2-Cyanobenzoyl chloride

Base Information

• Chemical Name: 2-Cyanobenzoyl chloride
• CAS No.: 27611-63-8
• Molecular Formula: C8H4 Cl N O
• Molecular Weight: 165.579
• Hs Code.: 2926909090
• European Community (EC) Number: 248-572-2
• DSSTox Substance ID: DTXSID10182003
• Nikkaji Number: J250.558D
• Wikidata: Q83052659
• Mol file: 27611-63-8.mol

Synonyms:2-Cyanobenzoyl chloride;27611-63-8;2-cyanobenzoylchloride;Benzoyl chloride, 2-cyano-;2-cyano-benzoyl chloride;EINECS 248-572-2;2-Cyanbenzoylchlorid;o-cyanobenzoyl chloride;SCHEMBL1340299;DTXSID10182003;CBA61163;2-cyanobenzoyl chloride, AldrichCPR;MFCD00053279;AKOS006272646;FT-0652885;D87858

Chemical Property of 2-Cyanobenzoyl chloride

Chemical Property:

• Vapor Pressure: 0.00118mmHg at 25°C
• Refractive Index: 1.567
• Boiling Point: 299.6°Cat760mmHg
• Flash Point: 135°C
• PSA: 40.86000
• Density: 1.32g/cm³
• LogP: 1.93728
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 164.9981414
• Heavy Atom Count: 11
• Complexity: 205

Purity/Quality:

99% ^*data from raw suppliers

2-cyanobenzoyl chloride AldrichCPR ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Cyanobenzoyl chloride

There total 6 articles about 2-Cyanobenzoyl chloride 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-cyanobenzoic acid (3839-22-3) → 2-Cyanobenzoyl chloride (27611-63-8)

Guidance literature:

With phosphorus pentachloride; at 60 ℃;

Reference yield:

phthalamic acid (88-97-1) → 2-Cyanobenzoyl chloride (27611-63-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / Et₃N / CH₂Cl₂ / 8 h / 20 °C

2: 74 percent / aq. NaOH / methanol / 8 h / 20 °C

3: (COCl)2; DMF / CH₂Cl₂ / 2 h / 20 °C

With sodium hydroxide; oxalyl dichloride; triethylamine; N,N-dimethyl-formamide; In methanol; dichloromethane;

DOI:10.1248/cpb.53.764

Reference yield:

methyl 2-cyanobenzoate (6587-24-2) → 2-Cyanobenzoyl chloride (27611-63-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / aq. NaOH / methanol / 8 h / 20 °C

2: (COCl)2; DMF / CH₂Cl₂ / 2 h / 20 °C

With sodium hydroxide; oxalyl dichloride; N,N-dimethyl-formamide; In methanol; dichloromethane;

DOI:10.1248/cpb.53.764

upstream raw materials:

phthalimide

2-cyanobenzoic acid

phosphorus pentachloride

phthalamic acid

Downstream raw materials:

methyl 2-cyanobenzoate

Refernces

• 1、 Ansel, Annabel Q.,Montgomery, John. "Combined Cyanoborylation, C-H Activation Strategy for Styrene Functionalization". supporting information. p. 8538 - 8543. Retrieved 2020/11/12.
• 2、 Cederbalk, Anna,Lysén, Morten,Kehler, Jan,Kristensen, Jesper L.. "Ortho lithiation-in situ borylation of substituted morpholine benzamides". . p. 1576 - 1582. Retrieved 2017/03/08.