2-Chlorobenzonitrile

Base Information

• Chemical Name: 2-Chlorobenzonitrile
• CAS No.: 873-32-5
• Molecular Formula: C7H4ClN
• Molecular Weight: 137.568
• Hs Code.: 29269095
• European Community (EC) Number: 212-836-5
• NSC Number: 8438
• DSSTox Substance ID: DTXSID5052593
• Nikkaji Number: J42.016F
• Wikipedia: 2-Chlorobenzonitrile
• Wikidata: Q72517239
• ChEMBL ID: CHEMBL3248211
• Mol file: 873-32-5.mol

Synonyms:2-chlorobenzonitrile

Chemical Property of 2-Chlorobenzonitrile

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.0577mmHg at 25°C
• Melting Point: 43-46 °C(lit.)
• Refractive Index: 1.563
• Boiling Point: 232.8 °C at 760 mmHg
• Flash Point: 100.8 °C
• PSA: 23.79000
• Density: 1.23 g/cm³
• LogP: 2.21168
• Storage Temp.: Store below +30°C.
• Solubility.: 1g/l
• 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:

99% ^*data from raw suppliers

2-Chlorobenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 21/22-36-21/22/23
• Safety Statements: 23

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C1=CC=C(C(=C1)C#N)Cl
• Uses: Intermediate for the synthesis of agrochemicals, pharmaceuticals and chemical intermediates. 2-Chlorobenzonitrile is mainly used in the synthesis of dye intermediates 2-cyano-4-nitroaniline, and in the pharmaceutical industry for the synthesis of new anti-malarial drugs such as nitroquine. 2-Chlorobenzonitrile is an activated aryl chloride that is commonly used in reactions that involve the Palladium-catalyzed direct arylation of heteroaromatics (e.g. 3-aminopicolinic acid [A627800]). 2-Chlorobenzonitrile and its substituted derivatives (e.g. 2,3-dichloro-6-nitrobenzonitrile [2112-22-3]) also have potential anti-inflammatory properties.

Technology Process of 2-Chlorobenzonitrile

There total 117 articles about 2-Chlorobenzonitrile 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%

2-chloro-benzaldehyde (89-98-5) → 2-Chlorobenzonitrile (873-32-5) + 2-chlorobenzamide (609-66-5)

Guidance literature:

With [Ru(η⁶-C₆Me₆)Cl₂(tris(dimethylamino)phosphine)]; hydroxylamine hydrochloride; sodium hydrogencarbonate; In water; at 100 ℃; for 7h; Inert atmosphere; Sealed tube; Green chemistry;

DOI:10.1039/c3ra23195j

Reference yield: 84.0%

2-chloro-benzamide oxime (56935-60-5) → 2-Chlorobenzonitrile (873-32-5) + 2-chlorobenzamide (609-66-5)

Guidance literature:

With tetraethylammonium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In acetonitrile; at 20 ℃; for 0.75h;

DOI:10.3998/ark.5550190.0011.209

Reference yield: 65.9%

2-CHLOROBENZYLAMINE (89-97-4) → 2-Chlorobenzonitrile (873-32-5) + 2-chlorobenzamide (609-66-5)

Guidance literature:

With ammonium hydroxide; oxygen; In tert-Amyl alcohol; at 110 ℃; for 16h; under 1500.15 Torr;

DOI:10.1039/c9cc06793k

upstream raw materials:

tetrachloromethane

ethanol

2-chlorobenzalchloroimine

salicylonitrile

Downstream raw materials:

2,3'-dichloro-benzophenone

1-(2-chlorophenyl)-2-phenyl-1-ethanone

Amino-1 ortho-chlorophenyl-1 (phenyl-2' quinoxalinyl-3')-2 ethene

Amino-1 ortho-chlorophenyl-1 (quinoxalinyl-2')-2 ethene

Refernces

• 1、 Hari Babu,Venkateswara Rao,Suh,Sai Prasad,Lingaiah. "One-step selective synthesis of 2-chlorobenzonitrile from 2-chlorotoluene: Via ammoxidation". . p. 1892 - 1901. Retrieved 2018.
• 2、 Niimi, Ryoko,Suzuka, Toshimasa,Uozumi, Yasuhiro. "Cyanide-Free Cyanation of Aryl Iodides with Nitromethane by Using an Amphiphilic Polymer-Supported Palladium Catalyst". supporting information. p. 40 - 44. Retrieved 2021/11/30.
• 3、 Wang, Wei David,Wang, Fushan,Chang, Youcai,Dong, Zhengping. "Biomass chitosan-derived nitrogen-doped carbon modified with iron oxide for the catalytic ammoxidation of aromatic aldehydes to aromatic nitriles". . . Retrieved 2020/11/24.