Benzyl cyanide

Benzyl cyanide

Names
IUPAC name 2-Phenylacetonitrile
Other names phenylacetonitrile, α-Tolunitrile, Benzylnitrile
Identifiers
CAS Number	140-29-4 Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:25979 Y
ChemSpider	13839308 Y
ECHA InfoCard	100.004.919
KEGG	C16074 Y
PubChem CID	8794
InChI InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2 Y Key: SUSQOBVLVYHIEX-UHFFFAOYSA-N Y InChI=1/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2 Key: SUSQOBVLVYHIEX-UHFFFAOYAJ
SMILES C1=CC=C(C=C1)CC#N c1ccc(cc1)CC#N
Properties
Chemical formula	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)
Magnetic susceptibility (χ)	-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).
Y  (what is YN ?)
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.

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

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.

Benzyl cyanide is used as a solvent and as a starting material in the synthesis of fungicides, fragrances (phenethyl alcohol), antibiotics, and other pharmaceuticals. The partial hydrolysis of BnCN results in 2-phenylacetamide, a known anticonvulsant.