(S)-α-Methylbenzylamine

Abstract

[2627-86-3] C8H11N (MW 121.20) InChI = 1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3/t7-/m0/s1 InChIKey = RQEUFEKYXDPUSK-ZETCQYMHSA-N (resolving agent for carboxylic acids;7-11 determination of enantio purity of carboxylic acids;16, 17 stereospecific reactions of carbonyl compounds;18 reductive amination of carbonyl compounds29, 30) Alternate Name: (S)-phenylethylamine;(S)-PEA. Physical Data: bp 187 °C; d 0.940 g cm−3; [α]D −39° (neat). Solubility: readily sol all organic solvents. Form Supplied in: both enantiomers are commercially available. Analysis of Reagent Purity: the enantiomeric purity of the reagent can be assessed by NMR analysis of the corresponding Mosher's amide.4 Chiral complexing reagents (such as 1,1′-binaphthyl-2,2′-diylphosphoric acid) have also been used in the direct NMR analysis of the reagent.5, 6 Preparative Methods: racemic α-methylbenzylamine has been resolved utilizing chiral acids such as tartaric acid1 and (S)-(−)-carbamalactic acid,2 among others. Chiral resolution can also be effected by enzymatic resolution.36 Several stereospecific syntheses have been reported.3 Handling, Storage, and Precaution: stable at rt for extended periods of time when stored under nitrogen.