Names | |
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Preferred IUPAC name
Phenylacetonitrile[1] | |
Other names | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.004.919 |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C8H7N | |
Molar mass | 117.15 g/mol |
Appearance | Colorless oily liquid |
Density | 1.015 g/cm3 |
Melting point | −24 °C (−11 °F; 249 K) |
Boiling point | 233 to 234 °C (451 to 453 °F; 506 to 507 K) |
-76.87·10−6 cm3/mol | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[2] It is also an important pheromone in certain species.[3]
Benzyl cyanide can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide[4] and by oxidative decarboxylation of phenylalanine.[5]
Benzyl cyanides can also be prepared by arylation of silyl-substituted acetonitrile.[6]
Benzyl cyanide undergoes many reactions characteristic of nitriles. It can be hydrolyzed to give phenylacetic acid[7] or it can be used in the Pinner reaction to yield phenylacetic acid esters.[8] Hydrogenation gives β-phenethylamine.[9]
The compound contains an "active methylene unit". Bromination occurs gives PhCHBrCN.[10] A variety of base-induced reactions result in the formation of new carbon-carbon bonds.[11][12][13]
Benzyl cyanide is used as a solvent[14] and as a starting material in the synthesis of fungicides (.e.g. Fenapanil),[15] fragrances (phenethyl alcohol), antibiotics,[2] and other pharmaceuticals. The partial hydrolysis of BnCN results in 2-phenylacetamide.[16]
Benzyl cyanide is a useful precursor to numerous pharmaceuticals. Examples include: [17]
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.
Benzyl cyanide is regulated in People's Republic of China as a Class III drug precursor since 7 June 2021.[23]
Benzyl cyanide, like related benzyl derivatives, is an irritant to the skin and eyes.[2]