1-Chloro-2-isocyanobenzene

Base Information

• Chemical Name: 1-Chloro-2-isocyanobenzene
• CAS No.: 10432-84-5
• Molecular Formula: C7H4ClN
• Molecular Weight: 137.568
• European Community (EC) Number: 858-676-5
• Nikkaji Number: J1.761.421E
• Mol file: 10432-84-5.mol

Synonyms:1-chloro-2-isocyanobenzene;10432-84-5;2-Chlorophenylisocyanide;2-chlorophenyl isocyanide;2-chlorophenyl-isonitrile;SCHEMBL653876;Benzene,1-chloro-2-isocyano-;DRNNMKBEVALIPU-UHFFFAOYSA-N;AC9402;MFCD02664596;AKOS006276917;GS-0315;SY069871;FT-0696909;EN300-254870

Chemical Property of 1-Chloro-2-isocyanobenzene

Chemical Property:

• Melting Point: 28-32 °C(lit.)
• Flash Point: 200 °F
• PSA: 0.00000
• LogP: 2.12150
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 137.0032268
• Heavy Atom Count: 9
• Complexity: 135

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Chloro-2-isocyanobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [C-]#[N+]C1=CC=CC=C1Cl

Technology Process of 1-Chloro-2-isocyanobenzene

There total 6 articles about 1-Chloro-2-isocyanobenzene 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: 94.0%

2-chloro-N-phenylformamide (2596-93-2) → 1-chloro-2-isocyanobenzene (10432-84-5)

Guidance literature:

With triethylamine; trichlorophosphate; In tetrahydrofuran; at 0 ℃; for 1.5h; Inert atmosphere;

DOI:10.1039/c9cc05655f

Reference yield: 51.0%

o-chlorophenylthiourea (5344-82-1) → 1-chloro-2-isocyanobenzene (10432-84-5) + (2-chlorophenyl)urea (114-38-5)

Guidance literature:

With cetyl-trimethylammonium dichromate; chemoselective reaction; Microwave irradiation;

DOI:10.1080/00397910903398684

Reference yield:

o-chloroaniline (95-51-2) → 1-chloro-2-isocyanobenzene (10432-84-5)

Guidance literature:

Multi-step reaction with 2 steps

1: zinc(II) oxide / neat (no solvent) / 70 °C

2: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 3.5 h / 40 °C / Molecular sieve

With bis(trichloromethyl) carbonate; triethylamine; zinc(II) oxide; In dichloromethane;

DOI:10.1016/j.ejmech.2015.03.069

upstream raw materials:

2-chloro-N-phenylformamide

2-chlorophenylisothiocyanate

o-chlorophenylthiourea

o-chloroaniline

Downstream raw materials:

[1-Aziridin-1-yl-meth-(Z)-ylidene]-(2-chloro-phenyl)-amine

(2-Chloro-phenyl)-[1-pyrrolidin-1-yl-meth-(Z)-ylidene]-amine

(2-Chloro-phenyl)-[1-piperidin-1-yl-meth-(Z)-ylidene]-amine

N,N-dimethyl-N'-(2-chlorophenyl)formamidine

Refernces

• 1、 Shingaki,Takebayashi. "". . p. 617. Retrieved 1963.
• 2、 Yuan, Yao,Dong, Wu-Heng,Gao, Xiao-Shuang,Xie, Xiao-Min,Zhang, Zhao-Guo. "Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: Synthesis of cyclopenta[: B] quinoxalines". supporting information. p. 11900 - 11903. Retrieved 2019/10/11.
• 3、 Hu, Zhongyan,Dong, Jinhuan,Men, Yang,Lin, Zhichen,Cai, Jinxiong,Xu, Xianxiu. "Silver-Catalyzed Chemoselective [4+2] Annulation of Two Isocyanides: A General Route to Pyridone-Fused Carbo- and Heterocycles". supporting information. p. 1805 - 1809. Retrieved 2017/02/05.