89883-07-8

Basic information

• Product Name: Benzeneacetonitrile, a-methylene-4-(2-methylpropyl)-
• CAS NO: 89883-07-8
• Molecular Formula: C13H15N
• Molecular Weight: 185.269
• Mol File: 89883-07-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzeneacetonitrile, a-methylene-4-(2-methylpropyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetonitrile, a-methylene-4-(2-methylpropyl)-(89883-07-8)
• EPA Substance Registry System: Benzeneacetonitrile, a-methylene-4-(2-methylpropyl)-(89883-07-8)

Safety Data

• Hazardous Substances Data: 89883-07-8(Hazardous Substances Data)

Upstream product

• 2942-58-7 diethyl cyanophosphonate 
• 38861-78-8 1-(4-isobutyl-phenyl)-ethanone 
• 58609-73-7 2-(4-isobutylphenyl)propanenitrile 
• 14906-59-3 4-cyanopyridine N-oxide 
• 132464-91-6 4'-isobutyl phenylacetylene 
• 7677-24-9 trimethylsilyl cyanide 
• 63444-56-4 p-isobutylstyrene 
• 63367-12-4 2-hydroxy-2-(4-iso-butylphenyl)propanenitrile 
• 952005-45-7 diphosphorus pentasulfide 

Downstream Products

• 15687-27-1 ibuprofen 

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.

Reduction of cyanohydrins

Arylacetonitriles corresponding to the formula Ar-CH(R)CN are prepared by reducing a cyanohydrin corresponding to the formula Ar-C(R)(OH)CN with phosphorus pentasulfide in an inert solvent; Ar in the formulas representing aryl and R being hydrogen or alkyl. The products are primarily useful as pharmaceutical and agricultural intermediates.