Benzyl cyanide

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.^[3] It is also an important pheromone in certain species.^[4]

Benzyl cyanide

Names
Preferred IUPAC name Phenylacetonitrile[1]
Other names Benzyl cyanide[1] 2-Phenylacetonitrile α-Tolunitrile Benzylnitrile
Identifiers
CAS Number	140-29-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:25979 Y
ChemSpider	13839308 Y
ECHA InfoCard	100.004.919
KEGG	C16074 Y
PubChem CID	8794
UNII	23G40PRP93 Y
CompTox Dashboard (EPA)	DTXSID2021492
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 N#CCc1ccccc1
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
Hazards[2]
Occupational safety and health (OHS/OSH):
Main hazards	Poisonous. May be fatal if inhaled, swallowed, or absorbed through skin. Contact may cause burns to skin and eyes.
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H302, H311, H330
Precautionary statements	P260, P262, P264, P270, P271, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, P501
NFPA 704 (fire diamond)	3 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Preparation

Benzyl cyanide can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide^[5] and by oxidative decarboxylation of phenylalanine.^[6]

Benzyl cyanides can also be prepared by arylation of silyl-substituted acetonitrile.^[7]

Reactions

Benzyl cyanide undergoes many reactions characteristic of nitriles. It can be hydrolyzed to give phenylacetic acid^[8] or it can be used in the Pinner reaction to yield phenylacetic acid esters.^[9] Hydrogenation gives β-phenethylamine.^[10]

The compound contains an "active methylene unit". Bromination occurs gives PhCHBrCN.^[11] A variety of base-induced reactions result in the formation of new carbon-carbon bonds.^[12][13][14]

Uses

Benzyl cyanide is used as a solvent^[15] and as a starting material in the synthesis of fungicides (e.g. Fenapanil),^[16] fragrances (phenethyl alcohol), antibiotics,^[3] and other pharmaceuticals. The partial hydrolysis of BnCN results in 2-phenylacetamide.^[17]

Pharmaceuticals

Benzyl cyanide is a useful precursor to numerous pharmaceuticals. Examples include: ^[18]

• Antiarrhythmics (e.g. disopyramide)^[18]
• Antidepressants: E.g. Milnacipran & Lomevactone
• Antihistamines (e.g. levocabastine (para-fluoro),^[18][19] Pheniramine & Azatadine.
• Antitussives (e.g. isoaminile, oxeladin, butethamate, pentapiperide, and pentoxyverine)^[20]
• Diuretics (e.g. triamterene)^[21]
• Hypnotics (e.g. alonimid and phenobarbital)^[18][22] & Phenglutarimide
• Spasmolytics (e.g. pentapiperide and drofenine)^[18][23]
• Stimulants (e.g. methylphenidate),^[18] mazindol & gamfexine.
• Opioids (e.g. ethoheptazine, pethidine, and phenoperidine)^[18] & methadone

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.^[24]

Safety

Benzyl cyanide, like related benzyl derivatives, is an irritant to the skin and eyes.^[3]

See also

• Bromobenzyl cyanide