106595-22-6

Basic information

• Product Name: 2,3c-bis-(3-chloro-phenyl)-acrylonitrile
• Synonyms: 2,3c-bis-(3-chloro-phenyl)-acrylonitrile
• CAS NO: 106595-22-6
• Molecular Weight: 274.149
• Mol File: 106595-22-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,3c-bis-(3-chloro-phenyl)-acrylonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3c-bis-(3-chloro-phenyl)-acrylonitrile(106595-22-6)
• EPA Substance Registry System: 2,3c-bis-(3-chloro-phenyl)-acrylonitrile(106595-22-6)

Safety Data

• Hazardous Substances Data: 106595-22-6(Hazardous Substances Data)

Upstream product

• 14906-59-3 4-cyanopyridine N-oxide 
• 5216-30-8 1,2-bis(3-chlorophenyl)ethyne 
• 1529-41-5 3-chloro-benzeneacetonitrile 
• 587-04-2 m-Chlorobenzaldehyde 

Relevant articles and documents

Nickel-Catalyzed Cyanation of Aryl Halides and Hydrocyanation of Alkynes via C-CN Bond Cleavage and Cyano Transfer

We report nickel-catalyzed cyanation and hydrocyanation methods to prepare aryl nitriles and vinyl nitriles from aryl halides and alkynes, respectively. Using inexpensive and nontoxic 4-cyanopyridine N-oxide as the cyano shuttle, the methods provide an efficient approach to prepare aryl cyanides and vinyl nitriles under mild and operationally simple reaction conditions with a broad range of functional group tolerances. In hydrocyanation of alkynes, the method demonstrated good regioselectivity, producing predominantly E- or Z-alkenyl nitriles in a controlled manner and exclusively Markovnikov vinyl nitriles when internal diaryl alkynes and terminal alkynes were applied as the substrates, respectively. The preliminary mechanistic investigation indicated that the C-CN bond cleavage process is promoted by oxidative addition to the nickel(I) complex in the cyanation of aryl halides, and further studies via a series of deuterium exchange experiments indicated that water serves as the hydrogen source for the hydrocyanation of alkynes.