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115568

Sigma-Aldrich

(S)-(−)-α-Methylbenzylamine

98%

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Synonym(s):
(S)-(-)-alpha-Methylbenzylamine, (S)-(−)-1-Phenylethylamine
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

vapor pressure

0.5 mmHg ( 20 °C)

Quality Level

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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This Item
237450427470220566
(S)-(−)-α-Methylbenzylamine 98%

115568

(S)-(−)-α-Methylbenzylamine

(S)-(−)-1-(1-Naphthyl)ethylamine ≥99%

237450

(S)-(−)-1-(1-Naphthyl)ethylamine

Quality Level

100

Quality Level

100

Quality Level

-

Quality Level

100

density

0.94 g/mL at 25 °C (lit.)

density

1.067 g/mL at 20 °C (lit.)

density

1.01 g/mL at 25 °C (lit.)

density

1.045 g/mL at 20 °C (lit.)

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

2-8°C

bp

187 °C (lit.)

bp

153 °C/11 mmHg (lit.)

bp

171 °C/15 mmHg (lit.)

bp

55-56 °C/2.5 mmHg (lit.)

refractive index

n20/D 1.526 (lit.)

refractive index

n20/D 1.623 (lit.)

refractive index

n20/D 1.563 (lit.)

refractive index

n20/D 1.5145 (lit.)

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

CorrosionSkull and crossbones

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


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Customers Also Viewed

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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)
Sachin R Chaudhari et al.
Organic & biomolecular chemistry, 10(31), 6410-6419 (2012-06-28)
The three-component chiral derivatization protocols have been developed for (1)H, (13)C and (19)F NMR spectroscopic discrimination of chiral diacids by their coordination and self-assembly with optically active (R)-α-methylbenzylamine and 2-formylphenylboronic acid or 3-fluoro-2-formylmethylboronic acid. These protocols yield a mixture of
Hyungdon Yun et al.
Bioscience, biotechnology, and biochemistry, 72(11), 3030-3033 (2008-11-11)
To produce (S)-alpha-methylbenzylamine (MBA) from acetophenone, recombinant Escherichia coli co-expressing omega-transaminase and acetolactate synthase was used as a whole-cell biocatalyst. The solvent-bridge reaction system increased the yield of the whole-cell reaction by 2.5-fold, and the inhibitory (S)-alpha-MBA produced in the

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