Chiral Building Blocks

Transcript

1 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

2 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 Teutonia Ave. Milwaukee, WI 53209, USA To Place rders Telephone FAX Vol. 9 o (USA) (USA) Customer & Technical Services Customer Inquiries Technical Service SAFC Custom Synthesis Flavors & Fragrances International our Emergency Web Site sigma-aldrich.com aldrich@sial.com Subscriptions To request your FREE subscription to ChemFiles, please contact us by: Phone: (USA) Mail: Attn: Marketing Communications Aldrich Chemical Co., Inc. Sigma-Aldrich Corporation P.. Box 355 Milwaukee, WI 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 ) is a publication of Aldrich Chemical Co., Inc. Aldrich is a member of the Sigma-Aldrich Group Sigma-Aldrich Co. 2

3 eterocyclic Building Blocks Furans (S)-(+)-3 ydroxytetrahydrofuran, [ ] C FW (R)-( )-3 ydroxytetrahydrofuran, [ ] C FW (S)-(+)-5 xo-2 tetrahydrofurancarboxylic acid, [ ] C FW (R)-Tetrahydrofuran-2 carbonitrile, 98.0% (GC, sum of enantiomers) [ ] C 5 7 FW C (R)-Tetrahydrofurfuryl alcohol, 98.0% (GC, sum of enantiomers) [ ] C FW (S)-(+)-Tetrahydrofurfurylamine, [ ] C 5 11 FW eterocyclic Building Blocks (R)-(+)-Tetrahydro-3 furylamine p-toluenesulfonate salt, 99.0% (T) [ ] C 4 9 C S FW S 3 C 3 (S)-(+)-Dihydro-5-(hydroxymethyl)- 2(3)-furanone, 95% [ ] C FW (R)-( )-Tetrahydrofurfurylamine, [ ] C 5 11 FW (R)-(+)-5 ydroxymethyl-2(5)- furanone, 97.0% (PLC, sum of enantiomers) [ ] C FW (R)-( )-Dihydro-5-(hydroxymethyl)- 2(3)-furanone, [ ] C FW (R)-(+)-Tetrahydro-2 furoic acid, (S)-( )-1-(2 Furyl)ethanol, 99.0% (GC, sum of enantiomers) [ ] C FW Benzyl (S)-( )-tetrahydro-5 oxo- 3 furanylcarbamate, (S)-( )-5 ydroxymethyl-2(5)- furanone, [ ] C FW [ ] C FW Cbz [ ] C FW (R)-( )-5 xo-2 tetrahydrofurancarboxylic acid, [ ] C FW (S)-( )-Tetrahydro-2 furoic acid, [ ] C FW (S)-( )-Tetrahydrofuran-2 carboxamide, [3aR(3aα,4α,5β,6aα)]-( )-5- (Benzoyloxy)hexahydro-2 oxo-2cyclopenta[b]furan-4 carboxaldehyde, 95% [ ] C FW C FW Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 3

4 (3aR)-(+)-Sclareolide, (+)-oe-lactol dimer, ( )-oe-lactol dimer, eterocyclic Building Blocks [ ] C FW ( )-Ambroxide, [ ] C FW C 3C C 3 3C 3C C 3 [ ] C FW C 3C C 3 3C C 3 3C [ ] C FW C 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.

5 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, [ ] C FW (S)-(+)-2 Indolinemethanol, [ ] C 9 11 FW (S)-(+)-α-ydroxy-1,3 dioxo-2 isoindolinebutyric acid, C FW (3S)-(+)-3-(1 Methyl-1-indol-3 yl)- 1 butanol, C FW C FW (3R)-( )-3-(methyl-1-indol-3 yl)- 3 phenylpropionic acid, C FW eterocyclic Building Blocks [ ] C FW Methyl (3R)-( )-3-(1 methylindol- 3 yl)butanoate, C FW C Methyl (3S)-(+)-3-(methyl-1-indol- 3 yl)-3 phenylpropionate, (3S)-( )-3-(1 Methyl-1-indol-3 yl) butanenitrile, C FW C FW C (3S)-(+)-3-(1 Methylindol-3 yl)- 3 phenylpropionitrile, C FW ( )-7 ctylindolactam V, ~90% (3S)-(+)-3-(1 Methyl-1-indol-3 yl)- 1 butyraldehyde, [ ] C FW C C 3 C [ ] C FW C 3C C 3 C Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 5

6 Isoquinolines eterocyclic Building Blocks (S)-1,2,3,4 Tetrahydro-3 isoquinolinecarboxylic acid, 97.0% (T) [ ] C FW (S)-( )-1,2,3,4 Tetrahydro-3 isoquinolinemethanol, [ ] C FW (S)-( )-6,7 Dimethoxy-1,2,3,4 tetrahydroisoquinoline-3 carboxylic acid hydrochloride, [ ] C FW C 3C (S)-( )--tert-butyl-1,2,3,4 tetrahydro-3 isoquinolinecarboxamide, [ ] C FW C 3 [3S-(3α,4aβ,8aβ)]--(tert-Butyl) decahydro-3 isoquinolinecarboxamide, [ ] C FW Benzyl (S)-( )-1,2,3,4 tetrahydro- 3 isoquinolinecarboxylate p-toluenesulfonic acid salt, [ ] C C S FW C S (R)-(+)-1-(4 Methoxybenzyl)- 1,2,3,4,5,6,7,8 octahydroisoquinoline, [ ] C FW (S)-(+)-2-(Benzyloxycarbonyl)- 1,2,3,4 tetrahydro-3 isoquinolinecarboxylic acid, [ ] C FW (S)-( )-1,2,3,4 Tetrahydro-α,α-diphenyl-3 isoquinolinemethanol, [ ] C FW 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, [ ] C FW [ ] C FW [ ] C FW Cbz (S)-4-3 morpholineacetic acid, 97.5% (PLC) [ ] C FW (2R,3S)-( )---6 oxo- 2,3 diphenylmorpholine, [ ] C FW (2R,3S)-( )--Z-6 oxo-2,3 diphenylmorpholine, [ ] C FW Cbz (S)-( )---5 benzyl-2 oxomorpholine, [ ] C FW sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

7 xazoles/xazolines Methyl (S)-(+)-4,5 dihydro-2 phenyl-4 oxazolecarboxylate, 96% [ ] C FW C (4S,5S)-( )-2 Methyl-5 phenyl- 2 oxazoline-4 methanol, [ ] C FW C 3 Methyl (4S,5S)-dihydro-5 methyl- 2 phenyl-4 oxazolecarboxylate, [ ] C FW C 3C (4S,5S)-( )-4,5 Dihydro-4 methoxymethyl-2 methyl-5 phenyloxazole, [ ] C FW C Ethyl (2S)-(+)-2-[4-(6 chlorobenzoxazol-2 yloxy)phenoxy] propanoate, 95% [ ] C FW eterocyclic Building Blocks Piperazines (R)-3 Methyl-2 ketopiperazine, 99.0% (GC) C FW (S)-(+)-2 Methylpiperazine, [ ] C FW (S)-3-tert-Butyl-2,5 piperazinedione, 99.0% (C) [ ] C FW t-bu (S)-3 Methyl-2 ketopiperazine, 99.0% (GC) [ ] C FW (R)-( )-3 Isopropyl-2,5 piperazinedione, [ ] C FW C (R)-1-3 methylpiperazine, [ ] C FW (R)-2 Piperazinecarboxylic acid dihydrochloride, 98.0% (T) [ ] C FW (S)-3 Isopropyl-2,5 piperazinedione, 99.0% (PLC, sum of enantiomers) [ ] C FW C 3 (S)-1-3 methylpiperazine, 98.0% (GC) [ ] C FW C 3 (R)-( )-2 Methylpiperazine, [ ] C FW Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 7

8 eterocyclic Building Blocks (2S-cis)-( )-5 Benzyl-3,6 dioxo- 2 piperazineacetic acid, [ ] C FW Piperidines (R)-(+)-3 ydroxypiperidine hydrochloride, (R)-( )-α-[[(4 Ethyl-2,3 dioxo-1 piperazinyl)carbonyl]amino]benzeneacetic acid, [ ] C FW (R)-( )-3 Piperidinecarboxylic acid, C 3 (R)-( )-α-[[(4 Ethyl-2,3 dioxo-1 piperazinyl)carbonyl]amino]- 4 hydroxybenzeneacetic acid, [ ] C FW (R)-1-3 hydroxypiperidine, 95% [ ] C 5 11 FW [ ] C FW [ ] C FW (S)-3 ydroxypiperidine hydrochloride, 98.0% (AT) [ ] C 5 11 FW (R)-( )-3 Aminopiperidine dihydrochloride, [ ] C FW (S)-(+)-3 Aminopiperidine dihydrochloride, 96% [ ] C FW (S)-(+)-3 Piperidinecarboxylic acid, [ ] C FW (S)-(+)-2 Methylpiperidine, [ ] C 6 13 FW (R)-2 Piperidineethanol hydrochloride, 98.0% (GC) [ ] C 7 15 FW C 3 (S)-1-3 hydroxypiperidine, [ ] C FW (R)-( )-3 Amino-1 -piperidine, 98.0% (TLC) [ ] C FW (S)-(+)-3 Amino-1 -piperidine, 98.0% (TLC) [ ] C FW (S)-6 xo-2 piperidinecarboxylic acid, 95.0% (PLC) [ ] C FW (S)-2 Piperidineethanol hydrochloride, 98.0% (GC) [ ] C 7 15 FW (S)-3-(-amino)piperidine, 98.0% (TLC) [ ] C FW sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

9 (S)-1-4 oxopiperidine- 2 carboxylic acid, 95% (R)-( )-1 Benzyl-3 hydroxypiperidine, (R)-(+)-1 Cbz-2 piperidinecarboxylic acid, C FW (R)-1--4-oxopiperidine-2- carboxylic acid, C FW (S)-1 -piperidine-3 carboxylic acid, [ ] C FW [ ] C FW (S)-1-2 piperidineacetic acid, 99.0% (PLC) [ ] C FW (R)-1-2 piperidineacetic acid, 99.0% (PLC) [ ] C FW [ ] C FW D-(+)-Vesamicol hydrochloride [ ] C FW V104 Cbz ( )-Lobeline hydrochloride, [ ] C FW Ph eterocyclic Building Blocks (S)-(+)--()-2 methylpiperidine, [ ] C FW Ethyl (S)---piperidine-3- carboxylate, 95% [ ] C FW (R)-( )-2 Piperidino-1,1,2 triphenylethanol, [ ] C FW (S)-1 Benzyl-3 hydroxypiperidine, 97.0% (GC) (S)-( )-1 Cbz-2 piperidinecarboxylic acid, (S)-(+)-2 Piperidino-1,1,2 triphenylethanol, [ ] C FW [ ] C FW Cbz [ ] C FW Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 9

10 Pyrans eterocyclic Building Blocks (S)-6 Chloromethyl-5,6 dihydropyran-2 one, 98.0% (GC) [ ] C FW (3aS,4R,6S,7aS)-Tetrahydro- 4 hydroxymethyl-6 methoxy-4furo[3,2-c]pyran-2(3)-one, [ ] C FW 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, [ ] C FW C C 3 C 3 (S)-( )-6 ydroxy-2,5,7,8 tetramethylchroman-2 carboxylic acid, [ ] C FW C C 3 C 3 (+)-Catechin hydrate, 96.0% (PLC, sum of enantiomers) [ ] C x 2 FW (Anh) ,3,4,6 Tetra--benzyl-α-D-glucopyranosyl trichloroacetimidate [ ] C FW R R R = C 2 R C 3 R x2 [ ] C FW C T8050 Pyridines (R)-α-Methyl-2 pyridinemethanol, 98.0% (GC) [ ] C 7 9 FW (S)-α-Methyl-2 pyridinemethanol [ ] C 7 9 FW (R)-(+)-α-Methyl-4 pyridinemethanol, [ ] C 7 9 FW C (S)-( )-α-methyl-4 pyridinemethanol, [ ] C 7 9 FW C (S)---1,2,3,6 tetrahydro-2 pyridinecarboxylic acid, 98.0% (PLC) [ ] C FW (3S,5R,8aS)-(+)-exahydro-3 phe- nyl-5-oxazolo[3,2-a]pyridine- 5 carbonitrile, [ ] C FW C (3R,5S,8aR)-( )-exahydro-3 phe- nyl-5-oxazolo[3,2-a]pyridine- 5 carbonitrile, [ ] C FW C [2S-(2α,3β,8aβ)]-(+)-exahydro-3- (hydroxymethyl)-8a-methyl-2 phe- nyl-5-oxazolo[3,2-a]pyridin- 5 one, [ ] C FW C 3 10 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

11 Pyrrolidines (R)-(+)-4 ydroxy-2 pyrrolidinone, [ ] C FW (S)-( )-4 ydroxy-2 pyrrolidinone, [ ] C FW (S)-(+)-3 Fluoropyrrolidine hydrochloride, [ ] C 4 8 F FW (R)-( )-3 Fluoropyrrolidine hydrochloride, [ ] C 4 9 F FW F F (S)-( )-3 Aminopyrrolidine, [ ] C FW (R)-(+)-3 Aminopyrrolidine, [ ] C FW (R)-( )-2-(Trifluoromethyl) pyrrolidine, [ ] C 5 8 F 3 FW (S)-(+)-2-(Trifluoromethyl) pyrrolidine, [ ] C 5 8 F 3 FW (R)-( )-5-(ydroxymethyl)- 2 pyrrolidinone, 2 2 CF3 CF3 (S)-(+)-2 Pyrrolidinemethanol, [ ] C 5 11 FW (R)-( )-2 Pyrrolidinemethanol, [ ] C 5 11 FW (R)-( )-1 Methyl-3 pyrrolidinol [ ] C 5 11 FW (S)-(+)-1 Methyl-3 pyrrolidinol, 95% [ ] C 5 11 FW C 3 (S)-(+)-2-(Aminomethyl)pyrrolidine, eterocyclic Building Blocks (S)-3 Pyrrolidinol, 97.0% (GC, sum of enantiomers) [ ] C 4 9 FW (R)-3 Pyrrolidinol, [ ] C FW (S)-5-(ydroxymethyl)- 2 pyrrolidinone, [ ] C FW [ ] C FW cis-3 Azabicyclo[3.1.0]hexane- 2 carboxylic acid, 2 [ ] C FW [ ] C 4 9 FW (R)-( )-3 Pyrrolidinol hydrochloride, [ ] C 4 9 FW (R)-( )-2 Methylpyrrolidine [ ] C 5 11 FW (S)-(+)-2 Methylpyrrolidine, 90% [ ] C 5 11 FW Methyl (S)-(+)-2 pyrrolidone- 5 carboxylate, [ ] C FW C Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 11

12 eterocyclic Building Blocks -[(2S)-2 Pyrrolidinylmethyl]-trifluoromethanesulfonamide, 98.5% (T) [ ] C 6 11 F S FW (2R,5R)-( )-trans-2,5 Dimethylpyrrolidine, 97.0% (GC) [ ] C 6 13 FW (R)-(+)-3-(Dimethylamino) pyrrolidine, 95% S CF3 3C C 3 (S)-( )-2-(Methoxymethyl)- 1 pyrrolidinecarboxaldehyde, [ ] C FW (S)-( )-2 Aminomethyl-1 ethylpyrrolidine, 96% [ ] C FW (R)-(+)-2-Aminomethyl-1- ethylpyrrolidine, 90% 2 8 (S)-(+)---3 pyrrolidinol, [ ] C FW (R)-(+)-1-3 aminopyrrolidine, [ ] C FW (S)-( )-1-3 aminopyrrolidine, 95% 2 [ ] C FW C [ ] C FW C 3 2 [ ] C FW (S)-( )-3-(Dimethylamino) pyrrolidine, [ ] C FW (R)-(+)-1 Amino-2-(methoxymethyl)pyrrolidine, 96% [ ] C FW (S)-( )-1 Amino-2-(methoxymethyl)pyrrolidine, 95% [ ] C FW C 2 2 (S)-( )--(Trifluoroacetyl) pyrrolidine-2 carbonyl chloride solution [ ] C 7 7 F 3 2 FW F3C (S,S)-2,2 -Bipyrrolidine D-tartrate trihydrate, 32 C C FW (S,S)-(+)-2,5 Bis(methoxymethyl) pyrrolidine, 97.0% (GC, sum of enantiomers) [ ] C FW C Butyl (S)-( )-2 pyrrolidone- 5 carboxylate, [ ] C FW (R)-( )---3 pyrrolidinol, [ ] C FW C 3 (R)-3-(-amino)pyrrolidine, 98.0% (TLC) [ ] C FW (S)-3-(-amino)pyrrolidine, 98.0% (TLC) [ ] C FW ,4 difluoro-l-proline, [ ] C F 2 4 FW oxo-l-proline, [ ] C FW F F sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

13 --trans-4 fluoro-l-proline, (R)-(+)-1 Benzyl-3 pyrrolidinol, (S)-(+)-1 Benzyl-3 aminopyrrolidine, [ ] C F 4 FW F --cis-4 fluoro-l-proline, [ ] C F 4 FW F (R)-(+)-1-2 pyrrolidinecarbonitrile, [ ] C FW (S)-( )-1 Benzyl-3 pyrrolidinol, [ ] C FW [ ] C FW (R)-( )-1 Benzyl-3 aminopyrrolidine, 95% [ ] C FW eterocyclic Building Blocks C FW C (S)-( )-1-2 pyrrolidinecarbonitrile, [ ] C FW (R)-2-(Azidomethyl)-1 pyrrolidine, 95% (PLC) [ ] C FW (S)-2-(Azidomethyl)-1 pyrrolidine, 95% (PLC) [ ] C FW (S)---2 methylpyrrolidine, 95% [ ] C FW C 3 3 C 3 [ ] C FW (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) [ ] C FW (p-Tosyl)-(R)-( )-3 pyrrolidinol, [ ] C S FW S C 3 (R)-( )-2-(Anilinomethyl)pyrrolidine, [ ] C FW oxo-L-proline methyl ester, [ ] C FW trans-4-fluoro-l-proline methyl ester, [ ] C 11 18F 4 FW (S)-( )-1-3 acetamidopyrrolidine, [ ] C FW (R)-(+)-1-3 acetamidopyrrolidine, F 8 C 3 8 [ ] C FW C Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 13

14 (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 FW C (S)-1-[(1 Methyl-2 pyrrolidinyl) methyl]piperidine, [ ] C FW (R)-( )-1 Cbz-3 pyrrolidinol, 95% [ ] C FW (1 R,3R)-(+)-1-(1 -Phenylethyl)- 5 oxo-3 pyrrolidinecarboxylic acid, [ ] C FW C [ ] C FW (S)-( )-1-(2 Methoxybenzoyl)-2- (methoxymethyl)pyrrolidine, [ ] C FW C 3 [ ] C FW Cbz (S)-( )-1-(2 Methoxybenzoyl)- 2 pyrrolidinemethanol, (R)---2 phenylpyrrolidine [ ] C FW (S)-(+)-1 Cbz-3 pyrrolidinol, 95% [ ] C FW (S)-(+)-5-(ydroxymethyl)- 2 pyrrolidinone p-toluenesulfonate, 95% [ ] C S FW C S Cbz (R)-( )-1 Cbz-3 aminopyrrolidine, C FW Cbz (S)-(+)-1 Cbz-3 aminopyrrolidine, C FW Cbz 2 2 [ ] C FW (R)-(+)-1-(2 Methoxybenzoyl)- 2 pyrrolidinemethanol, [ ] C FW (R)-(+)-1 Benzyl-3 acetylaminopyrrolidine, [ ] C FW (1R,2S)-1 Phenyl-2-(1 pyrrolidinyl)- 1 propanol, [ ] C FW (S)-( )-1 Benzyl-3-(-amino) pyrrolidine, C FW (R)-(+)-1 Benzyl-3-(-amino) pyrrolidine, [ ] C FW (R)-(+)-2-(Fluorodiphenylmethyl) pyrrolidine, [ ] C F FW F 14 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

15 (S)-( )-2-(Fluorodiphenylmethyl) pyrrolidine, [ ] C F FW (S)-( )-α,α-diphenyl-2 pyrrolidinemethanol, [ ] C FW Benzyl (S)-( )-2-(1 pyrrolidinylcarbonyl)-1 pyrrolidinecarboxylate, [ ] C FW F Cbz (R)-( )-1 Fmoc-3 pyrrolidinol, 95% [ ] C FW Fmoc (S)-(+)-1 Fmoc-3 pyrrolidinol, 95% [ ] C FW Methyl (2S)-( )-2-(hydroxydiphenylmethyl)-1 pyrrolidinecarboxylate, [ ] C FW C Fmoc (S)-(+)-5-(Trityloxymethyl)- 2 pyrrolidinone, [ ] C FW (S)-(+)---3--Fmoc-aminopyrrolidine, [ ] C FW (R)-( )---3--Fmoc-aminopyrrolidine, [ ] C FW Fmoc Fmoc eterocyclic Building Blocks 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 Tf 2 (0.05 mol %) C 2 2, 1 h TMS TMS Si TMS TTMSS TTMSS 75% syn:anti >95/5 TTMSS Boxer, M. B.; Yamamoto,. J. Am. Chem. Soc. 2006, 128, 48. For product-related inquiries, please contact our Technical Services department at (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

16 Quinuclidines eterocyclic Building Blocks (R)-( )-3 Quinuclidinol hydrochloride, [ ] C 7 13 FW (S)-( )-3 Aminoquinuclidine dihydrochloride, [ ] C FW (R)-(+)-3 Aminoquinuclidine dihydrochloride, [ ] C FW (2R,4S,5R)-2 Aminomethyl-5 ethylquinuclidine, 95.0% (GC) [ ] C FW C (R)-( )-3 Quinuclidinyl benzilate [ ] C FW C003 Ph Ph Thiophenes (1R)-1-(2 Thienyl)ethanol, 98.5% (GC) -(R)-2-thienylglycine, 8 -(R)-3-thienylglycine, 8 [ ] C 6 8 S FW S C 3 [ ] C S FW S [ ] C S FW S (1S)-1-(2 Thienyl)ethanol, 98.5% (GC) -(S)-2-thienylglycine, 8 -(S)-3-thienylglycine, 8 [ ] C 6 8 S FW S [ ] C S FW S C S FW S 16 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

17 thers D-ydroorotic acid, [ ] C FW (1S,4S)-(+)-2,5 Diazabicyclo[2.2.1] heptane dihydrobromide, [ ] C Br FW (2R,5S)-2 Trichloromethyl-3 oxa- 1 azabicyclo[3.3.0]octan-4 one, 98.0% (AT) [ ] C FW C 2Br (S)-1,4 Benzodioxane-2 carboxylic acid, 97.0% (GC, sum of enantiomers) [ ] C FW Sepiapterin [ ] C FW S154 3C D-(+)-eopterin, 97.5% (PLC, sum of enantiomers) [ ] C FW (3S-cis)-(+)-2,3 Dihydro-3 isopropyl-7a-methylpyrrolo[2,1-b]oxazol-5(7a)-one, [ ] C FW C 3 3C C 3 (3S-cis)-(+)-Tetrahydro-3 isopropyl- 7a-methylpyrrolo[2,1-b]oxazol-5 (6)-one, 95% [ ] C FW C C 3 (1S,4S)-( )-2-2,5 diazabicyclo [2.2.1]heptane, 95% eterocyclic Building Blocks (+)-6 Aminopenicillanic acid, 96% [ ] C S FW A S C 3 C (R)-2,5 Dihydro-3,6 dimethoxy- 2 isopropylpyrazine, 97.0% (GC) [ ] C FW C C 3 C 3 C 3 [ ] C FW ( )-p-bromolevamisole oxalate, (R)-(+)-1,2 Dithiolane-3 pentanoic acid, [ ] C S 2 FW S S (R)-1,4 Benzodioxane-2 carboxylic acid, 97.0% (GC, sum of enantiomers) [ ] C FW (S)-2,5 Dihydro-3,6 dimethoxy- 2 isopropylpyrazine, 97.0% (GC) [ ] C FW C C 3 C 3 (3R-cis)-( )-2,3 Dihydro-3 isopropyl-7a-methylpyrrolo[2,1-b]oxazol-5(7a)-one, [ ] C FW C 3 C 3 Br [ ] C 11 11Br 2S C FW S (1S,4S)-( )-2-(4 Chlorophenyl)- 2,5 diazabicyclo[2.2.1]heptane hydrobromide [ ] C Br FW Br C Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 17

18 (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 [ ] C F 2 Br FW (1S,4S)-( )-2-(4 Fluorophenyl)- 2,5 diazabicyclo[2.2.1]heptane hydrobromide [ ] C F 2 Br FW Br F Br [ ] C Br FW Br Br (1S,4S)-( )-2-(4 Methylphenyl)- 2,5 diazabicyclo[2.2.1]heptane maleate salt, 95% [ ] C C FW C 3 [ ] C FW C 3 (3S-cis)-(+)-2,3 Dihydro-7a-methyl- 3 phenylpyrrolo[2,1-b]oxazol-5 (7a)-one, [ ] C FW (4R,5S)-( )-1,5 Dimethyl-4 phenyl- 2 imidazolidinone, F (2R,4R)-(+)-4,5 Dihydro-4 iso- propyl-2-(p-tolyl)- 1,2λ 4,3 oxathiazole 2 oxide, Benzyl (S,S,S)-2 azabicyclo[3.3.0] octane-3 carboxylate hydrochloride, [ ] C FW C [ ] C S FW S [ ] C FW (4S,5R)-(+)-1,5 Dimethyl-4 phenyl- 2 imidazolidinone, [ ] C FW C (2S,4S)-4,5 Dihydro-4 isopropyl-2- (p-tolyl)-1,2λ 4,3 oxathiazole 2 oxide, [ ] C S FW C S ( )--(1(R)-Phenylethyl)-1 azabicyclo[2.2.2]octan-3(s)-amine dihydrochloride, [ ] C FW C 3 2 C (S)-(+)-2,3 Dihydro-1-pyrrolo[2,1- c][1,4]benzodiazepine-5,11 (10,11a)-dione, [ ] C FW (S)-( )-9,10 Difluoro-2,3 dihydro- 3 methyl-7 oxo-7-pyrido-[1,2,3- de]-1,4 benzoxazine-6 carboxylic acid, [ ] C 13 9F 2 4 FW F F C 3 (+)--(1(S)-Phenylethyl)-1 azabicyclo[2.2.2]octan-3(r)-amine dihydrochloride, [ ] C FW Aloperine, 96% 2 (S)-( )-1 Z-2 xo-5 imidazolidinecarboxylic acid, [ ] C FW Cbz C 3 [ ] C FW sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

19 (2S-cis)-(+)-2,3 Dihydro-3 hydroxy- 2-(4 methoxyphenyl)-1,5 benzothiazepin-4(5)-one, [ ] C S FW (+)-Usnic acid, [ ] C FW C 3C S 3C C 3 C 3 (3S-cis)-(+)-Tetrahydro-3,7adiphenylpyrrolo[2,1-b]oxazol-5 (6)-one, [ ] C FW (2S)-( )-2,2 -xybis(octahydro- 7,8,8 trimethyl-4,7 methanobenzofuran), [ ] C FW C C 3 3C C 3 3C 3C Ergotamine D-tartrate, 97.0% (T, calc. based on dry substance) Ph 3C [ ] C C FW ½ eterocyclic Building Blocks 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 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

20 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 In 0, Br TF/ 2, rt, 1 h R 81-96% > diastereoselectivity S Ph Bn Bn CF 3 C 2 0 C, 3 h Ph TBDMS 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 % (1) ili, R.; Yudin, A. K. J. Am. Chem. Soc. 2006, 128, (2) Yudin, A. K.; ili, R. Chem. Eur. J. 2007, 13, (3) Li, X.; Yudin, A. K. J. Am. Chem. Soc. 2007, 129, (4) ili, R.; Yudin, A. K. Angew. Chem., Int. Ed. 2008, 47, sigma-aldrich.com

21 rganic Building Blocks Acid alides (S)-( )-2 Acetoxypropionyl chloride, [ ] C FW (R)-( )--Formylmandeloyl chloride, [ ] C FW C C 3 (1S)-( )-Camphanic chloride, [ ] C FW C 3C 3C (S)-(+)-α-Methoxy-α-trifluoromethylphenylacetyl chloride, [ ] C 10 8F 3 2 FW (1S)-(+)-Menthyl chloroformate [ ] C FW C (1R)-( )-Menthyl chloroformate [ ] C FW C CF 3 3C C 3 C 3 ( )-Menthoxyacetyl chloride, [ ] C FW C ( )-1-(9 Fluorenyl)ethyl chloroformate solution [ ] C FW (+)-1-(9 Fluorenyl)ethyl chloroformate solution [ ] C FW C 3 C 3 3C rganic Building Blocks C Alcohols (S)-(+)-2 Chloro-1 propanol, [ ] C 3 7 FW C (R)-( )-3 Bromo-2 methyl-1 propanol, [ ] C 4 9Br FW Br (S)-(+)-2 Butanol, [ ] C 4 10 FW C (R)-(+)-3 Butyn-2 ol, [ ] C 4 6 FW (S)-( )-3 Butyn-2 ol, [ ] C 4 6 FW C 3C (S)-1,4 Dibromo-2 butanol, 95.0% (GC, sum of enantiomers) C C (S)-(+)-3 Bromo-2 methyl-1 propanol, [ ] C 4 9Br FW (R)-( )-2 Butanol, [ ] C 4 10 FW Br 3C C 3 (R)-( )-1 Methoxy-2 propanol, 98.5% (GC, sum of enantiomers) [ ] C FW C (S)-(+)-1 Methoxy-2 propanol, 98.5% (sum of enantiomers) [ ] C FW C [ ] C 4 8 Br 2 FW Br Br Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 21

22 rganic Building Blocks (R)-( )-4 Penten-2 ol, 95% [ ] C 5 10 FW (S)-(+)-4 Penten-2 ol, 95% [ ] C 5 10 FW C 2C (R)-5 Chloro-2 pentanol, 95% (GC, sum of enantiomers) [ ] C 5 11 FW (S)-(+)-2 Pentanol, [ ] C 5 12 FW C C 3 (R)-( )-2,2 Dimethyl-1,3 dioxolane- 4 methanol, [ ] C FW C C 3 (R)-6 Chloro-2 hexanol, 98.0% (GC, sum of enantiomers) [ ] C 6 13 FW (S)-(+)-2 exanol, [ ] C 6 14 FW C (S)-(+)-4 Methyl-2 pentanol, [ ] C 6 14 FW C C 3 (+)-endo-2 orborneol, 96% [ ] C 7 12 FW (1R,2R)-trans-2 Acetoxy-1 cyclopentanol, 99.0% (GC, sum of enantiomers) [ ] C FW (S)-( )-1,1,1 Trifluoroheptan-2 ol, [ ] C 7 13F 3 FW C 3(C 2) 3C 2 (4R)-4-(2 ydroxyethyl)-2,2 dimethyl-1,3 dioxolane, 96% CF 3 (R)-( )-2 Pentanol, [ ] C 5 12 FW C (S)-( )-2 Methyl-1 butanol, (R)-( )-4 Methyl-2 pentanol, [ ] C 6 14 FW C 3C C 3 [ ] C FW C C 3 (4S)-(+)-4-(2 ydroxyethyl)-2,2 dimethyl-1,3 dioxolane, 96% [ ] C 5 12 FW A83407 (S)-(+)-5 exen-2 ol, [ ] C 6 12 FW (R)-( )-5 exen-2 ol, [ ] C 6 12 FW C 2C 3C C 3 C 3 (S)-(+)-1,2 Isopropylideneglycerol, [ ] C FW C (R)-( )-2 exanol, [ ] C 6 14 FW C (1S,4R)-cis-4 Acetoxy-2 cyclopenten-1 ol, [ ] C FW (1R,4S)-cis-4 Acetoxy-2 cyclopenten-1 ol, 98.0% (GC, sum of enantiomers) [ ] C FW C C 3 [ ] C FW C C 3 (4S,5S)-2,2 Dimethyl-1,3 dioxolane-4,5 dimethanol, 97.0% (GC, sum of enantiomers) [ ] C FW (R)-( )-2 eptanol, 95% [ ] C 7 16 FW C C 3 (C2)3C sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

23 (S)-(+)-2 eptanol, [ ] C 7 16 FW (C2)3C2 (R)-( )-2-[(RS)-1 Ethoxyethoxy]- 1 propanol, 95.0% (GC, sum of enantiomers) [ ] C FW C 3C (S)-4 Bromo-α-methylbenzyl alcohol, 95% [ ] C 8 9 Br FW Br (S)-(+)-2 Chloro-1 phenylethanol, 97.0% (GC, sum of enantiomers) [ ] C 8 9 FW C 3 (R)-1 Phenylethanol, [ ] C 8 10 FW (S)-1 Phenylethanol, [ ] C 8 10 FW (S)-( )-1 ctyn-3 ol, rganic Building Blocks (R)-( )-α-(trifluoromethyl)benzyl alcohol, [ ] C 8 7F 3 FW CF3 (R)-( )-2 Chloro-1 phenylethanol, [ ] C 8 9 FW [ ] C 8 14 FW (R)-(+)-1 ctyn-3 ol, (C2)3C2 C (S)-(+)-α-(Trifluoromethyl)benzyl alcohol, (R)-4 Chloro-α-methylbenzyl alcohol, 95% [ ] C 8 14 FW C 3(C 2) 3C 2 C [ ] C 8 7F 3 FW (R)-(+)-2 Bromo-α-methylbenzyl alcohol, [ ] C 8 9Br FW (S)-( )-2 Bromo-α-methylbenzyl alcohol, [ ] C 8 9 Br FW Br (R)-4 Bromo-α-methylbenzyl alcohol, 95% [ ] C 8 9 Br FW Br Br CF3 C 3 C 3 [ ] C 8 9 FW (S)-4 Chloro-α-methylbenzyl alcohol, 95% [ ] C 8 9 FW (S)-4 Fluoro-α-methylbenzyl alcohol, [ ] C 8 9 F FW F (R)-4 Fluoro-α-methylbenzyl alcohol, [ ] C 8 9F FW F C 3 C 3 (R)-(+)-1,1,1 Trifluoro-2 octanol, [ ] C 8 15F 3 FW (C2)4C2 (S)-( )-1,1,1 Trifluoro-2 octanol, [ ] C 8 15F 3 FW (C2)4C2 (S)-1 cten-3 ol, 95% (PLC, sum of enantiomers) [ ] C 8 16 FW (C2)3C2 (R)-(+)-1 Fluoro-2 octanol, [ ] C 8 17F FW 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

24 (R)-( )-2 ctanol, (R)-( )-1 Indanol, (R)-(+)-1 Phenyl-1 propanol, [ ] C 8 18 FW C 3(C 2) 4C 2 C 3 [ ] C 9 10 FW [ ] C 9 12 FW rganic Building Blocks (S)-(+)-2 ctanol, [ ] C 8 18 FW (S)-(+)-3 ctanol, [ ] C 8 18 FW C (C2)4C2 C 3 (R)-1 Phenyl-2 propyn-1 ol, 99.0% (GC, sum of enantiomers) [ ] C 9 8 FW (S)-1 Phenyl-2 propyn-1 ol, 99.0% (GC, sum of enantiomers) C (S)-1 Phenyl-2 propen-1 ol, 97.0% (GC, sum of enantiomers) [ ] C 9 10 FW (R)-1 Phenyl-2 propen-1 ol, 95% (GC, sum of enantiomers) [ ] C 9 10 FW (S)-( )-3 Chloro-1 phenyl-1 propanol, [ ] C 9 11 FW C 2 C (S)-( )-1 Phenyl-1 propanol, [ ] C 9 12 FW (R)-( )-1 Phenyl-2 propanol, 97.0% (GC, sum of enantiomers) [ ] C 9 12 FW (R)-(+)-2 Phenyl-1 propanol, [ ] C 9 12 FW (S)-( )-2 Phenyl-1 propanol, C 3 C 3 C 3 [ ] C 9 8 FW C (R)-(+)-3 Chloro-1 phenyl-1 propanol, [ ] C 9 12 FW C (S)-( )-1 Chloro-3-(4 fluorophenoxy)-2 propanol, [ ] C 9 11 FW (S)-(+)-1 Phenyl-2 propanol, 97.0% (GC, sum of enantiomers) [ ] C 9 10F 2 FW (R)-(+)-1 Chloro-3-(4 fluorophenoxy)-2 propanol, [ ] C 9 10 F 2 FW (S)-(+)-1 Indanol, F F (S)-(+)-1-(4 Fluorophenoxy)-2 propanol, [ ] C 9 11F 2 FW F (R)-( )-1-(4 Fluorophenoxy)-2 propanol, [ ] C 9 11 F 2 FW F C 3 [ ] C 9 12 FW (S)-(+)-2 Methoxy-2 phenylethanol, [ ] C FW (R)-( )-2 Methoxy-2 phenylethanol, C 3 [ ] C 9 10 FW [ ] C FW sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

25 D-α,β-Cyclohexylideneglycerol, 98.0% (GC, sum of enantiomers) [ ] C FW (S)-(+)-2 onanol, [ ] C 9 20 FW C (R)-( )-2 onanol, [ ] C 9 20 FW C (R)-1-[3,5 Bis(trifluoromethyl)phenyl]ethanol, 98.0% (GC) [ ] C 10 8F 6 FW F 3C CF3 (S)-(+)-1,2,3,4 Tetrahydro-1 naphthol, [ ] C FW (S)-(+)-4 Phenyl-2 butanol, [ ] C FW (R)-( )-4 Phenyl-2 butanol, [ ] C FW (R)-( )-1 Benzyloxy-2 propanol, [ ] C FW C (S)-(+)-1 Benzyloxy-2 propanol, [ ] C FW C (R)-Glycerol 1-(p-toluenesulfonate), 95% (TLC) [ ] C S FW G2410 3C S C 3 C 3 ( )-trans-pinocarveol, 96.0% (GC, sum of enantiomers) [ ] C FW (S)-cis-Verbenol, 95% [ ] C FW (+)-Borneol, [ ] C FW ( )-Borneol, [ ] C FW C 3C 3C (1S,2S,5S)-( )-Myrtanol, [ ] C FW C C 3 C 2 C 3 3C 3C 3C rganic Building Blocks (R)-( )-1,2,3,4 Tetrahydro-1 naphthol, [ ] C FW (R)-(+)-1 Phenyl-1 butanol, [ ] C FW (S)-( )-1 Phenyl-1 butanol, C 3 (S)-( )-Perillyl alcohol, 96% [ ] C FW (1R)-( )-Myrtenol, 95% [ ] C FW C 3C ( )-Carveol, mixture of isomers, (1R)-endo-(+)-Fenchyl alcohol, 96% [ ] C FW (+)-Dihydrocarveol, 95.0% (GC, sum of enantiomers) [ ] C FW C 3C C 3 C 3 C 3 [ ] C FW [ ] C FW C 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

26 rganic Building Blocks ( )-Dihydrocarveol, 95.0% (GC, sum of enantiomers) [ ] C FW (+)-Isopulegol, [ ] C FW ( )-Isopulegol, 2C 2C C 3 C 3 (1S,2S,3S,5R)-(+)-Isopinocampheol, [ ] C FW C 3C (1R,2R,3R,5S)-( )-Isopinocampheol, [ ] C FW C 3C C 3 (R)-( )-2 Decanol, [ ] C FW (C2)6C2 (S)-3 Butene-1,2 diol-1-(p-toluenesulfonate), 99.0% (PLC) [ ] C S FW C S (R)-3 Butene-1,2 diol-1-(p-toluenesulfonate), 99.0% (PLC) C 2 [ ] C FW C ( )-Linalool, 95.0% (GC, sum of enantiomers) [ ] C FW α-terpineol, 90% [ ] C FW C 3 3C C2 3C 3C 3C C 3 (1S,2S,4R)-(+)-Limonene-1,2 diol, 97.0% (GC) [ ] C FW (R)-(+)-β-Citronellol, [ ] C FW C (S)-( )-β-citronellol, [ ] C FW C 2C C 3 C 3 [ ] C S FW C (1R)-( )-opol, [ ] C FW S 3C 2 Methylisoborneol solution, (GC) [ ] C FW C C 3 3C C 2 ( )-Terpinen-4 ol, 95.0% (GC, sum of enantiomers) [ ] C FW Isoborneol, 95% [ ] C FW I C 3C C (1R,2S,5R)-( )-Menthol, [ ] C FW M2780 3C (1S,2R,5S)-(+)-Menthol, [ ] C FW C (1S,2S,5R)-(+)-eomenthol, [ ] C FW C C 3 C 3 C 3 C 3 C 3 C 3 M3933 (R)-(+)-α Methyl-1 naphthalenemethanol, [ ] C FW C (S)-( )-α Methyl-1 naphthalenemethanol, [ ] C FW C sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

27 (R)-(+)-1-(2 aphthyl)ethanol, [ ] C FW (S)-( )-α Methyl-2 naphthalenemethanol, [ ] C FW (1R,2S)-trans-2 Phenyl-1 cyclohexanol, C 3 (1S,2R)-(+)-trans-2-(1 Methyl- 1 phenylethyl)cyclohexanol, [ ] C FW C 3 (1R,2S)-( )-trans-2-(1 Methyl- 1 phenylethyl)cyclohexanol, [ ] C FW ( )-Guaiol, C 3 (S)-( )-1 Phenyl-1 decanol, 95% [ ] C FW (C2)7C2 (S)-( )-2,3 Dibenzyloxy-1 propanol, 96% [ ] C FW (S)-2 Benzyloxy-1,3 propanediol 1- (p-toluenesulfonate), 99.0% (PLC, sum of enantiomers) Ph Ph rganic Building Blocks [ ] C FW (1S,2R)-(+)-trans-2 Phenyl-1 cyclohexanol, [ ] C FW (S)-( )-1,1,1,2,2 Pentafluorododecan-3 ol, [ ] C 12 21F 5 FW (C2)7C2 (S)-( )-1-(9 Fluorenyl)ethanol, 99.0% (PLC) [ ] C FW C CF2CF3 [ ] C FW C C 3 3C C 3 (R)-( )-1-(9 Anthryl)-2,2,2 trifluoroethanol, [ ] C F 3 FW CF 3 (S)-(+)-1-(9 Anthryl)-2,2,2 trifluoroethanol, [ ] C F 3 FW ( )-8 Phenylmenthol, [ ] C FW CF 3 3C C 3 [ ] C S FW C S (R)-( )-1 Benzyloxy-3-(p-tosyloxy)- 2 propanol, 95% 3C [ ] C S FW S (R)-(+)-1-(2,4,6 Triisopropylphenyl) ethanol, 96.0% (PLC) [ ] C FW i-pr i-pr i-pr (S)-(+)-1 Phenyl-1,2 ethanediol 2 tosylate, [ ] C S FW C S (+)-8 Phenylmenthol, 98.0% (PLC, sum of enantiomers) [ ] C FW C C Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 27

28 rganic Building Blocks (S)-( )-1-(2,4,6 Triisopropylphenyl) ethanol, 98.5% (PLC) [ ] C FW 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] C 3C (1R,2S,4R)-( )-4-(1 Methylethyl)-2- (1 methyl-1 phenylethyl)cyclohexanol, [ ] C FW C 3C (4bS)-trans-8,8 Trimethyl- 4b,5,6,7,8,8a,9,10 octahydro-1 isopropylphenanthren-2 ol, [ ] C FW C 3C (4aR)-trans-5-(1,5,5,8aS-Tetra- methyl-2 methylenedecahydro- 1 naphthalenyl)-(3r)-methyl- 1 penten-3 ol, [ ] C FW C 3C C 3 C2 C2 2,3 Dilauroyl-sn-glycerol, 99.0% (TLC) [ ] C FW C(2C) (C2)10 Aldehydes (R)-(+)-2,2 Dimethyl-1,3 dioxolane- 4 carboxaldehyde [ ] C FW (R)-1,4 Dioxaspiro[4.5]decane- 2 carboxaldehyde [ ] C FW C ( )-Myrtenal, 97.0% (GC, sum of enantiomers) [ ] C FW (+)-Perillaaldehyde, 98.0% (GC, sum of enantiomers) [ ] C FW C 3C (S)-( )-Perillaldehyde, 92% [ ] C FW (R)-(+)-Citronellal, 90% [ ] C FW C (S)-( )-Citronellal, 96% 2C C 3 (1R)-( )-Myrtenal, [ ] C FW C [ ] C FW C C 3 C sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

29 Amides (R)-(+)-Lactamide, [ ] C FW (S)-( )-Lactamide, [ ] C FW C 3C (S)-(+)-2 Aminobutanamide hydrochloride, 2 2 (+)-,,, -Tetramethyl-L-tartaric acid diamide, [ ] C FW C 3 3C C 3 2,2,2 Trifluoro--[(S)-α-methylbenzyl]acetamide, [ ] C 10 10F 3 FW CF3 (+)-, -Dibenzyl-L-tartaric diamide, [ ] C FW ( )-, -Dibenzyl-D-tartaric diamide, [ ] C FW rganic Building Blocks [ ] C FW C 2 2 (R)-( )-2 Aminobutanamide hydrochloride, [ ] C FW C 2 2 (+)-, -Diallyltartramide, [ ] C FW C (R)-( )-3,5 Dinitro--(1 phenylethyl)benzamide, [ ] C FW C 2 (R)-( )--[1-(1 aphthyl)ethyl]- 3,5 dinitrobenzamide, [ ] C FW (S)-(+)--[1-(1 aphthyl)ethyl]- 3,5 dinitrobenzamide, (R)-( )-2,2 Dimethylcyclopropane- 1 carboxamide, [ ] C 6 11 FW C (S)-(+)-2,2 Dimethylcyclopropanecarboxamide, [ ] C 6 11 FW C,,, -Tetramethyl-D-tartaramide, (S)-(+)-3,5 Dinitro--(1 phenylethyl)benzamide, [ ] C FW α-xo--[(r)-1 phenylethyl] phenylacetamide, [ ] C FW C 3 C 3 [ ] C FW ( )-, -Dibenzoyl-L-tartaric acid mono(dimethylamide), 99.0% (T) [ ] C FW C [ ] C FW C 3 3C C Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 29

30 Amines rganic Building Blocks (S)-(+)-sec-Butylamine, [ ] C 4 11 FW (R)-( )-sec-butylamine, [ ] C 4 11 FW C 3C (S)-( )-sec-butylamine hydrochloride, 98.0% (AT) C 4 11 FW C 2 2 C 3 2 C 3 (S)-( )-2 Methylbutylamine, 95% [ ] C 5 13 FW C (S)-(+)-2 Amino-3 methylbutane, 98.0% (GC) [ ] C 5 13 FW C (R)-( )-2 Amino-3 methylbutane, 97.0% (GC) [ ] C 5 13 FW C (S)-(+)-3,3 Dimethyl-2 butylamine, [ ] C 6 15 FW C 3C 3C (R)-( )-3,3 Dimethyl-2 butylamine, 2 (S)-2 Aminohexane, 97.0% (GC) [ ] C 6 15 FW C (R)-2 Aminohexane, 97.0% (GC) [ ] C 6 15 FW C (R)-( )-2 Aminoheptane, [ ] C 7 17 FW C (S)-(+)-2 Aminoheptane, [ ] C 7 17 FW C [ ] C 8 10 Br FW Br 2 (S)-( )-1-(4 Bromophenyl)ethylamine, 98.0% (GC, sum of enantiomers) (R)-(+)-1-(4 Bromophenyl)ethylamine, 96.0% (GC, sum of enantiomers) [ ] C 8 10 Br FW Br 2 C 3 C 3 C 3 C 3 (R)-4 Chloro-α-methylbenzylamine, 95.0% (GC) [ ] C 8 10 FW C 3 (S)-4 Chloro-α-methylbenzylamine, 95.0% (GC) [ ] C 8 10 FW (R)-α-Methyl-4 nitrobenzylamine hydrochloride, [ ] C FW (S)-α-Methyl-4 nitrobenzylamine hydrochloride, [ ] C FW C 3 C 3 2 (R)-(+)-α-Methylbenzylamine, [ ] C 8 11 FW (S)-( )-α-methylbenzylamine, [ ] C 8 11 FW (R)-( )-1 Cyclohexylethylamine, [ ] C 8 17 FW (S)-(+)-1 Cyclohexylethylamine, [ ] C 8 17 FW C 3 2 C 3 [ ] C 6 15 FW C 3C 3C sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

31 (R)-2 Aminooctane, 98.0% (GC) [ ] C 8 19 FW C (S)-2 Aminooctane, 97.0% (GC) [ ] C 8 19 FW C (S)-(+)-1 Aminoindan, [ ] C 9 11 FW (R)-( )-1 Aminoindane, [ ] C 9 11 FW (R)-(+)-,α-Dimethylbenzylamine, [ ] C 9 13 FW C 3 C 3 (S)-( )-,α-dimethylbenzylamine, [ ] C 9 13 FW C 3 (R)-(+)-α,4 Dimethylbenzylamine, [ ] C 9 13 FW C (R)-(+)-β-Methylphenethylamine, 2 C 3 (R)-( )-1,2,3,4 Tetrahydro-1 naphthylamine, [ ] C FW (S)-( )-,-Dimethyl-1 phenylethylamine, [ ] C FW (R)-(+)-,-Dimethyl-1 phenylethylamine, [ ] C FW C 3 (S)-(+)-α-(Methoxymethyl)phenethylamine hydrochloride, 2 C 3 C 3 rganic Building Blocks (S)-( )-α,4 Dimethylbenzylamine, [ ] C 9 13 FW C 2 (S)-β-Methylphenethylamine, [ ] C 9 13 FW C 3 C 3 2 [ ] C 9 13 FW (S)-( )-4 Methoxy-α-methylbenzylamine, 98.0% (GC, sum of enantiomers) [ ] C 9 13 FW C 2 [ ] C FW (R)-(+)-Bornylamine, [ ] C FW C 3C (1R,2R,3R,5S)-( )-Isopinocampheylamine, 95% 2 (S)-( )-α-ethylbenzylamine, 95.0% (GC) [ ] C 9 13 FW (R)-(+)-α-Ethylbenzylamine, 99.0% (GC) [ ] C 9 13 FW C 3 2 C 3 (R)-(+)-4 Methoxy-α-methylbenzylamine, 95.0% (GC) [ ] C 9 13 FW C (S)-(+)-1,2,3,4 Tetrahydro-1 naphthylamine, [ ] C FW C 3 2 [ ] C FW C 3C C 3 2 (1S,2S,3S,5R)-(+)-Isopinocampheylamine, 95% [ ] C FW C 3C Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 31

32 rganic Building Blocks ( )-cis-myrtanylamine, [ ] C FW (R)-( )-Isobornylamine hydrochloride, 97.0% (AT) [ ] C FW C C 3 2 3C 2 (R)-(+)-1-(1 aphthyl)ethylamine hydrochloride, [ ] C FW C 2 (S)-( )-1-(1 aphthyl)ethylamine hydrochloride, [ ] C FW C 2 (S)-( )-,-Dimethyl-1-(1 naphthyl)ethylamine, [ ] C FW C (R)-(+)-,-Dimethyl-1-(1 naphthyl)ethylamine, 96% [ ] C FW C C 3 (R)-(+)--allyl-α-methylbenzylamine, [ ] C FW C 2 (1S,2S)-trans-2 Benzyloxycyclopentylamine, [ ] C FW (R)-1,1 Diphenyl-1 fluoro-2 aminopropane, C F FW F 2 (R)-(+)-1-(1 aphthyl)ethylamine, [ ] C FW C (S)-( )-1-(1 aphthyl)ethylamine, [ ] C FW C 2 (R)-(+)-1-(2 aphthyl)ethylamine, 99.0% (GC, sum of enantiomers) [ ] C FW (S)-( )-1-(2 aphthyl)ethylamine, 99.0% (GC, sum of enantiomers) C 3 (R)-(+)--Methyl-1-(1 naphthyl) ethylamine, [ ] C FW C (S)-( )--Methyl-1-(1 naphthyl) ethylamine, [ ] C FW C (4S,5S)-(+)-2,2 Dimethyl-5 methylamino-4 phenyl-1,3 dioxane, 98.0% (GC, sum of enantiomers) [ ] C FW C C 3 C (S)-1,1 Diphenyl-1 fluoro-2 aminopropane, C F FW (R)-(+)-1,1 Diphenyl-2 aminopropane, C FW (S)-( )-1,1 Diphenyl-2 aminopropane, [ ] C FW F 2 C 3 2 C 3 2 [ ] C FW C sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

33 (S)-( )--Benzyl-α-methylbenzylamine, (R)-(+)-2 Amino-1 fluoro-3 methyl- 1,1 diphenylbutane, (R)-(+)-2 Amino-4 methyl- 1,1 diphenylpentane, [ ] C FW (R)-(+)--Benzyl-α-methylbenzylamine, [ ] C FW C 17 20F FW C (S)-( )-2 Amino-3 methyl- 1,1 diphenylbutane, [ ] C FW C C F [ ] C FW (S)-( )-2 Amino-4 methyl- 1,1 diphenylpentane, [ ] C FW C 2 3C rganic Building Blocks (+)-Bis[(R)-1 phenylethyl]amine, [ ] C FW C 3 ( )-Bis[(S)-1 phenylethyl]amine, (R)-(+)-2 Amino-3 methyl- 1,1 diphenylbutane, [ ] C FW C (R)-( )--Benzyl-1-(1 naphthyl) ethylamine hydrochloride, [ ] C FW C [ ] C FW (S)-( )-2 Amino-1 fluoro-4 methyl- 1,1 diphenylpentane, (S)--Benzyl-1-(1 naphthyl)ethylamine hydrochloride, 96.0% (AT) (+)-Bis[(R)-1 phenylethyl]amine hydrochloride, [ ] C 18 22F FW C 3 2 3C F [ ] C FW C [ ] C FW ( )-Bis[(S)-1 phenylethyl]amine hydrochloride, (R)-(+)-2 Amino-1 fluoro-4 methyl- 1,1 diphenylpentane, [ ] C F FW C C 3 2 F (S)-( )-1,2,2 Triphenylethylamine, [ ] C FW [ ] C FW (S)-( )-2 Amino-1 fluoro-3 methyl- 1,1 diphenylbutane, C F FW C 2 F (S)-(+)-2 Amino-3,3 dimethyl- 1,1 diphenylbutane, [ ] C FW t-bu (R)-(+)-1,2,2 Triphenylethylamine, C FW Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 33

34 (R)-(+)-1 Benzyl-2,2 diphenylethylamine, (R)-, -Dimethyl-1,1 -binaphthyldiamine, 99.0% Bis[(R)-( )-(1 naphthyl)ethyl]amine hydrochloride, rganic Building Blocks [ ] C FW (S)-( )-1 Benzyl-2,2 diphenylethylamine, [ ] C FW [ ] C FW (S)-, -Dimethyl-1,1 -binaphthyldiamine, 99.0% [ ] C FW [ ] C FW C 3 Bis[(S)-(+)-(1 naphthyl)ethyl]amine hydrochloride, [ ] C FW C Amino Alcohols (R)-( )-1 Amino-2 propanol, [ ] C 3 9 FW C 2 (R)-( )-2 Amino-1 butanol, [ ] C 4 11 FW C 2 (R)-( )-2 Amino-3 methyl-1 butanol, [ ] C 5 13 FW C 2 (S)-(+)-1 Amino-2 propanol, (S)-(+)-2 Amino-1 butanol, [ ] C 3 9 FW C (R)-( )-2 Amino-1 propanol, [ ] C 3 9 FW C 2 [ ] C 4 11 FW C 2 (1R,2R)-trans-2 Aminocyclopentanol hydrochloride, [ ] C 5 11 FW (S)-(+)-2 Amino-3 methyl-1 butanol, 96% [ ] C 5 13 FW C C 3 (S)-(+)-1 Dimethylamino-2 propanol, 2 (S)-(+)-2 Amino-1 propanol, [ ] C 3 9 FW A C 2 (S)-3 Amino-1,2 propanediol, [ ] C FW (R)-3 Amino-1,2 propanediol, 98.0% (T) [ ] C FW (1S,2S)-trans-2 Aminocyclopentanol hydrochloride, 98.0% (TLC) [ ] C 5 11 FW (1R,2S)-cis-2 Aminocyclopentanol hydrochloride, 98.0% (TLC) [ ] C 5 11 FW [ ] C 5 13 FW C (S)-(+)-2 Amino-1 pentanol, [ ] C 5 13 FW C (R)-( )-2 Amino-1 pentanol, [ ] C 5 13 FW C sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

35 (1S,2S)-(+)-2 Aminocyclohexanol hydrochloride, % (AT) (S)-(+)-orepinephrine L-bitartrate, (1S,2S)-(+)-trans-1 Amino-2 indanol, [ ] C 6 13 FW (1R,2R)-trans-2 Aminocyclohexanol hydrochloride, [ ] C 6 13 FW (S)-( )-(3 Chloro-2 hydroxypropyl) trimethylammonium chloride, [ ] C FW (S)-(+)-2 Amino-1 hexanol, [ ] C 6 15 FW C (R)-( )-2 Amino-1 hexanol, [ ] C 6 15 FW C (S)-( )-3-tert-Butylamino- 1,2 propanediol, [ ] C FW C C (R)-( )-2 Amino-1 phenylethanol, [ ] C 8 11 FW (S)-2 Amino-1 phenylethanol, 97.0% (GC, sum of enantiomers) [ ] C 8 11 FW [ ] C C FW orepinephrine L-bitartrate hydrate, 2 x 2 [ ] C C x 2 FW (Anh) (S)-2-(-amino)-1 propanol, [ ] C FW C (1S,2R)-( )-cis-1 Amino-2 indanol, [ ] C 9 11 FW (1R,2S)-(+)-cis-1 Amino-2 indanol, [ ] C 9 11 FW (1R,2R)-( )-trans-1 Amino-2 indanol, [ ] C 9 11 FW [ ] C 9 11 FW (R)-( )-1 Amino-6 hydroxyindan, C 9 11 FW (1R,2R)-( )-2 Amino-1-(4 nitrophenyl)-1,3 propanediol, [ ] C FW A (1S,2S)-(+)-2 Amino-1-(4 nitrophenyl)-1,3 propanediol, [ ] C FW (S)-( )-2 Amino-3 phenyl-1 propanol, [ ] C 9 13 FW (R)-(+)-2 Amino-3 phenyl-1 propanol, [ ] C 9 13 FW (1S,2S)-(+)-2 Amino-1 phenyl- 1,3 propanediol, [ ] C FW rganic Building Blocks Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 35

36 (1R,2R)-( )-2 Amino-1 phenyl- 1,3 propanediol, (1S,2S)-trans---2 aminocyclopentanol (R)-( )-2-tert-Butylamino-1 phenylethanol, rganic Building Blocks [ ] C FW (S)-(+)-2 Amino-3 cyclohexyl-1 propanol hydrochloride, [ ] C 9 19 FW (S)-( )-2 amino-1 butanol, 96% [ ] C FW C [ ] C FW (1R,2R)-trans---2 aminocyclopentanol, 98.5% (GC) [ ] C FW (S)-( )-2-(-amino)-1,5 pentanediol, [ ] C FW [ ] C FW C 3 C 3 (S)-(+)-2-tert-Butylamino-1 phenylethanol, [ ] C FW (S)-(+)-2 Amino-2-(4-tert-butylphenyl)ethanol, C FW C 3C C 3 C (R)-(+)-2 amino-1 butanol, 96% C FW C (S)-( )-2-(-amino)-1,4 butanediol, [ ] C FW (1S,2S)-(+)-2 Amino-3 methoxy- 1 phenyl-1 propanol, [ ] C FW C 3 2 (R)-(+)-2 Amino-3 benzyloxy-1 propanol, [ ] C FW (1S,2S)-(+)-Thiomicamine, [ ] C S FW CS 2 2 (1S,2S)-trans---2 aminocyclohexanol, [ ] C FW (1R,2R)-trans---2 aminocyclohexanol, [ ] C FW (2S,3S)-( )-2 amino-3 methyl-1 pentanol, 96% [ ] C FW C (+)-2 Amino--[(1S,2S)-(2 hydroxy- 1 methyl-2 phenyl)ethyl]-methylacetamide, [ ] C FW C C (1S,2R)-(+)-2 Amino-1,2 diphenylethanol, [ ] C FW (1R,2S)-( )-2 Amino-1,2 diphenylethanol, [ ] C FW (S,S)-( )-2 Amino-1,2 diphenylethanol, 99.5% (PLC) [ ] C FW (R,R)-(+)-2 Amino-1,2 diphenylethanol, 99.5% (PLC) [ ] C FW sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

37 (1R,2R)-( )---2 amino-1- (4 nitrophenyl)-1,3 propanediol, 96% [ ] C FW cis-(1s,2r)-( )-2-(Benzylamino) cyclohexanemethanol, [ ] C FW (R)-( )-2 Benzylamino-1 phenylethanol, [ ] C FW (S)-(+)-2 Benzylamino-1 phenylethanol, [ ] C FW (S)-( )-2 Amino-4 methyl-1,1 diphenyl-1 pentanol, [ ] C FW C (S)-( )-2 Amino-3,3 dimethyl- 1,1 diphenyl-1 butanol, [ ] C FW t-bu 2 rganic Building Blocks (1S,2S)-(+)---2 amino-1 phenyl-1,3 propanediol, C FW (R)-(+)-Atenolol, 3C [ ] C FW (S)-( )-2-(-amino)-3 cyclohexyl- 1 propanol, 90% [ ] C FW (R)-(+)-2 Amino-1,1 diphenyl- 1 propanol, [ ] C FW C 3 (R)-(+)-3 Benzyloxy-2-(-amino)- 1 propanol, [ ] C FW (R)-(+)-2 Amino-3 methyl-1,1 diphenyl-1 butanol, [ ] C FW C 2 (S)-( )-2 Amino-3 methyl-1,1 diphenyl-1 butanol, [ ] C FW C C 3 2 (S)-(+)-2-(Dibenzylamino)-1 propanol, [ ] C FW C (2R,3S)-( )-4 Dimethylamino- 1,2 diphenyl-3 methyl-2 butanol, [ ] C FW Chirald, [ ] C FW (S)-2-(,-Dibenzylamino)- 3 methylbutanol, 90% [ ] C FW C Ph Ph (S)-( )-2 Amino-1,1,2 triphenylethanol, [ ] C FW (S)-( )-2 Amino-1,1 diphenyl-1 propanol, [ ] C FW C 3 (R)-(+)-2 Amino-4 methyl-1,1 diphenyl-1 pentanol, [ ] C FW C (S)-(+)-2-(,-Dibenzylamino)- 4 methylpentanol, 90% [ ] C FW C C Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 37

38 (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 [ ] C FW (S)-( )-2 Amino-1,1,3 triphenyl- 1 propanol, [ ] C FW [ ] C FW (S)-( )--Carboxymethoxy-2 amino-1,1,2 triphenylethanol, C FW [ ] C FW 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.

39 Aziridines Lithium L-aziridine-2 carboxylate, 97.0% (T, dried material) [ ] C 3 4 Li 2 FW Li (S)-1-[(R)-α-Methylbenzyl)aziridine-2 carboxamide, [ ] C FW C (R)-1-[(1R)-α-Methylbenzyl]aziridine-2 carboxamide, [ ] C FW C Ph 2 2 (S)-1-[(R)-α-Methylbenzyl]aziridine-2 methanol, [ ] C FW C 1 Benzyl 2 methyl (S)-( )-1,2 aziridinedicarboxylate, 96% [ ] C FW Cbz (S)-(+)-2 Benzyl-1-(p-tolylsulfonyl) aziridine, [ ] C S FW S Ph ( )-Menthyl (R)-1-[(R)-α-methylbenzyl]aziridine-2 carboxylate, C FW C 3C ( )-Menthyl (S)-1-[(R)-α-methylbenzyl]aziridine-2 carboxylate, C FW C 3C C 3 C 3 rganic Building Blocks C 3 Methyl (S)-( )-1 tritylaziridine- 2 carboxylate, (R)-1-[(R)-α-Methylbenzyl)aziridine-2 methanol, [ ] C FW C Ph [ ] C FW C 3 Carboxylic Acids (S)-( )-Trifluorolactic acid, (S)-( )-2 Chloropropionic acid, Sodium L-lactate, 99.0% (T) [ ] C 3 3F 3 3 FW F3C [ ] C FW C [ ] C 3 5a 3 FW C a (R)-(+)-2 Bromopropionic acid, 98.0% (GC, sum of enantiomers) [ ] C 3 5 Br 2 FW C Br (S)-( )-2 Bromopropionic acid, [ ] C 3 5 Br 2 FW C Br (R)-(+)-2 Chloropropionic acid, [ ] C FW C Sodium D-lactate, 99.0% (T) [ ] C 3 5 a 3 FW C a L-( )-Glyceric acid hemicalcium salt monohydrate, (KT) [ ] C Ca 2 FW Ca Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 39

40 rganic Building Blocks L-(+)-2 Amino-3 phosphonopropionic acid [ ] C P FW A154 Potassium L-tartrate, [ ] C 4 4 K FW K P L-( )-Malic acid disodium salt, % (enzymatic) [ ] C 4 4a 2 5 FW a 2 K 2 a L-( )-Malic acid, [ ] C FW D-(+)-Malic acid, 97.0% (PLC, sum of enantiomers) [ ] C FW D-( )-Tartaric acid, [ ] C FW (S)-3 ydroxybutyric acid, 97.0% (T) [ ] C FW C (S)-(+)-4 Amino-3 hydroxybutyric acid, [ ] C FW (S)-( )-4 Amino-2 hydroxybutyric acid, 96% [ ] C FW M9138 L-Malic acid disodium salt monohydrate, [ ] C 4 4 a FW a a 2 Potassium L-tartrate monobasic, [ ] C 4 5K 6 FW Potassium D-tartrate monobasic [ ] C 4 5 K 6 FW T2032 L-( )-Malic acid sodium salt, % (enzymatic) [ ] C 4 5 a 5 FW M1125 K + - Sodium hydrogentartrate, [ ] C 4 5a 6 FW K a a L-(+)-Tartaric acid, [ ] C FW T109 (R)-( )-3 ydroxybutyric acid sodium salt [ ] C 4 7 a 3 FW C Sodium (S)-3 hydroxybutyrate, ~ [ ] C 4 7a 3 FW C (S)-(+)-2 Amino-4 bromobutyric acid hydrobromide, [ ] C 4 8Br 2 Br FW (R)-3 ydroxybutyric acid, 98.0% (T) [ ] C FW Br a a Br 2 3C (S)-( )-2 Formamidosuccinic anhydride, 90% [ ] C FW (R)-(+)-Methylsuccinic acid, [ ] C FW C 3 (S)-( )-Methylsuccinic acid, [ ] C FW (S)-( )-2 Acetoxypropionic acid, 95% [ ] C FW (R)-( )-Citramalic acid, [ ] C FW C C sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

41 (R)-(+)-2 Bromo-3 methylbutyric acid, 96% (S)-( )-2-(Trifluoroacetamido)succinic anhydride, (S)-( )-2 ydroxyisocaproic acid, [ ] C 5 9 Br 2 FW C C 3 (S)-( )-2 Bromo-3 methylbutyric acid, 96% [ ] C 5 9 Br 2 FW C Br C 3 (S)-2 Chloro-3 methylbutyric acid, 90% (GC) [ ] C FW Br 3C (R)-2 Chloro-3 methylbutyric acid, 90% (GC) [ ] C FW C (S)-(+)-2 Methylbutyric acid, [ ] C FW C C 3 (S)-(+)-2 ydroxy-3 methylbutyric acid, [ ] C 6 4 F 3 4 FW (S)-( )-2 Acetoxysuccinic anhydride, [ ] C FW (R)-(+)-2 Acetoxysuccinic anhydride, 96% [ ] C FW CF3 C 3 (+)-Potassium D s -threo-isocitrate monobasic, 98.0% (T) [ ] K C 6 7 K 7 FW Calcium L-lactate hydrate, 98.0% (KT, calc. based on dry substance) [ ] C 6 10 Ca 6 x 2 FW (Anh) C 2 Ca 2+ x2 [ ] C FW C (S)-(+)-2,2 Dimethyl-5 oxo-1,3 dioxolane-4 acetic acid, 95% [ ] C FW C C 3 (R)-( )-2,2 Dimethyl-5 oxo-1,3 dioxolane-4 acetic acid, 95% [ ] C FW C C 3 (R)-( )-2 Chloromandelic acid, [ ] C FW (S)-(+)-2 Chloromandelic acid, [ ] C FW (R)-( )-3 Chloromandelic acid, rganic Building Blocks [ ] C FW D-α-ydroxyisovaleric acid, 98.0% (T) 3C C 3 Magnesium L-lactate hydrate, 95.0% (KT, calc. based on dry substance) [ ] C 6 10 Mg 6 x 2 FW (Anh) 2 Mg 2+ x2 [ ] C FW (R)-( )-Mandelic acid, [ ] C FW C 3 3C (S)-( )-2 ydroxy-3,3 dimethylbutyric acid, [ ] C FW t-bu [ ] C FW (S)-(+)-Mandelic acid, [ ] C FW 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

42 (+)-, -Diacetyl-L-tartaric anhydride, (R)-( )-α-methoxyphenylacetic acid, (S)-( )-α-methoxy-α-(trifluoromethyl)phenylacetic acid, rganic Building Blocks [ ] C FW C (R)-( )-exahydromandelic acid, [ ] C FW (S)-(+)-exahydromandelic acid, [ ] C FW (S)-(+)-α-Methoxyphenylacetic acid [ ] C FW (S)-3 ydroxy-3 phenylpropionic acid, 98.0% (GC, sum of enantiomers) C 3 [ ] C 10 9 F 3 3 FW (R)-(+)-α-Methoxy-α-trifluoromethylphenylacetic acid, [ ] C 10 9F 3 3 FW C CF 3 3C CF3 (S)-( )-α-methoxy-α-(trifluoromethyl)phenylacetic acid, [ ] C FW [ ] C FW [ ] C 10 9F 3 3 FW C CF (S)-2 Bromo-3 phenylpropionic acid, 95.0% (T) [ ] C 9 9 Br 2 FW Br (R)-(+)-2-(4 ydroxyphenoxy)propionic acid, [ ] C FW (R)-( )-α-acetylmandelic acid, [ ] C FW C (S)-(+)-2 Phenylpropionic acid, [ ] C FW (1S,2R)-1 Methyl cis-1,2,3,6 tetrahydrophthalate, [ ] C FW (S)-(+)--Acetylmandelic acid, [ ] C FW C (R)-( )-2 Phenylpropionic acid, [ ] C FW L-( )-3 Phenyllactic acid, [1S-(1β,2α,3β)]-(+)-3 Methyl-2- (nitromethyl)-5 oxocyclopentaneacetic acid, [ ] C FW (R)-( )-Phenylsuccinic acid, 96.0% (PLC, sum of enantiomers) [ ] C FW [ ] C FW D-(+)-3 Phenyllactic acid, [ ] C FW C 3 Aluminum L-lactate, % (related on reference to anhydrous substance) [ ] C 9 15 Al 9 FW C - Al 3+ 3 (S)-(+)-Phenylsuccinic acid, 99.0% (PLC, sum of enantiomers) [ ] C FW sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

43 (S)-( )-2-(Phenylcarbamoyloxy)propionic acid, [ ] C FW (R)-( )-2 Phenylbutyric acid, [ ] C FW C (S)-(+)-2 Phenylbutyric acid, [ ] C FW C (R)-3 Phenylbutyric acid, 98.5% (GC, sum of enantiomers) [ ] C FW C 3 (S)-3 Phenylbutyric acid, 99.0% (PLC, sum of enantiomers) (S)-2 ydroxy-2 phenylbutyric acid, 96% [ ] C FW C Ph (R)-2 ydroxy-4 phenylbutyric acid, [ ] C FW (S,S)-Ethylenediamine-, -disuccinic acid trisodium salt solution [ ] C a 3 8 FW (S)-( )-Perillic acid, 95% [ ] C FW a + - 2C (1S)-(+)-Ketopinic acid, a + a+ (1R,3S)-(+)-Camphoric acid, [ ] C FW C409 C 3 3C (1S,3R)-( )-Camphoric acid, [ ] C FW (R)-(+)-Citronellic acid, [ ] C FW C (S)-( )-Citronellic acid, [ ] C FW C C 3 3C C 3 (S)-(+)-2 Methylbutyric anhydride, 94% [ ] C FW C C 3 C 3 rganic Building Blocks [ ] C FW (R)-(+)-2-(Benzyloxy)propionic acid, 97.0% (PLC) [ ] C FW C 3 [ ] C FW (1S)-( )-Camphanic acid, [ ] C FW C 3C (R)-3-(-amino)-5-hexynoic acid, [ ] C FW C (S)-3-(-amino)-5-hexynoic acid, (R)-2 ydroxy-2 phenylbutyric acid, 96% [ ] C FW C Ph (+)-trans-chrysanthemic acid, 98.0% (GC) [ ] C FW C 3C 3C C 3 [ ] C FW C (R)-3-(-amino)-5-hexenoic acid, [ ] C FW C 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

44 rganic Building Blocks (S)-3-(-amino)-5-hexenoic acid, [ ] C FW C 8 (R)-(+)--(1 Phenylethyl)succinamic acid, [ ] C FW (S)-( )--(1 Phenylethyl)succinamic acid, [ ] C FW (+)-Menthyloxyacetic acid, [ ] C FW C (R)-α-Methoxy-2 naphthylacetic acid, 99.0% [ ] C FW (S)-α-Methoxy-2 naphthylacetic acid, [ ] C FW C 3 (R)-( )-6 Methoxy-α-methyl- 2 naphthaleneacetic acid, [ ] C FW aproxen, [ ] C FW C 3C C 3 C 3 (R)-( )-α-[(3 Ethoxy-1 methyl- 3 oxo-1 propenyl)amino]benzeneacetic acid potassium salt, [ ] C K 4 FW K (S)-(+)-Z-4 Amino-2 hydroxybutyric acid, [ ] C FW Cbz (R)-(+)-3 ydroxy-5 oxo-1 cyclopentene-1 heptanoic acid, 96% [ ] C FW [1R-(2-endo,3-exo)]-3 ydroxy- 4,7,7 trimethylbicyclo[2.2.1]heptane-2 acetic acid, [ ] C FW C C 3 3C ( )-Menthyloxyacetic acid, [ ] C FW M3000 3C (R)-(+)-α-[(3 Methoxy-1 methyl- 3 oxo-1 propenyl)amino]-1,4 cyclohexadiene-1 acetic acid sodium salt, [ ] C a 4 FW (S)-(+)-Ibuprofen, [ ] C FW C 3C a C 3 (S)-2-(-amino)octanedioic acid, [ ] C FW (R)-2-(-amino)octanedioic acid, [ ] C FW (1R,2S)-( )-2 Benzamidocyclohexanecarboxylic acid, [ ] C FW (1S,2R)-(+)-2 Benzamidocyclohexanecarboxylic acid, [ ] C FW (+)-, -Di-pivaloyl-D-tartaric acid, 98.0% (T) [ ] C FW t-bu t-bu sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

45 ( )-, -Di-pivaloyl-L-tartaric acid, 98.0% (T) [ ] C FW t-bu (R)-( )-2 Fluoro-α-methyl- 4 biphenylacetic acid, [ ] C F 2 FW F t-bu C 3 (S)-( )--(1 Phenylethyl)phthalamic acid, [ ] C FW (S)-( )--[1-(1 aphthyl)ethyl]succinamic acid, [ ] C FW Rosmarinic acid, [ ] C FW ( )-mono-(1r)-menthyl phthalate, [ ] C FW C C 3 rganic Building Blocks (S)-(+)-2 Fluoro-α-methyl- 4 biphenylacetic acid, [ ] C F 2 FW F C 3 (R)-(+)--[1-(1 aphthyl)ethyl]succinamic acid, [ ] C FW Ricinoleic acid, ~80% (GC) [ ] C FW (C 2) (R)-2-[(-amino)methyl]-3- phenylpropionic acid, [ ] C FW (+)-2,3 Dibenzoyl-D-tartaric acid, [ ] C FW Ph Ph L-Lactic acid tetrabutylammonium salt solution 3C 3C C FW C 3 3C (S)-2-[(-amino)methyl]-3- phenylpropionic acid, [ ] C FW Dibenzoyl-L-tartaric acid, [ ] C FW (S)-(+)--[1-(1 aphthyl)ethyl] phthalamic acid, [ ] C FW C 3 (S)-(+)-Ketoprofen, [ ] C FW ( )-, -Dibenzoyl-L-tartaric acid monohydrate, 99.0% (T) (R)-( )--[1-(1 aphthyl)ethyl] phthalamic acid, (R)-(+)--(1 Phenylethyl)phthalamic acid, [ ] C FW [ ] C FW [ ] C FW Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 45

46 (+)-, -Di-p-toluoyl-D-tartaric acid, Di-p-toluoyl-D-tartaric acid monohydrate,,-bis[(s)-( )-1 phenylethyl] phthalamic acid, rganic Building Blocks 3C [ ] C FW ( )-, -Di-p-toluoyl-L-tartaric acid, 3C [ ] C FW C [ ] C FW ,-Bis[(R)-(+)-1 phenylethyl] phthalamic acid, [ ] C FW C C 3 C FW C sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

47 (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 [ ] i-pr i-pr i-pr C 3 (S)-( )-1-(2,4,6-Triisopropylphenyl)ethanol C [ ] References: (1) (a) de Azevedo, M. B. M.; Greene, A. E. J. rg. Chem. 1995, 60, (b) Kanazawa, A. et al. J. Chem. Soc. Perkin Trans. 1997,1911. (c) ebois, P.; Greene, A. E. J. rg. Chem. 1996, 61, (d) Ceccon, J. et al. Synlett 2005, (e) Roche, C. et al. rg. Lett. 2003, 5, (f) Muniz, M.. et al. Synlett 2005, (g) Roche, C. et al. J. rg. Chem. 2005, 70, (h) Ceccon, J. et al. rg. Lett. 2006, 8, (2) amel, M.; Grach, G.; Abrunhosa, I.; Gulea, M.; Masson, S.; Vazeux, M.; Drabowicz, J.; Mikolajczyk, M. Tetrahedron: Asymmetry 2005, 16, (3) (a) arkevitch, V. et al. Angew. Chem., Int. Ed. 2000, 39, (b) Bouchez, L. C. et al. Tetrahedron 2005, 61, (c) arkevitch, V. et al. J. rg. Chem. 2001, 66, 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

48 Cyanides/itriles rganic Building Blocks (R)-(+)-4 Chloro-3 hydroxybutyronitrile, [ ] C 4 6 FW (S)-(+)-2 Methylbutyronitrile, [ ] C 5 9 FW C (R)-(+)-4 Chloromandelonitrile, [ ] C 8 6 FW (R)-(+)-Mandelonitrile, [ ] C 8 7 FW C C C C (R)-2 Acetoxy-3,3 dimethylbutyronitrile, 99.0% (GC, sum of enantiomers) [ ] C FW C (R)-(+)-4 Methylmandelonitrile, [ ] C 9 9 FW C (R)-(+)-4 Methoxymandelonitrile, [ ] C FW C C (R)-α-Acetoxyphenylacetonitrile, 97.0% (GC, sum of enantiomers) [ ] C FW C t-bu C C C 3 tert-butyl (4R,6R)-6 cyanomethyl- 2,2 dimethyl-1,3 dioxane-4 acetate, [ ] C C FW C,-Bis(4 methoxybenzyloxy- carbonyl)-(s)-2 amino-3- (4 hydroxyphenyl)propionitrile, 96% 3C [ ] C FW C C Epoxides (S)-( )-3,3,3 Trifluoro-1,2 epoxypropane, [ ] C 3 3 F 3 FW F3C (S)-(+)-Epichlorohydrin, [ ] C 3 5 FW (S)-( )-Glycidol, [ ] C FW (R)-(+)-3,3,3 Trifluoro-1,2 epoxypropane, [ ] C 3 3 F 3 FW (R)-( )-Epichlorohydrin, [ ] C 3 5 FW F3C (R)-(+)-Propylene oxide, [ ] C 3 6 FW (S)-( )-Propylene oxide, [ ] C 3 6 FW C 3C (R)-(+)-Glycidol, [ ] C FW (R)-2 Vinyloxirane, 95.0% (GC, sum of enantiomers) [ ] C 4 6 FW C sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

49 (S)-3,4 Epoxy-1 butene, 90% (GC) [ ] C 4 6 FW Methyl (2S)-glycidate, [ ] C FW Methyl (2R)-glycidate, [ ] C FW (S)-( )-(2 Bromoethyl)oxirane, 90% (GC, sum of enantiomers) C 2 Ethyl (S)-2 oxiranylacetate, 96.0% (GC, sum of enantiomers) [ ] C FW (R)-(+)-1,2 Epoxyhexane, [ ] C 6 12 FW C 3(C 2) 2C 2 (S)-(+)-Glycidyl butyrate, [ ] C FW (R)-( )-Glycidyl butyrate, 96% (S)-2-(4 itrophenyl)oxirane, 98.0% (GC) [ ] C FW (R)-2-(4 itrophenyl)oxirane, 96.0% (GC) [ ] C FW (R)-(+)-Styrene oxide, [ ] C 8 8 FW rganic Building Blocks [ ] C 4 7 Br FW (S)-4 Chloro-1,2 epoxybutane, 98.0% (GC, sum of enantiomers) Br [ ] C FW (R)-(+)-1,2 Epoxyheptane, 97.0% (GC, sum of enantiomers) (S)-( )-Styrene oxide, [ ] C 8 8 FW [ ] C 4 7 FW (S)-( )-1,2 Epoxybutane, [ ] C 4 8 FW (R)-(+)-1,2 Epoxybutane, [ ] C 4 8 FW C 3C (R)-( )-Glycidyl methyl ether, [ ] C FW (S)-(+)-Glycidyl methyl ether, [ ] C FW C 3 [ ] C 7 14 FW (R)-(+)-3 Chlorostyrene oxide [ ] C 8 7 FW (S)-(4 Fluorophenyl)oxirane, 95.0% (GC) [ ] C 8 7 F FW (R)-(4 Fluorophenyl)oxirane, 90.0% (GC) [ ] C 8 7F FW C 2(C 2) 3C 3 F F (2R,3R)-Diethyl 2,3 epoxysuccinate, 96% [ ] C FW C C 3 (S)---2,3 epoxypropylamine, [ ] C FW (R)-(+)-1,2 Epoxyoctane, [ ] C 8 16 FW (C2)4C2 (2S,3S)-( )-3-(4 itrophenyl)glycidol, [ ] C FW Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 49

50 rganic Building Blocks (R)-( )-Glycidyl 3 nitrobenzenesulfonate, 97.0% (GC) [ ] C S FW S (S)-(+)-Glycidyl 3 nitrobenzenesulfonate, 99.0% (GC) [ ] C S FW S (1S,2S)-( )-1 Phenylpropylene oxide, [ ] C 9 10 FW C (1R,2R)-(+)-1 Phenylpropylene oxide, [ ] C 9 10 FW C (2S,3S)-( )-3 Phenylglycidol, [ ] C FW (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, [ ] C 9 11Br 3 FW [3aR-(3aα,5aβ,6aβ,6bα)]- 3a,5a,6a,6b-Tetrahydro- 2,2 dimethyloxireno[e]-1,3 benzodioxole, 96% [ ] C FW Br C 3 C 3 tert-butyldimethylsilyl (R)-( )-glycidyl ether, [ ] C Si FW C 3 t-bu Si tert-butyldimethylsilyl (S)-(+)-glycidyl ether, [ ] C Si FW C 3 t-bu Si C 3 (S)-(+)-Glycidyl benzyl ether, [ ] C FW (2S)-(+)-Glycidyl tosylate, [ ] C S FW S ( )-Limonene oxide, mixture of cis and trans, C FW C 2C (+)-Limonene oxide, mixture of cis and trans, [ ] C FW C 3C (+)-Limonene 1,2 epoxide, 97.0% (GC, sum of isomers) [ ] C FW C 2 3C 3C (R)-(+)-1,2 Epoxy-9 decene, [ ] C FW C2 C2 [ ] C FW (R)-2 xiranylanisole (R)-( )-Glycidyl benzyl ether, [ ] C FW (2R)-( )-Glycidyl 4 nitrobenzoate, [ ] C FW [ ] C FW (2R)-( )-Glycidyl tosylate, [ ] C S FW S (2S)-(+)-Glycidyl 4 nitrobenzoate, [ ] C FW sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

51 (2S)-(+)-2 Methylglycidyl 4 nitrobenzoate, [ ] C FW (2R)-( )-2 Methylglycidyl 4 nitrobenzoate, [ ] C FW (2S,3S)-trans-3 Methyloxirane- 2 methyl 4 nitrobenzoate, 97.0% (PLC, sum of enantiomers) [ ] C FW C 2 (R)-(+)-1,2 Epoxydodecane, [ ] C FW C 2(C 2) 8C 3 (R)-(+)-1,2 Epoxytridecane, [ ] C FW C2(C2)9 (2 S,3 S)-4 -Bromo-cis-2,3 -epoxybutyl (1S)-10 camphorsulfonate, [ ] C Br 5 S FW Br 3C S (R)-(+)-1,2 Epoxytetradecane, (2R,3S)-(+)-3-(Benzyloxymethyl)oxirane-2 methanol 4 nitrobenzoic acid ester, 99.0% (PLC, sum of enantiomers) [ ] C FW (2S,3R)-( )-3-(Benzyloxymethyl)oxirane-2 methanol 4 nitrobenzoic acid ester, 99.0% (PLC, sum of enantiomers) [ ] C FW rganic Building Blocks (R)-( )--(2,3 Epoxypropyl)phthalimide, 99.0% (GC) [ ] C FW (S)-(+)--(2,3 Epoxypropyl)phthalimide, 99.0% (GC) [ ] C FW (2R)-(+)-3,3 Dimethylglycidyl 4 nitrobenzoate, [ ] C FW C2(C2)10 (2S,3S)-1,2 Epoxy-3-(-amino)- 4 phenylbutane, [ ] C FW (R)-(+)-1,2 Epoxypentadecane, [ ] C FW C2(C2)11 (R)-(+)-Glycidyl trityl ether, [ ] C FW (S)-( )-Glycidyl trityl ether, [ ] C FW [ ] C FW C 3 C Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 51

52 Esters (+)-Methyl (R)-2 chloropropionate, Methyl (S)-(+)-3 hydroxybutyrate, Ethyl (R)-(+)-4,4,4 trifluoro- 3 hydroxybutyrate, rganic Building Blocks [ ] C FW C ( )-Methyl (S)-2 chloropropionate, [ ] C FW ( )-Methyl L-lactate, [ ] C FW (+)-Methyl D-lactate, [ ] C FW C 3C C 3 ( )-Methyl (S)-3 bromo-2 methylpropionate, [ ] C 5 9Br 2 FW Br [ ] C FW C Methyl (R)-( )-3 hydroxy-2 methylpropionate, [ ] C FW C 3 Methyl (S)-(+)-3 hydroxy-2 methylpropionate, [ ] C FW ( )-Ethyl L-lactate, [ ] C FW E34102 C 3 C 3 3C (+)-Ethyl D-lactate, 99.0% (GC, sum of enantiomers) [ ] C FW C C 3 C 3 [ ] C 6 9 F 3 3 FW F3C Ethyl (R)-2-(trifluoromethylsulfonyloxy)propionate, 97.0% ( 19 F -MR) [ ] C 6 9F 3 5S FW F3C S Ethyl (S)-2-(trifluoromethylsulfonyloxy)propionate, 96% [ ] C 6 9F 3 5S FW F3C S (R)-(+)-2 Methylsuccinic acid 4 methyl ester, 95% [ ] C FW Dimethyl (S)-( )-malate, [ ] C FW C C 3 3C C 3 Methyl (R)-(+)-3 bromo-2 methylpropionate, [ ] C 5 9 Br 2 FW Methyl (R)-3 hydroxybutyrate, [ ] C FW Br 3C C 3 Dimethyl (4R,5R)-1,3,2 dioxathiolane-4,5 dicarboxylate 2,2 dioxide, [ ] C S FW C C 3 S Dimethyl (4S,5S)-1,3,2 dioxathiolane-4,5 dicarboxylate 2,2 dioxide [ ] C S FW C S Dimethyl (R)-(+)-malate, [ ] C FW C ( )-Dimethyl D-tartrate, [ ] C FW C sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

53 (+)-Dimethyl L-tartrate, [ ] C FW C Ethyl (R)-(+)-4 bromo-3 hydroxybutyrate [ ] C 6 11 Br 3 FW Br Ethyl (S)-( )-4 bromo-3 hydroxybutyrate [ ] C 6 11 Br 3 FW Br Ethyl (R)-(+)-4 chloro-3 hydroxybutyrate, 96% [ ] C FW (+)-Methyl (S)-3 hydroxyvalerate, 98.0% (GC, sum of enantiomers) [ ] C FW C ( )-Isopropyl L-lactate, 97.0% (GC, sum of enantiomers) [ ] C FW C Ethyl (R)-( )-4 cyano-3 hydroxybutyrate, 95% [ ] C FW C C 3 C 3 C 3 Dimethyl (R)-(+)-methylsuccinate, [ ] C FW C C 3 C 3 Butyl (S)-( )-lactate, [ ] C FW C Isobutyl (R)-(+)-lactate, [ ] C FW C (+)-tert-butyl D-lactate, 99.0% (GC, sum of enantiomers) [ ] C FW C 3 C 3 3C C 3 C 3 ( )-Butyl L-lactate, 97.0% (GC, sum of enantiomers) [ ] C FW C rganic Building Blocks Ethyl (S)-( )-4 chloro-3 hydroxybutyrate, 96% [ ] C FW Ethyl (R)-( )-3 hydroxybutyrate, [ ] C FW C Ethyl (S)-3 hydroxybutyrate, [ ] C FW C ( )-Methyl (R)-3 hydroxyvalerate, 98.0% (GC, sum of enantiomers) [ ] C FW C Methyl (R)-(+)-2,2 dimethyl-1,3 dioxolane-4 carboxylate, [ ] C FW C C 3 C 3 ( )-Methyl (S)-2,2 dimethyl-1,3 dioxolane-4 carboxylate, 96% [ ] C FW C Isobutyl (S)-2 chloropropionate, 99.0% (GC, sum of enantiomers) [ ] C FW C C 3 Ethyl (1R,2S)-cis-2 hydroxycyclopentanecarboxylate, 97.0% (GC) [ ] C FW Ethyl (1S,2S)-trans-2 hydroxycyclopentanecarboxylate, 97.0% (GC, sum of enantiomers) [ ] C FW Methyl (4S)-(+)-2,2 dimethyl- 1,3 dioxolane-4 acetate, [ ] C FW C Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 53

54 rganic Building Blocks (+)-Diethyl L-tartrate, [ ] C FW C ( )-Diethyl D-tartrate, [ ] C FW C C 3 C 3 tert-butyl (R)-2 hydroxybutyrate, [ ] C FW C ( )-tert-butyl (S)-2 hydroxybutyrate, [ ] C FW C C 3 C 3 C 3 Methyl (S)-(+)-3-(2,2 dimethyl- 1,3 dioxolan-4 yl)-cis-2 propenoate, 85% [ ] C FW C C 3 ( )-Dimethyl 2,3--isopropylidene- L-tartrate, [ ] C C FW C (+)-Dimethyl 2,3--isopropylidene- D-tartrate, [ ] C C FW C Ethyl (1R,2S)-cis-2 hydroxycyclohexanecarboxylate, 97.0% (GC) Benzyl (S)-( )-lactate, 90% [ ] C FW C Methyl L-3 phenyllactate, 97.0% (PLC) [ ] C FW Methyl (2R,3S)-(+)-2,3 dihydroxy- 3 phenylpropionate, [ ] C FW Methyl (2S,3R)-( )-2,3 dihydroxy- 3 phenylpropionate, [ ] C FW C 3 (+)-tert-butyl (S)-3 hydroxybutyrate, 96.0% (GC) [ ] C FW C Methyl (R)-( )-mandelate, [ ] C FW Methyl (S)-(+)-mandelate, [ ] C FW Methyl (S)-(+)-3-(2,2 dimethyl- 1,3 dioxolan-4 yl)-trans-2 propenoate, 93% [ ] C FW [ ] C FW Ethyl (1S,2S)-trans-2 hydroxycyclohexanecarboxylate, 95.0% (GC) [ ] C FW Ethyl (R)-( )-mandelate, [ ] C FW Ethyl (S)-(+)-mandelate, [ ] C FW C Methyl (R)-(+)-2-(4 hydroxyphenoxy)propionate, [ ] C FW Ethyl (R)-cis-3-(2,2 dimethyl-1,3 dioxolan-4 yl)propenoate, 98.0% (GC, sum of enantiomers) [ ] C FW C C 3 Ethyl (R)-( )-3-(2,2 dimethyl-1,3 dioxolan-4 yl)-trans-2 propenoate, [ ] C FW C 3C sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

55 Ethyl (S)-(+)-3-(2,2 dimethyl-1,3 dioxolan-4 yl)-2 propenoate,predominantly trans, [ ] C FW C C 3 Diisopropyl (S)-( )-malate, [ ] C FW C C 3 ( )-Diisopropyl D-tartrate, [ ] C FW C C 3 (+)-Diisopropyl L-tartrate, [ ] C FW C 3 C 3 C 3 C 3 3C Methyl (R)-3 phenylbutyrate, 99.0% (GC, sum of enantiomers) [ ] C FW (+)-Ethyl (R)-3 hydroxy-3 phenylpropionate, 99.0% (GC, sum of enantiomers) (+)-Methyl (R)-3-(1 methyl-2 oxocyclohexyl)propionate, [ ] C FW Ethyl (S)-( )-2-(tert-butyldimethylsilyloxy)propionate, [ ] C Si FW t-bu Si Methyl (S)-( )-4-(tert-butyldimethylsilyloxy)-2 hydroxybutanoate [ ] C Si FW Si t-bu Ethyl (R)-( )-2 hydroxy-4 phenylbutyrate, [ ] C FW (5R,6R)-Dimethyl 5,6 dimethoxy- 5,6 dimethyl-1,4 diox-2 ene- 2,3 dicarboxylate, C FW C 3C C 3 C 3 Ethyl (R)-nipecotate, L-tartrate, [ ] C FW C 3 (1R)-( )-eomenthyl acetate, [ ] C FW C C 3 (1S)-(+)-eomenthyl acetate, [ ] C FW C (1R)-( )-Menthyl acetate, [ ] C FW C C 3 (1S)-(+)-Menthyl acetate, [ ] C FW C C 3 C 3 C 3 C 3 rganic Building Blocks [ ] C FW ( )-Ethyl (S)-3 hydroxy-3 phenylpropionate, 97.0% (GC, sum of enantiomers) [ ] C FW (2R,3R,5R,6R)-Dimethoxy-5,6 dimethyl-1,4 dioxane-2,3 dicarboxylic acid dimethyl ester, [ ] C FW C 3C C (+)-Ethyl (S)-2 hydroxy-4 cyclohexylbutyrate, 99.0% (GC, sum of enantiomers) C FW ( )-Di-tert-butyl D-tartrate, C [ ] C FW 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

56 rganic Building Blocks (+)-Di-tert-butyl L-tartrate, [ ] C FW C C 3 tert-butyl (S)-2 hydroxyoctanoate, 97.0% (GC) C FW C C 3 C 3 (+)-Dimethyl 2,3--benzylidene-Dtartrate, 98.0% (GC, sum of enantiomers) [ ] C FW C 3 (R)-( )-1 Phenylethyl 3,5 dinitrobenzoate, [ ] C FW (S)-(+)-1 Phenylethyl 3,5 dinitrobenzoate, [ ] C FW Benzyl (R)-( )-mandelate, [ ] C FW ( )-Dibenzyl D-tartrate, 98.0% (PLC, sum of enantiomers) [ ] C FW (1R,2S,5R)-(+)-5 Methyl-2-(1 methyl-1 phenylethyl)cyclohexyl chloroacetate, [ ] C FW C C 3 (R)-(+)-1,1,2 Triphenyl-1,2 ethanediol 2 acetate, [ ] C FW C C 3 Methyl (R)-(+)-3 hydroxy-5 oxo- 1 cyclopentene-1 heptanoate, [ ] C FW Methyl (S)-( )-3 hydroxy-5 oxo- 1 cyclopentene-1 heptanoate, [ ] C FW ( )-Bis[(S)-1-(ethoxycarbonyl)ethyl] fumarate, Benzyl (S)-(+)-mandelate, [ ] C FW Benzyl (R)-(+)-2 hydroxy-3 phenylpropionate, [ ] C FW Benzyl (S)-( )-2 hydroxy-3 phenylpropionate, [ ] C FW ( )-Dimenthyl fumarate, 95% [ ] C FW C 3C (1S)-(+)-Dimenthyl succinate, [ ] C FW C 3C 3C [ ] C FW C (+)-Diisopropyl-, -bis(trimethylsilyl)-l-tartrate, [ ] C Si 2 FW C 3 3C Si C 3 C 3 3C C 3 3C Si C 3 C 3 (1R)-( )-Dimenthyl succinate, 3C [ ] C FW C sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

57 ydrocarbons (S)-(+)-1 Bromo-2 methylbutane, [ ] C 5 11 Br FW C (S)-(+)-1 Iodo-2 methylbutane, [ ] C 5 11I FW C Br I (+)-Cuparene, 99.0% (GC, sum of enantiomers) [ ] C FW C (+)-α-pinene, [ ] C FW ( )-α-pinene, [ ] C FW ( )-β-pinene, [ ] C FW C 3C C 3 3C 3C 3C C 3 C 2 (+)-Camphene, 80% [ ] C FW C301 3C C2 C 3 ( )-Camphene, 75% (90% as camphene and fenchene) [ ] C FW C 3C (1R)-(+)-trans-Isolimonene, 95.0% (GC, sum of enantiomers) [ ] C FW C C 3 rganic Building Blocks (S)-(+)-Citronellyl bromide, 95% [ ] C Br FW C (R)-( )-Citronellyl bromide, [ ] C Br FW C ( )-Menthyl chloride, [ ] C FW C C 3 (R)-( )-α-phellandrene, 95.0% (GC, sum of enantiomers) [ ] C FW C C 3 Br Br C 3 (1S)-(+)-3 Carene, [ ] C FW (+)-2 Carene, [ ] C FW C 3C 3C 3C (1S,3R)-cis-4 Carene, 97.0% (GC, sum of enantiomers) [ ] C FW C (1S,3S)-trans-4 Carene, 85% (GC, sum of enantiomers) [ ] C FW C C 3 C (S)-( )-Limonene, 96% [ ] C FW C ( )-β-citronellene, 90% (GC, sum of enantiomers) [ ] C FW (+)-Cyclosativene, [ ] C FW C C 2 C 3 C 3 3C 3C C 3 C Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 57

58 rganic Building Blocks ( )-Isosativene, 97.0% (GC, sum of enantiomers) [ ] C FW (+)-Valencene, 70% [ ] C FW C 3C C 3 C 3 C 2 ( )-β-chamigrene, ~90% (GC, sum of enantiomers) [ ] C FW (3aS,6aS)-3,6-Diphenyl- 1,3a,4,6a-tetrahydropentalene, [ ] C FW C2 3C C 3 8 (3aR,6aR)-3,6-Diphenyl- 1,3a,4,6a-tetrahydropentalene, [ ] C FW Isocyanates/Isocyanides Methyl (S)-( )-2 isocyanato- 3 methylbutyrate, (S)-( )-α-methylbenzyl isocyanate, (R)-( )-1-(1 aphthyl)ethyl isocyanate, [ ] C FW C C [ ] C 9 9 FW C C 3 [ ] C FW C C (S)-( )-α-methylbenzyl isocyanide, 96% [ ] C 9 9 FW C Methyl (R)-(+)-2 isocyanato- 3 phenylpropionate, [ ] C FW C (S)-(+)-1-(1 aphthyl)ethyl isocyanate, [ ] C FW C C (R)-(+)-α-Methylbenzyl isocyanate, Methyl (S)-( )-2 isocyanato- 3 phenylpropionate, [ ] C 9 9 FW C [ ] C FW C 3 C sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

59 Ketones (R)-(+)-3 Methylcyclopentanone, [ ] C 6 10 FW M39709 (R)-5 ydroxy-2 hexanone, 90% (GC, sum of enantiomers) [ ] C FW C (1R,5S)-(+)-cis-Bicyclo[3.2.0]hept- 2 en-6 one, 98.0% (GC, sum of enantiomers) [ ] C 7 8 FW ( )-(1S,5R)-cis-Bicyclo[3.2.0]hept- 2 en-6 one, 98.0% (GC, sum of enantiomers) [ ] C 7 8 FW C 3 (1R)-(+)-opinone, [ ] C 9 14 FW C (S)-(+)-2,3,7,7a-Tetrahydro-7amethyl-1-indene-1,5(6)-dione, [ ] C FW (+)-3,9 Dibromocamphor, [ ] C Br 2 FW (R)-( )-Carvone, [ ] C FW (S)-(+)-Carvone, 96% 2C Br 3C 3C Br C 3 (1R)-( )-Camphorquinone, [ ] C FW C 3C (1S)-(+)-Camphorquinone, [ ] C FW C (3aS,7aS)-(+)-exahydro-3a-hydroxy-7a-methyl-1,5 indandione, [ ] C FW C (+)-3 Bromocamphor, 97.0% (GC, sum of enantiomers) [ ] C 10 15Br FW C 3C Br rganic Building Blocks (R)-(+)-3 Methylcyclohexanone, [ ] C 7 12 FW M38583 C 3 [ ] C FW (1S)-( )-Verbenone, 94% [ ] C FW C 3 2C C 3 C 3 3C 3C (R)-(+)-Pulegone, [ ] C FW (S)-( )-Pulegone, [ ] C FW C C 3 C 3 3C C Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 59

60 rganic Building Blocks ( )-Pulegone, 98.0% (GC, sum of enantiomers) [ ] C FW (+)-Dihydrocarvone [ ] C FW C 3C (+)-Fenchone, 98.0% (GC, sum of enantiomers) [ ] C FW (1R)-( )-Fenchone, [ ] C FW α,β-thujone [ ] C FW C 3C C 3 C 3 (1S)-( )-Camphor, [ ] C FW (S)-(+)-5-(1 ydroxy-1 methyl- ethyl)-2 methyl-2 cyclohexen- 1 one, [ ] C FW C 3C 3C C 3 (1R,2R,5R)-(+)-2 ydroxy-3 pinanone, [ ] C FW C (1S,2S,5S)-( )-2 ydroxy-3 pinanone, [ ] C FW ( )-Menthone, 90% [ ] C FW C C 3 3C C 3 (R)-( )-8a-Methyl-3,4,8,8a-tetrahydro-1,6(2,7)-naphthalenedione, 98.0% (GC, sum of enantiomers) [ ] C FW C (R)-( )-4,4a,5,6,7,8 exahydro-4amethyl-2(3)-naphthalenone, 98.0% (GC, sum of enantiomers) [ ] C FW ( )-3-(Trifluoroacetyl)camphor, [ ] C F 3 2 FW C (+)-3-(Trifluoroacetyl)camphor, [ ] C 12 15F 3 2 FW (S)-(+)-Benzoin, 3C 3C CF3 CF ( )-α-thujone, 96.0% (GC) [ ] C FW (1R)-(+)-Camphor, [ ] C FW C 3C 3C (S)-(+)-3,4,8,8a-Tetrahydro-8amethyl-1,6(2,7)-naphthalenedione, [ ] C FW C [ ] C FW (R)-( )-Benzoin, [ ] C FW sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

61 3-(Perfluorobutyryl)-( )-camphor, [ ] C F 7 2 FW C F F CF3 F F 3-(Perfluorobutyryl)-(+)-camphor, 96% [ ] C 14 15F 7 2 FW C 3C F F CF3 F F Irone, 90% (GC) [ ] C FW C 3C 5-[3,4-(Dimethoxy)phenyl]- 1,3 cyclohexanedione, [ ] C FW C 3C C 3 C 3 ( )-Isolongifolen-9 one, 99.5% (GC, sum of enantiomers) [ ] C FW C 3C 7 Acetyl-5,8 dihydroxy-4 isopropyl-1 methylbicyclo[4.3.0]nonane, [ ] C FW C C 3 C 3 rganic Building Blocks (+)-ootkatone, 99.0% (GC) [ ] C FW C 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

62 Lactams/Lactones rganic Building Blocks (R)-4-(Trichloromethyl)-2 oxetanone, 99.0% (GC) [ ] C FW C (S)-( )-4 xo-2 azetidinecarboxylic acid, [ ] C FW (R)-(+)-α-ydroxy-γ-butyrolactone, [ ] C FW (S)-( )-α-ydroxy-γ-butyrolactone, [ ] C FW (S)-β-ydroxy-γ-butyrolactone, 96% [ ] C FW (S)-( )-α-amino-γ-butyrolactone hydrobromide, [ ] C Br FW (R)-(+)-4 Methyl-4-(trichloromethyl)-2 oxetanone, 2 Br (S)-( )-4 Methyl-4-(trichloromethyl)-2 oxetanone, [ ] C FW C 3C (R)-γ-Valerolactone, 97.0% (GC) [ ] C FW C (1S)-(+)-2 Azabicyclo[2.2.1]hept- 5 en-3 one, [ ] C 6 7 FW (1R)-( )-2 Azabicyclo[2.2.1]hept- 5 en-3 one, [ ] C 6 7 FW (3S)-cis-3,6 Dimethyl-1,4 dioxane- 2,5 dione, [ ] C FW C C 3 (R)-5 exanolide, 95.0% (GC, sum of enantiomers) [ ] C FW D-( )-Pantolactone, [ ] C C 3C 3C (S)-(+)-Pantolactone, [ ] 3C C C FW L-( )-α-amino-ε-caprolactam hydrochloride, 97.0% (AT) [ ] C FW (1S,5R)-2 xabicyclo[3.3.0]oct- 6 en-3 one, [ ] C FW (1R,5S)-3 xabicyclo[3.3.0]oct- 6 en-2 one, 95.0% (GC) [ ] C FW (R)-( )-γ-ethoxycarbonyl-γ-butyrolactone, 95% [ ] C FW C 3 (3aR,4S,5R,6aS)-( )-exahydro- 5 hydroxy-4-(hydroxymethyl)-2cyclopenta[b]furan-2 one, [ ] C FW [ ] C FW C 3C FW sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

63 (3aS,4R,5S,6aR)-(+)-exahydro- 5 hydroxy-4-(hydroxymethyl)-2cyclopenta[b]furan-2 one, [ ] C FW (R)-α-Acryloyloxy-β,β-dimethyl-γbutyrolactone, 95% [ ] 3C C C FW C2 (+)-2,3 Cyclohexylidene-L-erythruronic acid, 96% [ ] C FW Benzyl (S)-( )-4 oxo-2 azetidinecarboxylate, [ ] C FW (+)-Corey lactone, 4 phenylbenzoate alcohol, [ ] C FW ( )-Corey lactone, 4 phenylbenzoate alcohol, [ ] C FW rganic Building Blocks (R)-2-tert-Butyl-6 methyl-1,3 dioxin-4 one, 99.0% (PLC, sum of enantiomers) [ ] C FW C t-bu (R)-( )-Dihydro-5-(p-tolylsulfonyloxymethyl)-2(3)-furanone, [ ] C S FW S (S)-(+)-γ-Trityloxymethyl-γ-butyrolactone, [ ] C FW (2R,6R)-2-tert-Butyl-6 methyl- 1,3 dioxan-4 one, 98.5% (GC, sum of enantiomers) [ ] C FW C (1R)-(+)-Camphanic acid, [ ] C FW t-bu 3C C 3 C 3 (S)-(+)-Dihydro-5-(p-tolylsulfonyloxymethyl)-2(3)-furanone, [ ] C S FW S [3R(1 R,4R)]-(+)-4 Acetoxy-3-[1- (tert-butyldimethylsilyloxy)ethyl]- 2 azetidinone, [ ] C Si FW C 3C C 3 C 3 Si t-bu C (R)-( )-γ-trityloxymethyl-γ-butyrolactone, [ ] C FW Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 63

64 Polyamines (R)-(+)-1,2 Diaminopropane dihydrochloride, (1R,2R)-( )-1,2 Diaminocyclohexane, (1R,2R)-(+)-1,2 Diaminocyclohexane L-tartrate, rganic Building Blocks [ ] C FW C (S)-( )-1,2 Diaminopropane dihydrochloride, [ ] C FW C [ ] C FW (1S,2S)-(+)-1,2 Diaminocyclohexane, [ ] C FW [ ] C FW (1S,2S)-( )-1,2 Diaminocyclohexane D-tartrate, [ ] C FW (R)-(+)-Propylenediamine dihydrochloride, 98.0% (TLC/AT) [ ] C FW C (R,R)-( )-, -Dimethyl-1,2 cyclohexanediamine, 97.0% (GC) [ ] C FW (1R,2R)-(+)-1,2 Diphenylethylenediamine, [ ] C FW (1S,2S)-trans-1,2 Cyclopentanediamine dihydrochloride, [ ] C FW (S,S)-(+)-, -Dimethyl-1,2 cyclohexanediamine, 97.0% (GC) [ ] C FW C (1S,2S)-( )-1,2 Diphenylethylenediamine, [ ] C FW (1R,2R)-trans-1,2 Cyclopentanediamine dihydrochloride, C FW sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

65 Polyols (R)-( )-3 Chloro-1,2 propanediol, [ ] C FW (S)-(+)-3 Chloro-1,2 propanediol, [ ] C FW (2R,3R)-( )-2,3 Butanediol, [ ] C FW C (R)-(+)-1,2,4 Butanetriol, [ ] C FW (S)-( )-1,2,4 Butanetriol, C 3 (S)-2 Methyl-1,4 butanediol, 97.0% (GC, sum of enantiomers) [ ] C FW (1S-cis)-3 Bromo-3,5 cyclohexadiene-1,2 diol, 96% [ ] C 6 7Br 2 FW Br rganic Building Blocks (R)-( )-1,2 Propanediol, 96% [ ] C FW (S)-(+)-1,2 Propanediol, 96% [ ] C FW C 3C (S)-3 Butene-1,2 diol, 97.0% (GC) [ ] C FW (R)-( )-1,3 Butanediol, [ ] C FW C 3C [ ] C FW (1R,2R)-(-)-trans-1,2 Cyclopentanediol, [ ] C FW (1S,2S)-(+)-trans-1,2 Cyclopentanediol, [ ] C FW (R,R)-( )-2,4 Pentanediol, [ ] C FW C (1S,2S)-trans-1,2 Cyclohexanediol, [ ] C FW (1R,2R)-trans-1,2 Cyclohexanediol, [ ] C FW (2S,5S)-2,5 exanediol, [ ] C FW C (2R,5R)-2,5 exanediol, 99.0% (GC, sum of enantiomers) C 3 (S)-(+)-1,3 Butanediol, [ ] C FW C (2S,3S)-(+)-2,3 Butanediol, [ ] C FW C (2S,4S)-(+)-Pentanediol, [ ] C FW C (R)-2 Methyl-1,4 butanediol, 98.0% (GC, sum of enantiomers) [ ] C FW [ ] C FW C (R)-( )-2 Methyl-2,4 pentanediol, [ ] C FW C 3 3C 3C Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 65

66 rganic Building Blocks (R)-(+)-3,3 Difluoro-1,2 heptanediol, 95% [ ] C 7 14 F 2 2 FW D-Pinitol, 95% [ ] C FW F F (2R,6R)-2,6 eptanediol, 99.0% (GC, sum of enantiomers) [ ] C FW (S)-(+)-1-(2 Chlorophenyl)- 1,2 ethanediol, 96% [ ] C FW C 3 3C C 3 (R)-( )-1 Phenyl-1,2 ethanediol, [ ] C FW (S)-(+)-1 Phenyl-1,2 ethanediol, [ ] C FW (3R,6R)-3,6 ctanediol, 98.0% (GC, sum of enantiomers) [ ] C FW C (R)-(+)-1 Phenyl-1,3 propanediol, 99.0% (GC, sum of enantiomers) [ ] C FW [3aS-(3aα,4α,5α,7aα)]-7 Bromo- 3a,4,5,7a-tetrahydro-2,2 dimethyl- 1,3 benzodioxole-4,5 diol, [ ] C 9 13 Br 4 FW Br [3aS-(3aα,4α,5α,7aα)]-3a,4,5,7a- Tetrahydro-2,2 dimethyl- 1,3 benzodioxole-4,5 diol, [ ] C FW (R)-( )-1,3 onanediol, [ ] C FW (C2)4C2 (1R,2S)-cis-1,2 Dihydro-1,2 naphthalenediol, 98.0% (GC) [ ] C FW C 3 (1R,2R,3S,5R)-( )-Pinanediol, [ ] C FW C C 3 (1S,2S,3R,5S)-(+)-Pinanediol, [ ] C FW C C 3 3C (R)-(+)-1,2 Decanediol, [ ] C FW (C2)6C2 (S)-( )-1,2 Decanediol, [ ] C FW (C2)6C2 [ ] C FW C (3S,6S)-2,7 Dimethyl-3,6 octanediol, 99.0% (GC, sum of enantiomers) (2R,3R)-( )-2 Benzyloxy- 1,3,4 butanetriol [ ] C FW C 3 (R)-( )-1-(2 aphthyl)-1,2 ethanediol, [ ] C FW (S)-(+)-1-(2 aphthyl)-1,2 ethanediol, [ ] C FW (1S-cis)-3 Phenyl-3,5 cyclohexadiene-1,2 diol, [ ] C FW sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

67 (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, [ ] C FW (S,S)-(+)-1 Phenylcyclohexane-cis- 1,2 diol, [ ] C FW [ ] C FW (S)-( )-1,1 Diphenyl-1,2 propanediol, [ ] C FW C [ ] C FW (S,S)-( )-1,2 Di(1 naphthyl)- 1,2 ethanediol, [ ] C FW rganic Building Blocks (R)-(+)-1,2 Dodecanediol, [ ] C FW (C2)8C2 (S)-( )-1,2 Dodecanediol, [ ] C FW (C2)8C2 (S,S)-( )-ydrobenzoin, [ ] C FW (S)-( )-1,1,2 Triphenyl-1,2 ethanediol, [ ] C FW Sclareol [ ] C FW C 3C C 3 (R,R)-(+)-1,2 Di(1 naphthyl)- 1,2 ethanediol, C2 [ ] C FW (+)-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 [ ] C FW (R,R)-(+)-ydrobenzoin, [ ] C FW [ ] C FW C Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 67

68 Protected Alcohols/Amines rganic Building Blocks (R)-(+)-4-(Chloromethyl)-2,2 dimethyl-1,3 dioxolane, [ ] C FW (S)-( )-4-(Chloromethyl)-2,2 dimethyl-1,3 dioxolane, [ ] C FW C C 3 3C C 3 ( )-Dihydrocarvyl acetate, 95% [ ] C FW C C 3 (R)-(+)-4 exyl-2,2 dimethyl-1,3 dioxane, [ ] C FW (C2)4C2 (1R,2R)-( )--p-tosyl-1,2 cyclohexanediamine, C S FW S 2 (1S,2S)-(+)--p-Tosyl-1,2 cyclohexanediamine, C S FW S C (R)-5 Acetoxy-1 chlorohexane, (S)-4 Benzyloxymethyl-2,2 dimethyl-1,3 dioxolane, 95.0% (GC, sum of enantiomers) (S)-( )-1,2 Propanediol di-p-tosylate, [ ] C FW C 3C (1R,2R)-trans---1,2 cyclohexanediamine, [ ] C FW (1S,2S)-trans---1,2 cyclohexanediamine, [ ] C FW ( )-Bornyl acetate, 95% 2 2 [ ] C FW C (R)-( )-2,2 Dimethyl-1,3 dioxolan- 4 ylmethyl p-toluenesulfonate, [ ] C S FW C S (S)-(+)-2,2 Dimethyl-1,3 dioxolan- 4 ylmethyl p-toluenesulfonate, [ ] C S FW C C 3 S C 3 3C [ ] C S 2 FW S S C 3 ( )-2,3 Butanediyl di(p-toluenesulfonate), 3C [ ] C S 2 FW S S C 3 (1R,2R)-(+)-, -Di-p-tosyl- 1,2 cyclohexanediamine, [ ] C FW C C S S B C [ ] C S 2 FW sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

69 (1S,2S)-( )-, -Di-p-tosyl- 1,2 cyclohexanediamine, (1R,2R)-( )--p-tosyl-1,2 diphenylethylenediamine, (1S,2S)-(+)--p-Tosyl-1,2 diphenylethylenediamine, 3C [ ] C S 2 FW S S Sulfonamides/Sulfinamides (R)-( )-p-toluenesulfinamide, [ ] C 7 9S FW C S (S)-(+)-p-Toluenesulfinamide, [ ] C 7 9S FW C S (1R)-trans-, -1,2 Cyclohexanediylbis(1,1,1 trifluoromethanesulfonamide), [ ] C 8 12F 6 2 4S 2 FW CF 3 S S CF 3 [ ] C S FW S (S)-( )--[1-(ydroxymethyl)- 2 phenylethyl]-4 methylbenzenesulfonamide, [ ] C S FW C S (R,R)-(+)-, -Bis(α-methylbenzyl) sulfamide, [ ] C S FW C 3 S (S,S)-( )-, -Bis(α-methylbenzyl) sulfamide, [ ] C S FW C 3 S C 3 C 3 [ ] C S FW S C 3 ( )-10 Dicyclohexylsulfamoyl-D-isoborneol, [ ] C S FW C S (+)-,-Dicyclohexyl-(1R)-isoborneol-10 sulfonamide, [ ] C S FW C 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% [ ] C S FW S 3C (1R)-10 Camphorsulfonamide, (S)--( )-p-tolylsulfinyltryptamine, [ ] C S FW S C 3 [ ] C S FW C 3C S [ ] C S FW C S Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 69

70 Sulfonates/Sulfinates (S)-(+)-2 Methylbutyl methanesulfonate, (1R)-( )-10 Camphorsulfonic acid, (1R,2S,5R)-( )-Menthyl (S)-p-toluenesulfinate, rganic Building Blocks [ ] C S FW C (2R,3R)-Butanediol bis(methanesulfonate), C S 2 FW S 3C S S [(1R)-(endo,anti)]-(+)-3 Bromocamphor-8 sulfonic acid ammonium salt, [ ] C S FW C C 3 S 3 (1S)-(+)-10 Camphorsulfonic acid, [ ] C S FW C2107 3C S (1R)-( )-10 Camphorsulfonic acid ammonium salt [ ] C S FW C S 3C (1S,2R,5S)-(+)-Menthyl (R)-p-toluenesulfinate, [ ] C S FW C S C 3 3C C 3 [ ] C Br 4 S 3 FW S 3C Br [ ] C S FW C S + 4 B (1S)-(+)-3 Bromocamphor-10 sulfonic acid hydrate, (S)-(+)-1 Methylpropyl 4 methylbenzenesulfonate, 95% [ ] C Br 4 S x 2 FW (Anh) 3C S C 3 Br x 2 [ ] C S FW C S thers (R)-( )-1 Aminoethylphosphonic acid [ ] C P FW A C (S)-(+)-1 Aminoethylphosphonic acid, [ ] C P FW C P P (1S)-(+)-(1 Aminopropyl)phosphonic acid, [ ] C P FW C 2 P (R)-(+)-Propylene carbonate, [ ] C FW C 3 (S)-( )-Propylene carbonate, [ ] C FW (1R)-(+)-(1 Amino-2 methylpropyl) phosphonic acid, [ ] C P FW C 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.

71 (1S)-( )-(1 Amino-2 methylpropyl) phosphonic acid, (R)--(α-Methylbenzyl)hydroxylamine oxalate salt, 96% (1R,E)-(+)-Camphorquinone 3 oxime, [ ] C P FW C 2 P (S)-( )-2 ydroxy--methylsuccinimide, [ ] C FW (R)-(+)-4-(Methoxymethyl)-1,3 dioxolan-2 one, [ ] C FW (S)-( )-4-(Methoxymethyl)-1,3 dioxolan-2 one, [ ] C FW (S)-( )-3 Acetylthio-2 methylpropanoic acid, [ ] C S FW C (R)-(+)-Methyl p-tolyl sulfoxide, [ ] C 8 10 S FW C (S)-( )-Methyl p-tolyl sulfoxide, [ ] C 8 10S FW C S C 3 C 3 C 3 S S [ ] C 8 11 C FW (S)--(α-Methylbenzyl)hydroxylamine oxalate salt, 96.0% [ ] C 8 11 C FW (S)-( )-1,2 Epithiooctane, 90% [ ] C 8 16 S FW 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, [ ] C 9 12Br 3 3 FW (1R)-( )-10 Camphorsulfonyl chloride, [ ] C S FW (1S)-(+)-10 Camphorsulfonyl chloride, [ ] C S FW Br 3C 3C S 3C S (1S,E)-( )-Camphorquinone 3 oxime, [ ] C FW C C 3 C 3 [ ] C FW C C 3 (1S)-( )-Camphorsulfonylimine, [ ] C S FW C (1R)-(+)-Camphorsulfonylimine, [ ] C S FW C C 3 S S (1R)-Camphor oxime, 97.0% (GC, sum of enantiomers) [ ] C FW C 3C (R)-(+)-4-(2 Chlorophenyl)-2 hy- droxy-5,5 dimethyl- 1,3,2 dioxaphosphorinane 2 oxide, [ ] C P FW P C 3 C 3 (S)-( )-4-(2 Chlorophenyl)-2 hy- droxy-5,5 dimethyl- 1,3,2 dioxaphosphorinane 2 oxide, [ ] C P FW P C 3 rganic Building Blocks Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com. 71

72 (4R)-2 ydroxy-5,5 dimethyl- 4 phenyl-1,3,2 dioxaphosphorinan 2 oxide, [ ] C P FW P C 3 (+)-Chloromethyl isomenthyl ether, [ ] C FW C (+)-Chloromethyl menthyl ether, [ ] C FW C C 3 C 3 C 3 ( )-Chloromethyl menthyl ether, [ ] C FW C (R)-(+)--(1 Phenylethyl)maleimide, [ ] C FW C 3 C 3 3C (S)-( )--(1 Phenylethyl)maleimide, [ ] C FW C (S)-( )-2 ydroxy-4-(2 methoxy- phenyl)-5,5 dimethyl- 1,3,2 dioxaphosphorinane 2 oxide, [ ] C P FW C C 3 P (R)-(+)-2 ydroxy-4-(2 methoxy- phenyl)-5,5 dimethyl- 1,3,2 dioxaphosphorinane 2 oxide, [ ] C P FW (S)-( )-1,2 Epithiododecane [ ] C S FW C P C 3 C 3 S C2(C2)8 (R)-(+)-Aminoglutethimide, [ ] C FW (S)-( )-Aminoglutethimide, [ ] C FW C 3 (+)-Allylboronic acid pinanediol ester, C 13 21B 2 FW C C 3 B (4S)-4-[(1R)-2 Azido-1-(benzyloxy) ethyl]-2,2 dimethyl-1,3 dioxolane C FW C (2R,5S)-5 Methyl-4,4 diphenyl- 1,3,2 dioxathiolane, [ ] C S FW C2 3C Ph Ph S (1R)-( )-opol benzyl ether, 95% [ ] C FW C 72 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

73 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 ml $47.50 References: (1) Sold under license from Zymes, LLC. (2) (a) Lipshutz, B.. et al. rg. Lett. 2008, 10, (b) Lipshutz, B.. et al. Adv. Synth. Catal. 2008, 350, 953. (c) Lipshutz, B.. et al. rg. Lett. 2008, 10, (d) Lipshutz, B..; Taft, B. R. rg. Lett. 2008, 10, (e) Lipshutz, B..; Ghorai, S. Aldrichimica Acta 2008, 41, in press. (f) Lipshutz, B.. et al. rg. Lett. 2008, 10, ASAP. sigma-aldrich.com

74 $ 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.

75 $ 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

76 Risk & Safety Cat. o. Risk Safety Xi: 36/37/ Xi: 36/37/ / Xn: 22-37/ / T: 23/24/ /37/ Xn: 20/21/22-36/37/ Xi: 37/ T: 45-20/21-37/ / /37/ C: /37/ Xn: 22-36/37/ Xn: 22-37/ Xn: Xn: 22-36/37/ F: Xi: 37/ C: /37/ C: /37/ Xi: 36/37/ C: 21/ /37/ C: 21/ /37/ Xn: 22-36/37/ Xn: 22-36/37/ Xi: 36/37/ Xi: 36/37/ C: /37/ Xi: 36/37/ / F,Xi: / T: 23/ /37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ / Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: Xi: 36/37/ Xn: Xi: 36/37/ Xi: 36/37/ C: /37/ C: /37/ Xi: 36/37/ /37/ C: /37/ C: /37/ C: /37/ F,C: /37/ Xi: 36/ Xi: 36/37/ Xi: 36/37/ Xi: / / Xi: 36/37/ Xn: 21/ / C: /37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ / F: / T: 25-37/ Xi: 36/37/ / Xn: 22-36/37/ / Xi: 36/37/ Cat. o. Risk Safety Xi: 36/37/ / / Xi: 36/37/ Xi: 36/37/ Xi,: / Xi: 36/37/ C: /37/ / / Xn: 36/37/38-42/ / Xn: 36/37/ Xn: 36/37/ Xi: 36/37/ Xi: 37/ C: /37/ / Xi: 10-36/ Xi: 36/37/ Xi: 37/ Xi: 10-36/ / Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 10-36/ / C: C: F,C: 11-20/21/ /37/ / Xn: Xi: 36/37/ Xi: 36/37/ / / / T,: / /37/ C: /37/ Xn: / Xi: 36/37/ Xn: 10-20/21/ Xn: /25-36/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ / / Xi: 10-36/37/ C: /37/ C: /37/ / / Xi: 36/ Xi: 36/37/ /37/ / / / / / / Xi: 36/37/ Xi: 36/37/ Xn: / Xn: / / / Xi: 10-36/37/ /25 76 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

77 Cat. o. Risk Safety Xi: / / / / / Xn: / Xi: 36/37/ Xi: 36/37/ Xi: 10-36/37/ Xi: 10-36/ T+: 26/27/ /37/ F,Xi: 11-36/37/ Xn: Xn: Xi: 36/37/ Xi: 36/37/ / Xi: 36/37/ Xi: 36/37/ C: /37/ Xn: T: 23/24/25-36/37/38-42/ /37/ Xi: 36/37/ / C: /37/ Xn: / / Xi: 36/37/ T: 25-36/37/ /37/ / C: 10-20/21/ /37/ Xi: 36/37/ T: 45-20/21-37/ / /37/ Xn: 36/37/38-42/ / F,C,: 11-20/ /37/ F,C,: 11-20/ /37/ / Xi: 36/37/ Xn: 10-20/21/ /37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ C: /37/ Xi: 36/37/ Xi: 36/37/ /37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ / Xi: 36/37/ Xi: 36/37/ C: /37/ C: /37/ Xn: 20/21/22-36/37/ Xn: 20/21/22-36/37/ / Xi: 36/37/ Xi: 36/37/ T: Xi,: 10-36/37/ / Xi: 36/37/ / Xi: 36/37/ /37/ Xi: 36/37/ / Xi: 36/37/ C: 21/ /37/ C: C: /37/39-45 Cat. o. Risk Safety Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: / Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xn: 22-36/37/ / Xi: 36/37/ / Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 10-36/37/ Xi: 36/37/ Xi: 36/37/ Xn: 22-36/37/ Xn: Xi: 36/37/ Xi: 36/37/ / Xi: 36/37/ Xn: Xi: 10-36/37/ Xn: / Xi: 36/37/ Xi: 36/37/ / Xi: 36/37/ / Xi: 36/37/ / Xi: 36/37/ / Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ /37/ F,Xi: Xi: C: 10-21/ /37/ C: /37/ Xi: 36/37/ Xi: 36/37/ Xn: 22-36/37/38-42/ / Xi: 36/37/ F,Xi: Xi: 36/37/ / Xi: 36/37/ / Xn: 20/21/22-36/37/ Xi: 36/37/ Xi: 36/37/ /37/ Xn: 22-36/37/ / Xi: 36/37/ / Xn: Xi: 36/37/ / / Xi: 36/37/ / Xi: 36/37/ / Xi: 36/37/ / Xi: / C: /37/ C: /37/ / / Xi: 36/37/ / C: /37/ /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

78 Risk & Safety Cat. o. Risk Safety / Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ / Xi: 36/37/ Xi: 36/37/ / Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ / Xi: 36/37/ Xi: 36/37/ Xi: Xi: 36/37/ / Xi: 36/37/ / / Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ / Xi: 36/37/ / Xi: 36/37/ / Xi: 36/37/ / Xi: 36/37/ Xi: 36/37/ / C: /37/ Xn: 20/21/22-36/37/ Xi: 36/37/ Xi: 36/37/ / / Xi: 36/37/ Xi: 36/37/ / C: /37/ C: /37/ / Xi,: / Xi,: 36/37/38-51/ Xn: / / / Xi: 36/37/ / Xi: 36/37/ / T: /37/ Xi: 36/37/ / / / / / Xi: 36/37/ / / C: /37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ / Xi: 36/37/ / Xi: 36/37/ T+: 26/27/ / Xi: 36/37/ / Xn: 20/21/ /37/ C: 20/21/ /37/ Xn: 22-36/37/ F: 11-36/37/ /37/ F,Xi: 11-36/37/ Xn: 22-37/ Cat. o. Risk Safety Xn: 20/21/ /37/ Xi: 36/37/ Xi: 36/37/ / C: 20/21/ Xn,: 10-20/21/22-36/37/ / Xi: 36/37/ C: 20/21/ /37/ C: 20/21/ /37/ Xn: 22-36/ T: / Xi: 36/37/ Xn: 21-37/ /37/ Xi: 36/37/ Xn: 20/21/22-36/37/ Xi: 36/37/ / Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 10-36/37/ /37/ Xi: 10-36/37/ /37/ Xn: 22-37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ F,C: /37/ Xi: 36/37/ Xi: 36/37/ Xn: 10-21/22-36/37/ / Xn: 20/21/22-36/37/ Xn: 20/21/ F,: 11-51/ / / Xi: 36/37/ / F: Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/ Xi: 36/37/ Xi: 36/37/ Xi: 10-36/37/ Xi: 36/37/ Xi: 36/37/ Xn: 20/21/22-36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ / Xn: 22-36/37/ / Xi: / / Xn: 22-36/37/ /37/ Xn: 22-36/37/ /37/ Xn: Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ / Xn: /39 78 sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

79 Cat. o. Risk Safety Xi: 36/37/ Xi: 36/37/ Xi,: 10-50/ / Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/ C: /37/ / Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ / Xn: 20/21/ / Xi: 36/37/ C: /37/ F,Xi: /37/ F,Xi: /37/ Xi: 36/37/ T: 23/24/ / T: 25-36/37/ Xi: Xi: Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xn: 20/21/ Xn: 20/21/ Xn: 20/21/ Xi: 36/37/ Xi: 36/37/ Xi: Xi: / C: /37/ C: /37/ / / Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ C: /37/ C: 20/21/ /37/ Xi: 36/37/ Xi: 10-36/37/ Xi: 10-36/37/ Xi: 36/37/ F,T+: 11-26/27/28-36/ /37/ Xi: 36/37/ Cat. o. Risk Safety Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ T+: 10-26/28-36/37/ /37/ Xi: 36/37/ : 51/ C: 20/21/ /37/ Xi: 36/37/ Xi: 36/37/ T: 23/24/25-36/37/ /37/ Xn: 20/21/22-36/37/ / Xn: 20/21/22-36/37/ / Xn: 20/21/ Xi: 36/37/ / / Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xn: 22-36/37/38-50/ C: /37/ Xi: Xi: 36/37/ Xi: 36/37/ Xi: 41-52/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ C: /37/ C: /37/ Xi: T: / /37/ /37/ Xi: 36/37/ Xi: 36/37/ F,Xn: /37/ Xi: 10-36/37/ /37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 37/ Xi: 36/37/ Xi: 36/37/ / C: /37/ C: /37/ Xi: 36/37/ Xi: 36/37/ T: / / /37/ T: /37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ / Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xn: 22-52/ Xi: 36/37/ C: /37/ Xn: 22-52/ Xi: 36/37/ F,Xn: /37/ Xi: 36/37/ Xi: 36/37/ Xi: 5-36/37/ C: /37/ Xi: 36/37/ Xn: 22-37/ 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

80 Risk & Safety Cat. o. Risk Safety Xn: 20/21/22-36/37/ / Xn: 22-36/37/ C: /37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: / Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ F,Xi: 11-36/37/ Xi: 36/37/ / C: /37/ Xn: 22-36/37/ Xi: 36/37/ Xn: 20/21/22-36/37/ Xn: 22-36/37/ Xi: 36/37/ Xi: 36/37/ F,T: 20/21/ /37/ F,T: 20/21/ /37/ C: Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xn: 20/21/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ C: /37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ F+,T: 45-20/21/ F+,T: T: T: T: /24/ T: /24/ T: T: 45-20/21-36/ / T,: / /37/ T,: / Xi: 36/37/ Xi: 36/37/ Xi,: Xi: 36/37/ Xi: 36/37/ T: /37/ Xi: 36/37/ Xi: 36/37/ Xn: Xi: 10-36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Cat. o. Risk Safety Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ / Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ / Xn: 20/21/22-36/37/ / / Xi: / Xi: / C: /37/ Xi: 36/37/ Xi: 10-36/37/ /37/ Xi: 36/37/ Xi: 36/37/ / Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xn: / Xi: 36/37/ Xi: 36/37/ Xn: Xi: 36/37/ Xi: 36/37/ Xn: 22-37/ / Xn: 36/37/38-42/ Xi: 36/37/ Xn: 22-37/ / Xn: 36-42/ T: 25-36/37/38-42/ /37/ T: / /37/ Xn: 22-37/ / Xn: 22-37/ / C: /37/ Xi: 37/ T: 25-37/ Xn: sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

81 Cat. o. Risk Safety Xn: 22-36/37/ Xn: 22-36/37/ Xn: Xn: Xn: /37/ Xn: 22-36/37/ /37/ Xi: 36/37/ Xi: 36/37/ Xn,: 22-37/ / /37/ Xn,: 22-37/ / /37/ Xi: 36/37/ F,C: /37/ Xi: 36/37/ Xi: 36/37/ Xn: 22-36/37/ Xn: 22-36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ T: 25-36/37/ T: 25-36/37/ Xn: /37/ Xi: 36/37/ Xi: 36/37/ Xn: / Xn: / / Xn: 22-36/37/ Xn,: 22-36/37/ Xn: 22-36/37/ Xn: 22-36/37/ C: /37/ C: /37/ T: Xi: 36/37/ Xi: 36/37/ Xn: 22-36/37/ / Xn: Xn: 22-36/37/ F,Xn: /37/ F+: Xi: 37/ /37/ Xn: 22-37/ Xi: 36/37/ F+: F,C: /37/ F,C: /37/ C,: 34-51/ /37/ Xi,: 36/37/38-51/ C: /37/ Xn: Xn: Xn: Xn: 22-36/37/ Xn: 22-36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ C: /37/ C: /37/ Xn,: Xn,: Xn: Xn: C: /37/ Xn,: Xn,: Xi: C: 21/ /37/ Xi: Cat. o. Risk Safety Xi: 36/37/ Xn: Xi: 36/37/ Xi: 36/37/ Xi: 37/ Xn: 22-37/ Xn: Xi: Xi: Xi: Xn: 22-36/37/ Xn: 22-36/37/ F,C: /37/ Xi: 36/37/ Xn: 22-36/37/ / Xn: 22-36/37/ F,Xn: 11-20/21/22-36/37/ F,Xn,: /37/ Xn: : Xn: Xn: 22-37/ Xi: 36/37/ Xn: T: Xn: Xn: Xn: 22-36/37/ Xn: 22-36/37/ Xn: 20/21/22-36/37/ Xn: / Xn: 20/21/22-36/37/ Xn: 20/21/22-36/37/ T: 25-37/ /37/ Xi: 36/37/ Xi: 36/37/ / Xi: 36/37/ / Xi: 36/37/ T,: 25-37/ T,: C: /37/ Xn: Xn: 22-37/ Xi: 36/37/ Xn: Xi: / Xi: 36/ Xi: Xi: 36/37/ Xi: / Xn: 20/21/ / Xi: 36/37/ Xi: 36/37/ Xi: / Xn: Xn: 10-21/22-36/37/ / Xi: 36/37/ C: /37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xi: 36/37/ Xn: Xi: 36/37/ F,Xn: /37/ Xi: 36/37/ Xi: 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

82 Risk & Safety Cat. o. Risk Safety Xn: Xi: 36/37/ C: /37/ F,C: 11-20/21/ /37/ C,: /37/ C: /37/39-45 A154 Xi: 36/37/ A6801 Xi: 36/37/ A70704 Xn: 22-36/37/ A70909 Xn: 42/ /37 A76206 C: /37/39-45 A83407 Xn: /25 B60002 Xi: 36/37/ /39 C003 T: 23/24/ /37/39-45 C2107 C: /37/39-45 C301 F: Cat. o. Risk Safety C409 Xn: E34102 Xi: G2410 Xi: 36/37/ I13901 F,Xi: M1125 Xi: 37/ M /25 M2780 Xi: 37/ M3000 Xi: 36/37/ M /37/39 M3933 F,T: 11-23/24/25-39/23/24/ /37-45 M Xi: 36/37/ /25 T109 Xi: 36/37/ V104 Xn: 20/21/ sigma-aldrich.com T RDER: Contact your local Sigma-Aldrich office (see back cover) or visit sigma-aldrich.com/chemicalsynthesis.

83 ew Aldrich andbook! ver 6,000 Innovative ew Products Request your copy of the new Aldrich andbook set today 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