26-36 554634 Xi: 36/37/38... 26-36 554642 Xi: 36/37/38... 26-36 55673... 22-24/25 557900 Xn: 20/21/22-36/37/38... 26-35-36 557951... 24/25 557978... 24/25 558028 10... 558036 10... 558044 10... 558052 Xi: 10-37... 24/25 558060 10... 558079 Xi: 10-37... 24/25 559032 C: 34... 23-26-36/37/39-45 56193 Xi: 36/37/38... 26-36 562653 Xi: 10-36/37/38... 26-36/37/39 56308 Xi: 36/37/38... 26 563382 Xi: 36/37/38-43... 26-36/37 56437 Xi: 36/37/38... 26 570516 Xi: 36/37/38... 26-36 570524 Xi: 36/37/38... 26-36 570532 Xi: 36/37/38... 26-36 570540 Xi: 36/37/38... 26-36 570559 Xi: 36/37/38... 26-36 570842 Xn: 22... 36/37 570877 Xi: 36/37/38... 26-36 571326 Xi: 36/37/38... 26-36 573213 Xn: 22... 36 573337 Xi: 36/37/38... 26-36 586250 Xi: 36/37/38... 26-36 58923 10... 591017 Xn: 22-37/38-41-42/43... 26-36 591246 Xn: 36/37/38-42/43... 26-36 591343 Xi: 36/37/38... 26-36 591564 Xn: 22-37/38-41-42/43... 26-36 591653 Xn: 36-42/43... 26-36 591734 T: 25-36/37/38-42/43... 26-36/37/39-45 591785 T: 25-41-42/43... 22-26-36/37/39-45 591882 Xn: 22-37/38-41-42/43... 26-36 592005 Xn: 22-37/38-41-42/43... 26-36 62139 C: 34... 26-36/37/39-45 63207 Xi: 37/38-41... 26-39 634786 T: 25-37/38-41... 26-39-45 634794 Xn: 22-41... 26 80 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

Cat. o. Risk Safety 637505 Xn: 22-36/37/38... 26 637513 Xn: 22-36/37/38... 26 642002 Xn: 22... 642118 Xn: 22... 644064 Xn: 22-41-44... 26-36/37/39 647233 Xn: 22-36/37/38-43... 26-36/37/39 647241 Xi: 36/37/38... 26-36 647446 Xi: 36/37/38... 26-36 647462 Xn,: 22-37/38-41-50/53... 26-36/37/39-60-61 647470 Xn,: 22-37/38-41-50/53... 26-36/37/39-60-61 647497 Xi: 36/37/38... 26-36 649147 F,C: 11-22-34... 26-36/37/39-45 649961 Xi: 36/37/38... 26-36 649988 Xi: 36/37/38... 26-36 650838 Xn: 22-36/37/38... 26 650846 Xn: 22-36/37/38... 26-36 650919 Xi: 36/37/38... 26-36 651559 Xi: 36/37/38... 26-36 654639 Xi: 36/37/38... 26-36 654647 Xi: 36/37/38... 26-36 654655 T: 25-36/37/38... 26-45 654663 T: 25-36/37/38... 26-36-45 655236 Xn: 10-22-36/37/38... 16-26-36 656356 Xi: 36/37/38... 26-36 656364 Xi: 36/37/38... 26-36 656704 Xn: 10-22-37/38-41... 26-39 656712 Xn: 10-22-37/38-41... 26-36/39 656747 Xn: 22-36/37/38... 26-36 656755 Xn,: 22-36/37/38-50... 26-60-61 660051 Xn: 22-36/37/38... 26-36 660078 Xn: 22-36/37/38... 26-36 660108 C: 22-34... 26-36/37/39-45 660116 C: 22-34... 26-36/37/39-45 660205 T: 25... 45 663336 Xi: 36/37/38... 26-36 663344 Xi: 36/37/38... 26-36 664073 Xn: 22-36/37/38-43... 26-36/37 665061 Xn: 22... 665088 Xn: 22-36/37/38... 26 665614 F,Xn: 11-22-36/37/38... 26-36 665797 F+: 12... 3 666130 Xi: 37/38-41-43... 26-36/37/39 666297 Xn: 22-37/38-41... 26-39 666718 Xi: 36/37/38... 26 667005 F+: 12... 3 668427 F,C: 11-22-34... 16-26-36/37/39-45 668516 F,C: 11-22-34... 16-26-36/37/39-45 668796 C,: 34-51/53... 26-36/37/39-45-61 668818 Xi,: 36/37/38-51/53... 26-61 669660 C: 22-34... 26-36/37/39-45 669768 Xn: 22... 669865 Xn: 22... 669989 Xn: 22... 670057 Xn: 22-36/37/38... 26 670170 Xn: 22-36/37/38... 26 670219 Xi: 36/37/38... 26 670286 Xi: 36/37/38... 26 670324 Xi: 36/37/38... 26 670650 C: 34... 26-36/37/39-45 670766 C: 34... 26-36/37/39-45 670863 Xn,: 22-50... 61 670987 Xn,: 22-50... 61 671126 Xn: 22... 671223 Xn: 22... 671274 C: 22-34... 26-36/37/39-45 671312 Xn,: 22-50... 61 671436 Xn,: 22-50... 61 671606 Xi: 41... 26-39 671649 C: 21/22-34... 26-36/37/39-45 671711 Xi: 41... 26-39 Cat. o. Risk Safety 67176 Xi: 36/37/38... 26 672033 Xn: 22... 672297 Xi: 36/37/38... 26 672408 Xi: 36/37/38... 26 674761 Xi: 37/38-41... 26-39 67519 Xn: 22-37/38-41... 26-39 675377 Xn: 22... 676322 Xi: 36... 26 676691 Xi: 36... 26 676705 Xi: 36... 26 677302 Xn: 22-36/37/38... 677310 Xn: 22-36/37/38... 679097 F,C: 11-22-34... 26-36/37/39-45 679380 Xi: 36/37/38... 26 679399 Xn: 22-36/37/38... 26-36/37 679410 Xn: 22-36/37/38... 26 67948 F,Xn: 11-20/21/22-36/37/38... 16-26-36 680087 F,Xn,: 11-22-36/37/38-50... 16-26-61 681202 Xn: 22-36... 26 681229 : 50... 61 681369 Xn: 22... 681709 Xn: 22-37/38-41... 26-39 68249 Xi: 36/37/38... 26-36 684325 Xn: 22... 685291 T: 25... 45 685828 Xn: 22-38-41... 26-39 685836 Xn: 22-38-41... 26-39 685844 Xn: 22-36/37/38... 26 685852 Xn: 22-36/37/38... 26 686271 Xn: 20/21/22-36/37/38... 26 686298 Xn: 22-41-52/53... 26-39-61 686301 Xn: 20/21/22-36/37/38... 26 686336 Xn: 20/21/22-36/37/38... 26 687278 T: 25-37/38-41... 26-36/37/39-45 687324 Xi: 36/37/38... 26 687332 Xi: 36/37/38... 26-36/37 687340 Xi: 36/37/38... 26-36/37 687367 Xi: 36/37/38... 26 687588 T,: 25-37/38-41-50... 26-39-45-61 688525 T,: 25-50... 45-61 689017 C: 34... 26-36/37/39-45 69167 Xn: 22... 69308 Xn: 22-37/38-41... 26-39 694584 Xi: 36/37/38... 26-36 696404 Xn: 22-36... 26 697680 Xi: 36-43... 26-36/37 69784 Xi: 36/38... 26 69796 Xi: 10-37-41... 24-26-39 69819 Xi: 36/37/38... 26-36 698660 Xi: 36-43... 26-36/37 702498 Xn: 20/21/22-41... 26-36/37-39 70940 Xi: 36/37/38... 26-36 70942 Xi: 36/37/38... 26-36 73525 Xi: 36-43... 26-36/37 75914 Xn: 22... 76477 Xn: 10-21/22-36/37/38-40... 26-36/37 77301 Xi: 36/37/38... 26-36 77429 10... 77913 10... 77914 C: 22-34... 26-36/37/39-45 78803 Xi: 36/37/38... 26-36 78972 Xi: 36/37/38... 26-36 78974 Xi: 36/37/38... 26-36 82253 Xi: 36/37/38... 26-36 82579 Xn: 22... 83903 Xi: 36/37/38... 26-36 857300 F,Xn: 11-22-36/37/38... 16-26 87437 Xi: 36/37/38... 26-36 88808 10... 89095 Xi: 36... 26 Risk & Safety Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 81

Risk & Safety Cat. o. Risk Safety 89231 Xn: 22... 91292 Xi: 36/37/38... 26 91724 C: 34... 26-36/37/39-45 91936 F,C: 11-20/21/22-35... 26-36/37/39-45 93786 C,: 22-34-50... 26-36/37/39-45-61 95889 C: 34... 26-36/37/39-45 A154 Xi: 36/37/38... 26-36 A6801 Xi: 36/37/38... 26-36 A70704 Xn: 22-36/37/38... 26 A70909 Xn: 42/43... 22-36/37 A76206 C: 34... 26-36/37/39-45 A83407 Xn: 10-20... 24/25 B60002 Xi: 36/37/38... 26-37/39 C003 T: 23/24/25... 22-36/37/39-45 C2107 C: 34... 26-36/37/39-45 C301 F: 11... 16-33 Cat. o. Risk Safety C409 Xn: 22... E34102 Xi: 10-37-41... 24-26-39 G2410 Xi: 36/37/38... 26-36 I13901 F,Xi: 11-38... M1125 Xi: 37/38-41... 26-39 M2004... 22-24/25 M2780 Xi: 37/38-41... 26-39 M3000 Xi: 36/37/38... 26-36 M38583 10... 16-27-36/37/39 M3933 F,T: 11-23/24/25-39/23/24/25... 7-16-36/37-45 M39709 10... 16-29-33 3386 Xi: 36/37/38... 26 1631... 22-24/25 T109 Xi: 36/37/38... 26 V104 Xn: 20/21/22... 36 82 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

ew Aldrich andbook! ver 6,000 Innovative ew Products Request your copy of the new 2009 2010 Aldrich andbook set today. 2009-2010 Aldrich andbook 10,000 chemical structures 8,500 updated literature citations Extensive chemical & physical data Labware Catalog Innovative new products Improved product images ew technical information index To request your complimentary Aldrich andbook set, visit sigma-aldrich.com/aldrichcat sigma-aldrich.com