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726583

Sigma-Aldrich

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

grade

produced by BASF

vapor pressure

0.5 mmHg ( 20 °C)

assay

≥99.0% (GC)
≥99.0%

form

liquid

optical purity

enantiomeric excess: ≥99.0%

refractive index

n20/D 1.526 (lit.)

bp

187 °C (lit.)

density

0.94 g/mL at 25 °C (lit.)

functional group

amine
phenyl

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

  • 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_germany

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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Shao-Hua Huang et al.
Magnetic resonance in chemistry : MRC, 47(5), 423-427 (2009-02-19)
Two types of chiral analytes, the urea and amide derivatives of alpha-phenylethylamine, were prepared. The effect of inter-molecular hydrogen-bonding interaction on self-discrimination of the enantiomers of analytes has been investigated using high-resolution (1)H NMR. It was found that the urea
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
Manuel Algarra et al.
Journal of separation science, 33(2), 143-154 (2009-12-31)
Free fatty acids were derivatized as amides (DFFA) by reaction with (R)-(+)-1-phenylethylamine, using a simple, fast and robust reaction scheme. A HPLC method with diode array and ESI MS detection was developed for the analysis of the derivatized substances. Six
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.
G Palaprat et al.
The journal of physical chemistry. B, 111(31), 9239-9243 (2007-07-20)
A polydomain cholesteric elastomer was obtained by cross-linking a nematic side-chain polysiloxane in the presence of a chiral dopant. After extraction of the chiral dopant, sorption experiments were performed, by the use of an electronic microbalance, in the presence of
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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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