115568

Sigma-Aldrich

(S)-(−)-α-Methylbenzylamine

98%

Synonym(s):
(S)-(−)-1-Phenylethylamine, (S)-(-)-alpha-Methylbenzylamine
Linear Formula:
C6H5CH(CH3)NH2
CAS Number:
Molecular Weight:
121.18
Beilstein/REAXYS Number:
2204907
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

vapor pressure

0.5 mmHg ( 20 °C)

assay

98%

optical activity

[α]20/D −39°, neat

optical purity

ee: 98% (GLC)

refractive index

n20/D 1.526 (lit.)

bp

187 °C (lit.)

density

0.94 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C[C@H](N)c1ccccc1

InChI

1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3/t7-/m0/s1

InChI key

RQEUFEKYXDPUSK-ZETCQYMHSA-N

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Related Categories

Application

Used in a one-pot, multi-component synthesis of a highly substituted, chiral pyrrole.
(S)-(-)-α-Methylbenzylamine along with 2-formylphenylboronic acid has been used in a derivatization protocol to analyze the enantiomeric excess of chiral diols.
It can also be used:
  • In the diastereoselective synthesis of S-aminonitriles.
  • As a chiral auxiliary in the synthesis of (S)-(-)-N-acetylcalycotomine or (R)-(+)-N-acetylcalycotomine.
  • As a chiral building block in the asymmetric synthesis of 1-substituted tetrahydro-β-carbolines.

Packaging

25, 100 g in glass bottle

pictograms

CorrosionSkull and crossbones

signalword

Danger

hazcat

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Skin Corr. 1B

storage_class_code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK Germany

WGK 1

Flash Point F

158.0 °F - closed cup

Flash Point C

70 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Ashwin R Bharadwaj et al.
Organic letters, 6(14), 2465-2468 (2004-07-02)
[reaction: see text] A multicomponent synthesis of highly substituted pyrroles catalyzed by thiazolium salts has been disclosed. The reaction employs an acyl anion conjugate addition reaction of acylsilanes (sila-Stetter) and unsaturated ketones to generate 1,4-dicarbonyl compounds in situ. The subsequent...
(S)-(-)-a-Methylbenzylamine as an efficient chiral auxiliary in enantiodivergent synthesis of both enantiomers of N-acetylcalycotomine.
Ziolkowski M, et al
Tetrahedron Asymmetry, 10(17), 3371-3380 (1999)
Lithium perchlorate/diethylether catalyzed aminocyanation of aldehydes
Heydari A, et al
Tetrahedron Letters, 39(19), 3049-3050 (1998)
Barry Lygo et al.
Organic & biomolecular chemistry, 10(25), 4968-4976 (2012-05-23)
A short synthetic route to diastereoisomeric atropos dihydro-5H-dibenz[c,e]azepinium salts via reaction of a single enantiomer of (R)-α-methylbenzylamine with a racemic atropos biphenol derivative is described. Compounds prepared via this approach are used to provide strong evidence that structurally related tropos...
Alejandra León et al.
Journal of natural products, 75(5), 859-864 (2012-05-12)
The enantiomeric lactams (-)-8, (+)-8, (+)-9, and (-)-9 were formed by the reaction of the dimeric phthalide rac-tokinolide B (rac-3) with (R)-(+)-α-methylbenzylamine and (S)-(-)-α-methylbenzylamine. The absolute configurations of compounds 8 and 9 were assigned by experimental and theoretically calculated electronic...

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