Methyl N-cyanobenzimidate

Base Information

• Chemical Name: Methyl N-cyanobenzimidate
• CAS No.: 6041-23-2
• Molecular Formula: C9H8 N2 O
• Molecular Weight: 160.175
• European Community (EC) Number: 227-927-5
• DSSTox Substance ID: DTXSID001297036
• Nikkaji Number: J227.247D
• Mol file: 6041-23-2.mol

Synonyms:Methyl N-cyanobenzimidate;6041-23-2;methyl N-cyanobenzenecarboximidate;EINECS 227-927-5;AI3-61761;N-Cyano benzenecarboximidic acid methyl ester;N-Cyanobenzimidic Methyl Ester;Benzenecarboximidic acid, N-cyano-, methyl ester;MethylN-cyanobenzimidate;(Z)-methyl N-cyanobenzimidate;SCHEMBL3455076;SCHEMBL3455077;DTXSID001297036;N-Cyanobenzimidic acid methyl ester;AKOS006277553;SB75905

Chemical Property of Methyl N-cyanobenzimidate

Chemical Property:

• Vapor Pressure: 0.0459mmHg at 25°C
• Boiling Point: 237°C at 760 mmHg
• PKA: -4.14±0.50(Predicted)
• Flash Point: 97.1°C
• PSA: 45.38000
• Density: 1.02g/cm³
• LogP: 1.56068
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 160.063662883
• Heavy Atom Count: 12
• Complexity: 208

Purity/Quality:

98%Min ^*data from raw suppliers

N-CYANOBENZIMIDIC METHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=NC#N)C1=CC=CC=C1

Technology Process of Methyl N-cyanobenzimidate

There total 6 articles about Methyl N-cyanobenzimidate 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: 87.0%

methanol (67-56-1) + CYANAMID (420-04-2) + benzaldehyde (100-52-7) → methyl N-cyanobenzenecarboximidoate (6041-23-2)

Guidance literature:

methanol; CYANAMID; benzaldehyde; With sodium t-butanolate; at 20 ℃; for 0.5h;

With N-Bromosuccinimide; at 50 ℃; for 12h;

DOI:10.1021/ol902207h

Reference yield: 79.2%

CYANAMID (420-04-2) + orthobenzoic acid trimethyl ester (707-07-3) → methyl N-cyanobenzenecarboximidoate (6041-23-2)

Guidance literature:

With acetic anhydride; at 135 ℃; for 0.75h;

Reference yield: 59.0%

CYANAMID (420-04-2) + methyl benzimidate hydrochloride (5873-90-5) → methyl N-cyanobenzenecarboximidoate (6041-23-2)

Guidance literature:

With disodium hydrogenphosphate; sodium dihydrogenphosphate; In water; for 16h; Ambient temperature;

DOI:10.1055/s-1983-30355

upstream raw materials:

CYANAMID

orthobenzoic acid trimethyl ester

methanol

benzaldehyde

Downstream raw materials:

2-Amino-4-phenyl-6-thioxo-1,6-dihydro-pyrimidine-5-carbonitrile

2-amino-6-phenyl-5-phenylsulphonylpyrimidin-4(1H)-one

5-phenyl-1,2,4-oxadiazol-3-amine

3-phenyl-1,2,4-oxadiazol-5-amine

Refernces

• 1、 Yin, Ping,Wen-Bo, Ma.,Chen, Yue,Huang, Wen-Cal,Deng, Yong,He, Ling. "Highly efficient cyanoimidation of aldehydes". supporting information; experimental part. p. 5482 - 5485. Retrieved 2010/02/27.
• 2、 Perez, Miguel A.,Soto, Jose L.,Carrillo, Jose R.. "A Simple, Unambiguous Synthesis of 2-Amino-4-oxo- and -4-thioxo-3,4-dihydropyrimidine-5-carbonitriles". . p. 402 - 404. Retrieved 2007/10/02.