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M31104

Sigma-Aldrich

α-Methylbenzylamine

99%

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Synonym(s):
(±)-α-Methylbenzylamine, alpha-Methylbenzylamine, (±)-1-Phenylethylamine
Linear Formula:
C6H5CH(CH3)NH2
CAS Number:
618-36-0
Molecular Weight:
121.18
Beilstein:
636127
EC Number:
210-545-8
MDL number:
MFCD00008069
PubChem Substance ID:
24896793
NACRES:
NA.22

Assay

99%

form

liquid

refractive index

n20/D 1.526 (lit.)

bp

185 °C/756 mmHg (lit.)

density

0.94 g/mL at 25 °C (lit.)

SMILES string

CC(N)c1ccccc1

InChI

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

InChI key

RQEUFEKYXDPUSK-UHFFFAOYSA-N

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General description

α-Methylbenzylamine is a nitrogen source that is widely used as a representative substrate to study the chemo-enzymatic kinetic resolution of primary amines.

Application

α-Methylbenzylamine can be used as a reactant for the synthesis of dihydro-5H-dibenz[c,e]azepinium salts by reacting with racemic biphenol derivatives.
It is used in the synthesis of o-fluorobenzylamines.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302 + H312 - H314

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible, corrosive 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

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Palladium-Catalyzed ortho-Selective C-H Fluorination of Oxalyl Amide-Protected Benzylamines.
Chen, Changpeng et al.
The Journal of Organic Chemistry, 80(2), 942-949 (2014)
Jan Dines Knudsen et al.
Microbial cell factories, 15, 37-37 (2016-02-18)
Saccharomyces cerevisiae can be engineered to perform a multitude of different chemical reactions that are not programmed in its original genetic code. It has a large potential to function as whole-cell biocatalyst for one-pot multistep synthesis of various organic molecules
Kinetic resolution of ??methylbenzylamine with o?transaminase screened from soil microorganisms: Application of a biphasic system to overcome product inhibition.
Shin, Jong-Shik and Kim, Byung-Gee
Biotechnology and Bioengineering, 55(2), 348-358 (1997)
Chemoenzymatic dynamic kinetic resolution of primary amines.
Paetzold, Jens and Backvall, Jan E
Journal of the American Chemical Society, 127(50), 17620-17621 (2005)
Nora Weber et al.
Microbial cell factories, 16(1), 3-3 (2017-01-05)
Whole-cell biocatalysis based on metabolically active baker's yeast with engineered transamination activity can be used to generate molecules carrying a chiral amine moiety. A prerequisite is though to express efficient ω-transaminases and to reach sufficient intracellular precursor levels. Herein, the
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