Methyl 4-chloro-2-cyanobenzoate

Base Information

• Chemical Name: Methyl 4-chloro-2-cyanobenzoate
• CAS No.: 58331-97-8
• Molecular Formula: C₉H₆ClNO₂
• Molecular Weight: 195.605
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID40434486
• Wikidata: Q72489181
• Mol file: 58331-97-8.mol

Synonyms:Methyl 4-chloro-2-cyanobenzoate;58331-97-8;METHYL4-CHLORO-2-CYANOBENZOATE;SCHEMBL12078300;DTXSID40434486;JKAWTBOCEPQPBQ-UHFFFAOYSA-N;MFCD08234732;AKOS006285251;AM84162;MB05672;DS-14169;CS-0042903;FT-0651059;A869473

Chemical Property of Methyl 4-chloro-2-cyanobenzoate

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 115-117 °C
• Refractive Index: 1.555
• Boiling Point: 305.824 °C at 760 mmHg
• Flash Point: 138.758 °C
• PSA: 50.09000
• Density: 1.327 g/cm³
• LogP: 1.99828
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 195.0087061
• Heavy Atom Count: 13
• Complexity: 245

Purity/Quality:

99% ^*data from raw suppliers

Methyl 4-chloro-2-cyanobenzoate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C=C(C=C1)Cl)C#N

Technology Process of Methyl 4-chloro-2-cyanobenzoate

There total 2 articles about Methyl 4-chloro-2-cyanobenzoate 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:

2-amino-4-chloro-benzoic acid methyl ester (5900-58-3) + copper(I) cyanide (544-92-3) → 4-chloro-2-cyanobenzoic acid methyl ester (58331-97-8)

Guidance literature:

With hydrogenchloride; sodium nitrite; Yield given. Multistep reaction; 2.) 70 deg C, 1 h;

DOI:10.1021/jm00102a016

Reference yield:

→ 4-chloro-2-cyanobenzoic acid methyl ester (58331-97-8)

Guidance literature:

entspr. Anthranilester, Cyanid;

Reference yield:

4-chloro-2-cyanobenzoic acid methyl ester (58331-97-8) → C20H13BrClFN2O5

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / ammonia gas / methanol / 72 h / Ambient temperature

2: 93 percent / 0.17 h / 160 °C

3: potassium carbonate / dimethylformamide / 1 h / 100 °C

4: dimethylsulfoxide / 2 h / Ambient temperature

5: 1.) hydrogen chloride / 1.) RT, 3 d, 2.) reflux, 4 h

With hydrogenchloride; ammonia; potassium carbonate; In methanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm00102a016

upstream raw materials:

2-amino-4-chloro-benzoic acid methyl ester

copper(I) cyanide

Downstream raw materials:

[2-(4-Bromo-2-fluoro-benzyl)-6-chloro-3-oxo-2,3-dihydro-isoindol-(1Z)-ylidene]-cyano-acetic acid ethyl ester

[2-(4-Bromo-2-fluoro-benzyl)-6-chloro-1-cyano-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-cyano-acetic acid ethyl ester

Refernces