(2S)-2-amino-3-phenylpropanenitrile

Base Information

• Chemical Name: (2S)-2-amino-3-phenylpropanenitrile
• CAS No.: 73148-70-6
• Molecular Formula: C₉H₁₀N₂
• Molecular Weight: 146.192
• UNII: T365NQ3WVE
• Nikkaji Number: J643.245J
• Mol file: 73148-70-6.mol

Synonyms:(2S)-2-amino-3-phenylpropanenitrile;73148-70-6;Phenylalanine nitrile;(S)-2-Amino-3-phenylpropanenitrile;T365NQ3WVE;2-Amino-3-phenylpropanenitrile, (S)-;UNII-T365NQ3WVE;Benzenepropanenitrile, alpha-amino-, (alphaS)-;SCHEMBL2921309;AVXNAHRDJXOJHT-VIFPVBQESA-N;(alphaS)-alpha-Aminobenzenepropanenitrile;Benzenepropanenitrile, alpha-amino-, (S)-;CS-0112121;(.ALPHA.S)-.ALPHA.-AMINOBENZENEPROPANENITRILE;BENZENEPROPANENITRILE, .ALPHA.-AMINO-, (S)-;BENZENEPROPANENITRILE, .ALPHA.-AMINO-, (.ALPHA.S)-

Chemical Property of (2S)-2-amino-3-phenylpropanenitrile

Chemical Property:

• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 146.084398327
• Heavy Atom Count: 11
• Complexity: 150

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C#N)N
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C#N)N

Technology Process of (2S)-2-amino-3-phenylpropanenitrile

There total 13 articles about (2S)-2-amino-3-phenylpropanenitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(S)-N-benzyloxycarbonyl-2-amino-3-phenyl-propionitrile (21947-21-7) → α(L)-aminobenzylacetonitrile (73148-70-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In 1,4-dioxane; for 16h;

DOI:10.1039/c6cc07530d

Reference yield: 91.0%

(S)-2-(tert-butoxycarbonylamino)-3-phenylpropanenitrile (99281-90-0) → α(L)-aminobenzylacetonitrile (73148-70-6)

Guidance literature:

With formic acid; at 20 ℃; for 16h;

DOI:10.1016/j.bmc.2019.115083

Reference yield:

(S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide (88463-18-7,35150-06-2) → α(L)-aminobenzylacetonitrile (73148-70-6)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic anhydride; pyridine / 0.5 h / 20 °C

2: methane sulfonic acid / tetrahydrofuran / 18 h / 20 °C

With pyridine; methanesulfonic acid; trifluoroacetic anhydride; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2007.05.024

upstream raw materials:

(S)-2-(2-Nitro-phenylsulfanylamino)-3-phenyl-propionamide

(S)-2-(tert-butoxycarbonylamino)-3-phenylpropanenitrile

(-)-1-<(1-cyano-2-phenylethyl)amino>-2R-methyl-5R-(1-methylethenyl)cyclohexane-1R,3R-dicarbonitrile

(S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide

Downstream raw materials:

(S)-2-[(S)-1-(4-bromo-phenyl)-2,2,2-trifluoro-ethylamino]-N-[(S)-1-cyano-2-phenyl-ethyl]-3-methyl-butyramide

L-Phenylalanine amide

(S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide

N-tert-butoxycarbonyl-L-phenylalanine