(R)-benzyl 1-cyanoethylcarbamate

Base Information

• Chemical Name: (R)-benzyl 1-cyanoethylcarbamate
• CAS No.: 176894-58-9
• Molecular Formula: C11H12N2O2
• Molecular Weight: 204.228
• DSSTox Substance ID: DTXSID10443722
• Nikkaji Number: J1.783.519J
• Wikidata: Q72458125
• Mol file: 176894-58-9.mol

Synonyms:(R)-benzyl 1-cyanoethylcarbamate;176894-58-9;Benzyl N-[(1R)-1-cyanoethyl]carbamate;(R)-Benzyl (1-cyanoethyl)carbamate;SCHEMBL6312473;DTXSID10443722;RKPTZVZVBGXQSI-SECBINFHSA-N;(R)-Benzyl(1-cyanoethyl)carbamate;benzyl[(1r)-1-cyanoethyl]carbamate;MFCD18633364;benzyl [(1R)-1-cyanoethyl]carbamate;(R)-2-(Benzyloxycarbonylamino)propiononitrile;A26819;I11774;EN300-9437300

Chemical Property of (R)-benzyl 1-cyanoethylcarbamate

Chemical Property:

• Melting Point: 82-83℃
• PSA: 65.61000
• Density: 1.148
• LogP: 2.02928
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 204.089877630
• Heavy Atom Count: 15
• Complexity: 251

Purity/Quality:

97% ^*data from raw suppliers

(R)-Benzyl(1-cyanoethyl)carbamate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C#N)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: C[C@H](C#N)NC(=O)OCC1=CC=CC=C1

Technology Process of (R)-benzyl 1-cyanoethylcarbamate

There total 4 articles about (R)-benzyl 1-cyanoethylcarbamate 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: 97.0%

benzyl [(1R)-2-amino-1-methyl-2-oxoethyl]carbamate (151378-81-3) → (2R)-2-(benzyloxycarbonylamino)propionitrile (176894-58-9)

Guidance literature:

With pyridine; p-toluenesulfonyl chloride; In dichloromethane; at 0 - 20 ℃;

DOI:10.3390/molecules25061315

Reference yield:

N-benzyloxycarbonyl-D-alanine (26607-51-2) → (2R)-2-(benzyloxycarbonylamino)propionitrile (176894-58-9)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / tetrahydrofuran / 0.17 h / -15 °C

2: gaseous NH₃ / tetrahydrofuran / 1.5 h / -15 - 20 °C

3: 86 percent / p-TsCl; pyridine / CH₂Cl₂ / 3.5 h / 0 - 20 °C

With pyridine; ammonia; triethylamine; p-toluenesulfonyl chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm991119p

Reference yield:

C16H21NO6 (102988-93-2) → (2R)-2-(benzyloxycarbonylamino)propionitrile (176894-58-9)

Guidance literature:

Multi-step reaction with 2 steps

1: gaseous NH₃ / tetrahydrofuran / 1.5 h / -15 - 20 °C

2: 86 percent / p-TsCl; pyridine / CH₂Cl₂ / 3.5 h / 0 - 20 °C

With pyridine; ammonia; p-toluenesulfonyl chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm991119p

upstream raw materials:

benzyl [(1R)-2-amino-1-methyl-2-oxoethyl]carbamate

N-benzyloxycarbonyl-D-alanine

C₁₆H₂₁NO₆

N-benzyloxycarbonyl-D-alanine methyl ester

Downstream raw materials:

benzyl N-[(1R)-1-(1H-1,2,3,4-tetrazol-5-yl)ethyl]carbamate

benzyl [(1R,2Z)-2-amino-2-(hydroxyimino)-1-methylethyl]carbamate

benzyl [(1R)-1-(5-methyl-1,2,4-oxadiazol-3-yl)ethyl]carbamate