Benzyl cyanide
Benzyl cyanide is an organic compound with the chemical formula C6H5CH2CN. This colorless oily aromatic liquid is an important precursor to numerous compounds in organic chemistry.Benzyl cyanide can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide and by oxidative decarboxylation of phenylalanine.
Benzyl cyanide undergoes many reactions characteristic of nitriles. Hydrolyzed gives phenylacetic acid or used in the Pinner reaction to yield phenylacetic acid esters. Hydrogenation gives β-phenethylamine.
The compound contains an "active methylene unit". Bromination occurs gives PhCHBrCN. A variety of base-induced reactions results in the formation of new carbon-carbon bonds.Uses
Benzyl cyanide is used as a solvent and as a starting material in the synthesis of fungicides, fragrances, antibiotics, and other pharmaceuticals. The partial hydrolysis of BnCN results in 2-phenylacetamide, a known anticonvulsant.Pharmaceuticals
Benzyl cyanide is a useful precursor to numerous pharmaceuticals. Examples include:
- Anorectics
- Analgesics
- Antiarrhythmics
- Antidepressants
- Antihistamines
- Antimalarial medications
- Antitussives
- Diuretics
- Hypnotics
- Spasmolytics
- Stimulants
- Azatadine
Regulation
Because benzyl cyanide is a useful precursor to numerous drugs with recreational use potential, many countries strictly regulate the compound.Benzyl cyanide is regulated in the United States as a DEA List I chemical.Safety
Benzyl cyanide, like related benzyl derivatives, is an irritant to the skin and eyes.
