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115568

Sigma-Aldrich

(S)-(−)-α-Methylbenzylamine

98%

Synonym(s):

(S)-(-)-alpha-Methylbenzylamine, (S)-(−)-1-Phenylethylamine

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About This Item

Linear Formula:
C6H5CH(CH3)NH2
CAS Number:
2627-86-3
Molecular Weight:
121.18
Beilstein/REAXYS Number:
2204907
EC Number:
220-098-0
MDL number:
MFCD00064406
UNSPSC Code:
12352116
PubChem Substance ID:
24847225
NACRES:
NA.22

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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Application

(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.
Used in a one-pot, multi-component synthesis of a highly substituted, chiral pyrrole.

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

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

Storage Class

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

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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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)
Karim Engelmark Cassimjee et al.
Organic & biomolecular chemistry, 10(28), 5466-5470 (2012-06-13)
For biocatalytic production of pharmaceutically important chiral amines the ω-transaminase enzymes have proven useful. Engineering of these enzymes has to some extent been accomplished by rational design, but mostly by directed evolution. By use of a homology model a key
Bartosz Lewandowski et al.
Chemical communications (Cambridge, England), (47)(47), 6399-6401 (2008-12-03)
Simple chiral aza-crown ethers based on sucrose display high enantioselectivity in complexation of phenylethylammonium chlorides.
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