cyclohex-2-en-1-ylacetonitrile

Base Information

• Chemical Name: cyclohex-2-en-1-ylacetonitrile
• CAS No.: 82700-05-8
• Molecular Formula: C8H11N
• Molecular Weight: 121.182
• Mol file: 82700-05-8.mol

Synonyms:

Chemical Property of cyclohex-2-en-1-ylacetonitrile

Chemical Property:

• Vapor Pressure: 0.0918mmHg at 25°C
• Boiling Point: 224.3°Cat760mmHg
• Flash Point: 95.6°C
• Density: 0.927g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cyclohex-2-en-1-ylacetonitrile

There total 26 articles about cyclohex-2-en-1-ylacetonitrile 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: 86.0%

(E)-bicyclo[4.2.0]octan-7-one O-benzoyloxime → 2-(cyclohex-2-en-1-yl)acetonitrile (82700-05-8) + 2-methylenecyclohexanecarbonitrile

Guidance literature:

With potassium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; for 9h; Heating;

DOI:10.1021/jo049385k

Reference yield: 83.0%

(Z)-bicyclo[4.2.0]octan-7-one O-benzoyloxime → 2-(cyclohex-2-en-1-yl)acetonitrile (82700-05-8) + 2-methylenecyclohexanecarbonitrile

Guidance literature:

With potassium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In diethyl ether; for 72h; Heating;

DOI:10.1021/jo049385k

Reference yield: 60.0%

rac-3-bromocyclohexene (1521-51-3,113667-32-6) + acetonitrile (75-05-8,26809-02-9) → 2-(cyclohex-2-en-1-yl)acetonitrile (82700-05-8)

Guidance literature:

acetonitrile; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 1h; Inert atmosphere;

rac-3-bromocyclohexene; In tetrahydrofuran; hexane; at 0 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c03552

upstream raw materials:

cyano-cyclohex-1-enyl-acetic acid

1-iodo-2-cyclohexene

cyanomethyl bromide

cis-3-Methoxycyclohexanecarboxylic acid

Refernces

• 1、 Schreib, Benedikt S.,Carreira, Erick M.. "Palladium-Catalyzed Regioselective C-H Iodination of Unactivated Alkenes". supporting information. p. 8758 - 8763. Retrieved 2019/06/13.
• 2、 Lo, Kai-Yip,Ye, Liu,Yang, Dan. "Palladium-Catalyzed Aerobic Oxidative Cyclization of Aliphatic Alkenyl Amides for the Construction of Pyrrolizidine and Indolizidine Derivatives". supporting information. p. 1570 - 1575. Retrieved 2017/08/11.