Benzyl cyanide

Benzyl cyanide
Skeletal formula of benzyl cyanide
Ball-and-stick model of the benzyl cyanide molecule
Names
Preferred IUPAC name
Phenylacetonitrile
Other names
Benzyl cyanide
2-Phenylacetonitrile
α-Tolunitrile
Benzylnitrile
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.919 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2 checkY
    Key: SUSQOBVLVYHIEX-UHFFFAOYSA-N checkY
  • InChI=1/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2
    Key: SUSQOBVLVYHIEX-UHFFFAOYAJ
  • N#CCc1ccccc1
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).
checkY verify (what is checkY☒N ?)
Infobox references

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.

Preparation

Benzyl cyanide can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide and by oxidative decarboxylation of phenylalanine.

Benzyl cyanides can also be prepared by arylation of silyl-substituted acetonitrile.

Reactions

Benzyl cyanide undergoes many reactions characteristic of nitriles. It can be hydrolyzed to give phenylacetic acid or it can be 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 result 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 (.e.g. Fenapanil), fragrances (phenethyl alcohol), antibiotics, and other pharmaceuticals. The partial hydrolysis of BnCN results in 2-phenylacetamide.

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.

China

Benzyl cyanide is regulated in People's Republic of China as a Class III drug precursor since 7 June 2021.

Safety

Benzyl cyanide, like related benzyl derivatives, is an irritant to the skin and eyes.

See also


This page was last updated at 2023-04-01 05:47 UTC. Update now. View original page.

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