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

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

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

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.

Direct Access to Versatile Electrophiles via Catalytic Oxidative Cyanation of Alkenes

Nucleophilic attack on carbon-based electrophiles is a central reactivity paradigm in chemistry and biology. The steric and electronic properties of the electrophile dictate its reactivity with different nucleophiles of interest, allowing the opportunity to fine-tune electrophiles for use as coupling partners in multistep organic synthesis or for covalent modification of proteins in drug discovery. Reactions that directly transform inexpensive chemical feedstocks into versatile carbon electrophiles would therefore be highly enabling. Herein, we report the catalytic, regioselective oxidative cyanation of conjugated and nonconjugated alkenes using a homogeneous copper catalyst and a bystanding N-F oxidant to furnish branched alkenyl nitriles that are difficult to prepare using existing methods. We show that the alkenyl nitrile products serve as electrophilic reaction partners for both organic synthesis and the chemical proteomic discovery of covalent protein ligands.

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.

A NOVEL SYNTHESIS OF α,β-UNSATURATED NITRILES FROM AROMATIC KETONES VIA CYANOPHOSPHATES

Reaction of aromatic ketones with diethyl phosphorocyanidate in the presence of lithium cyanide gave cyanophosphates, which were converted into α,β-unsaturated nitriles by treatment with boron trifluoride etherate in high yields.