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Sigma-Aldrich

3-(Benzylamino)propionitrile

97%

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About This Item

Linear Formula:
C6H5CH2NHCH2CH2CN
CAS Number:
706-03-6
Molecular Weight:
160.22
EC Number:
211-890-7
MDL number:
MFCD00001955
UNSPSC Code:
12352100
PubChem Substance ID:
24850672

Assay

97%

refractive index

n20/D 1.5308 (lit.)

density

1.024 g/mL at 25 °C (lit.)

functional group

amine
nitrile
phenyl

SMILES string

N#CCCNCc1ccccc1

InChI

1S/C10H12N2/c11-7-4-8-12-9-10-5-2-1-3-6-10/h1-3,5-6,12H,4,8-9H2

InChI key

MWTGBAURSCEGSL-UHFFFAOYSA-N

General description

3-(Benzylamino)propionitrile undergoes aza-type Michael reaction with 1-hydroxymethyl-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester under mild conditions.

Application

3-(Benzylamino)propionitrile was used as starting reagent in the synthesis of:
  • (3R,4S)-1-benzyl-4-phenylpyrrolidine-3-carboxylic acid, key chiral building block for synthesis of biologically active compounds
  • 1-{[benzyl-(2-cyano-ethyl)-amino]-methyl}-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester
  • 3-[benzyl-(3,5-dimethyl-pyrazol-1-ylmethyl)-amino]-propionitrile

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
12817AJ
07009DH
06909DH
04409JZ
05728LF

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A Practical and Efficient Synthesis of (3 R, 4 S)-1-Benzyl-4-phenylpyrrolidine-3-carboxylic acid via an Aziridinium Ion Intermediate.
Ohigashi A, et al.
Organic Process Research & Development, 14(1), 127-132 (2009)
1-{[Benzyl-(2-cyano-ethyl)-amino]-methyl}-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester.
Herrag L, et al.
Molbank, 1006(5), M494-M494 (2006)
3-[Benzyl-(1, 5-dimethyl-1H-pyrazol-3-ylmethyl)-amino]-propionitrile.
Herrag L, et al.
Molbank, 2006(5), M496-M496 (2006)

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