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Merck
CN

726583

(S)-(−)-α-Methylbenzylamine

ChiPros®, produced by BASF, ≥99.0%

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
UNSPSC Code:
12352116
NACRES:
NA.22
PubChem Substance ID:
329764248
EC Number:
220-098-0
Beilstein/REAXYS Number:
2204907
MDL number:
MFCD00064406

Key Documents

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Product Name

(S)-(−)-α-Methylbenzylamine, ChiPros®, produced by BASF, ≥99.0%

InChI key

RQEUFEKYXDPUSK-ZETCQYMHSA-N

InChI

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

SMILES string

C[C@H](N)c1ccccc1

vapor pressure

0.5 mmHg ( 20 °C)

description

Drug Control: Pszichotróp anyag / Psychotropic Substance (Hungary), 78/2022. (XII. 28.) BM rendelet.

assay

≥99.0% (GC)
≥99.0%

form

liquid

optical purity

enantiomeric excess: ≥99.0%

drug control

Pszichotróp anyag / Psychotropic Substance (Hungary), 78/2022. (XII. 28.) BM rendelet

refractive index

n20/D 1.526 (lit.)

bp

187 °C (lit.)

density

0.94 g/mL at 25 °C (lit.)

functional group

amine
phenyl

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Application

  • The first example of a diastereoselective thio-Ugi reaction: a new synthetic approach to chiral imidazole derivatives.: This research presents a novel diastereoselective thio-Ugi reaction, enabling the synthesis of chiral imidazole derivatives, which are essential in asymmetric synthesis and pharmaceutical intermediates (Gulevich et al., 2007).
  • Synthesis and serotonin receptor affinities of a series of enantiomers of alpha-methyltryptamines: evidence for the binding conformation of tryptamines at serotonin 5-HT1B receptors.: This study investigates the synthesis and serotonin receptor affinities of alpha-methyltryptamine enantiomers, contributing to the understanding of chiral compounds in medicinal chemistry (Nichols et al., 1988).

Legal Information

ChiPros is a registered trademark of BASF SE

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

WGK 1

flash_point_f

158.0 °F - closed cup

flash_point_c

70 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
BCBS1085V
BCBT9799
BCBL3421V
BCBC4054V
BCBC4054

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Antoine Fadel et al.
The Journal of organic chemistry, 72(5), 1780-1784 (2007-01-30)
Enantiomerically pure (R)-(+)-pipecolic acid was synthesized in four steps and 42% overall yield starting from dihydropyran and (R)-alpha-methylbenzylamine. A general short strategy is also described for preparing (S)-proline (47.5% overall yield) and derivatives.
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
Carlos Fernandes et al.
The Journal of organic chemistry, 74(8), 3217-3220 (2009-03-17)
A short, convenient, gram scale protocol has been established to allow facile access to all four stereoisomers of 2-aminocyclobutanecarboxylic acid, each in enantiomerically pure form (ee >99%). Starting from the readily available cis racemate, the procedure combines efficient alpha-phenylethylamine derivative
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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ChiPros Chiral Amines

Chiral amines play an important role in stereoselective organic synthesis. They are used directly as resolving agents, building blocks, or chiral auxiliaries.

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