2-Chlorobenzyl cyanide

Base Information

• Chemical Name: 2-Chlorobenzyl cyanide
• CAS No.: 2856-63-5
• Molecular Formula: C8H6ClN
• Molecular Weight: 151.595
• Hs Code.: 29269095
• European Community (EC) Number: 220-669-4
• NSC Number: 39462
• UNII: 3Y6ZL4BQ95
• DSSTox Substance ID: DTXSID40182773
• Nikkaji Number: J160K
• Wikidata: Q69757160
• Mol file: 2856-63-5.mol

Synonyms:2-Chlorobenzyl cyanide;2856-63-5;2-(2-chlorophenyl)acetonitrile;2-Chlorophenylacetonitrile;o-Chlorobenzyl cyanide;Benzeneacetonitrile, 2-chloro-;2-Chlorobenzeneacetonitrile;(2-Chlorophenyl)acetonitrile;Acetonitrile, (o-chlorophenyl)-;(o-Chlorophenyl)acetonitrile;o-Chlorophenylacetonitrile;2-chlorophenyl acetonitrile;3Y6ZL4BQ95;EINECS 220-669-4;NSC 39462;NSC-39462;2-chlorobenzylcyanide;2-chloro-phenyl-acetonitrile;UNII-3Y6ZL4BQ95;2-Chlorobenzyl cyanide, 97%;SCHEMBL1020369;(2-Chloro-phenyl)-acetonitrile;2-(2-chlorophenyl) acetonitrile;DTXSID40182773;NSC39462;STR01093;MFCD00001898;STK803140;AKOS000199192;CS-W020135;PS-5293;s12394;AC-10303;BP-13330;AM20050445;FT-0611999;EN300-17281;W-107041;Z56904744

Chemical Property of 2-Chlorobenzyl cyanide

Chemical Property:

• Appearance/Colour: clear slightly yellow liquid after melting
• Vapor Pressure: 0.0177mmHg at 25°C
• Melting Point: 21-24 °C
• Refractive Index: 1.5425-1.5445
• Boiling Point: 254 °C at 760 mmHg
• Flash Point: 107.7 °C
• PSA: 23.79000
• Density: 1.188 g/cm³
• LogP: 2.40608
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 151.0188769
• Heavy Atom Count: 10
• Complexity: 147

Purity/Quality:

≥99% ^*data from raw suppliers

2-Chlorobenzyl Cyanide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 36/37/38-23/24/25
• Safety Statements: 45-36/37/39-28B-26-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)CC#N)Cl
• Uses: 2-Chlorobenzyl cyanide was used in the synthesis of clopidogrel, platelet aggregation inhibitor.

Technology Process of 2-Chlorobenzyl cyanide

There total 15 articles about 2-Chlorobenzyl cyanide 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: 95.0%

sodium cyanide (773837-37-9) + 1-bromomethyl-2-chlorobenzene (611-17-6) → 2-Chlorophenylacetonitrile (2856-63-5)

Guidance literature:

In water; at 30 ℃; for 48h; Green chemistry;

DOI:10.1021/acs.joc.7b01679

Reference yield: 91.0%

sodium cyanide (143-33-9,25596-52-5) + 1-chloro-2-(chloromethyl)benzene (611-19-8) → 2-Chlorophenylacetonitrile (2856-63-5)

Guidance literature:

DOI:10.1002/1522-2675(200207)85:7<2089::AID-HLCA2089>3.0.CO;2-0

Reference yield: 90.0%

3-(2-chloro-phenyl)-2-hydroxyimino-propionic acid (139109-52-7) → 2-Chlorophenylacetonitrile (2856-63-5)

Guidance literature:

With 1,1'-carbonyldiimidazole; In benzene; 1.) r.t., 15 min, 2.) 68-70 deg C, 1 h;

DOI:10.1248/cpb.39.3030

upstream raw materials:

3-(2-chloro-phenyl)-2-hydroxyimino-propionic acid

acetic anhydride

sodium cyanide

1-chloro-2-(chloromethyl)benzene

Downstream raw materials:

(2-chloro-phenyl)-[2]pyridyl-acetonitrile

1-chloro-2-(nitromethyl)benzene

2-chlorophenylacetic acid ethyl ester

5-(2-chloro-phenyl)-pyrimidin-4-ylamine

Refernces

• 1、 Sela, Tal,Lin, Xiaoxi,Vigalok, Arkadi. "Concentrated Aqueous Sodium Tosylate as Green Medium for Alkene Oxidation and Nucleophilic Substitution Reactions". . p. 11609 - 11612. Retrieved 2017/11/10.
• 2、 Tseng, Kuei-Nin T.,Rizzi, Andrew M.,Szymczak, Nathaniel K.. "Oxidant-free conversion of primary amines to nitriles". supporting information. p. 16352 - 16355. Retrieved 2013/12/04.