Formula C8H7N Density 1.02 g/cm³ Appearance Colorless oily liquid | Molar mass 117.15 g/mol Melting point -24 °C | |
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Benzyl cyanide (abbreviated BnCN) is an organic compound with the chemical formula C6H5CH2CN. This colorless oily aromatic liquid is an important precursor to numerous compounds in organic chemistry.
Contents
Preparation
Benzyl cyanide can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide and by oxidative decarboxylation of phenylalanine.
Chemical Properties
Benzyl cyanide can be hydrolyzed to give phenylacetic acid or used in the Pinner reaction to yield phenylacetic acid esters. The compound also forms an "active methylene unit" on the carbon between the aromatic ring and the nitrile functional group. This active carbon, referred to as a nitrile anion, is a useful reactive intermediate for 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 (phenethyl alcohol), antibiotics, and other pharmaceuticals.
Pharmaceuticals
Benzyl cyanide is a useful precursor to numerous pharmaceuticals. Examples include:
Regulation
Because benzyl cyanide is a useful precursor to numerous drugs with recreational use potential, many countries strictly regulate the compound.
United States
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. It is toxic and produces the deadly poison hydrogen cyanide when burned.
