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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:
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

Signal Word

Danger

Hazard Statements

H302,H311,H314

Hazard Classifications

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
R Moaddel et al.
Chirality, 17(8), 501-506 (2005-08-23)
A liquid chromatography stationary phase containing immobilized membranes obtained from a cell line that expresses the human organic cation transporter (hOCT1-IAM) has been used to study the binding of the enantiomers of propranolol, atenolol, pseudoephedrine, and alpha-methylbenzylamine to the immobilized
Abraham R Martin et al.
Applied microbiology and biotechnology, 76(4), 843-851 (2007-06-22)
Enzyme immobilization often improves process economics, but changes in kinetic properties may also occur. The immobilization of a recombinant thermostable (S)-aminotransferase was made by entrapment on calcium alginate-3% (w/v)-and tested with (S)-(-)-(alpha)-methylbenzylamine for acetophenone production. The best immobilization results were
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