Benzyl cyanide (abbreviated BnCN), also known as phenylacetonitrile, is an organic compound with the chemical formula C6H5CH2CN. This colorless oily aromatic liquid is an important precursor to numerous compounds in organic chemistry. It is also an important pheromone in certain species.
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: disopyramide), an antiarrhythmic milnacipran & lomevactone, antidepressants Antihistamines (e.g. levocabastine (para-fluoro), Pheniramine & Azatadine. Antitussives (e.g. isoaminile, oxeladin, fedrilate, pentoxyverine, etaminile, butethamate & pentapiperide) Diuretics (e.g. triamterene) Hypnotics (e.g. alonimid and phenobarbital) & Phenglutarimide Spasmolytics (e.g. pentapiperide, drofenine & dicycloverine) & Febuverine & Butetamate Stimulants (e.g. methylphenidate), mazindol & gamfexine & Levophacetoperane. Opioids (e.g. ethoheptazine, norpethidine, pethidine, properidine, phenoperidine). SERMs, e.g. Triphenylacrylonitrile [6304-33-2] (aka "TPAN") Fenclexonium (HOE-019) Benzetimide [14051-33-3] & Cinperene [14796-24-8] PyrroxanDaniel Lednicer & L.A. Mitscher drug synthesis Book 3, Page 191. MAOIs: 1-Phenylcyclobutylamine (PCBA) [17380-77-7]Silverman RB, Zieske PA. 1-Phenylcyclobutylamine, the first in a new class of monoamine oxidase inactivators. Further evidence for a radical intermediate. Biochemistry. 1986 Jan 28;25(2):341-6. doi: 10.1021/bi00350a010. PMID: 3955001.Singer, T.P. (1987). Perspectives in MAO: past, present, and future. In: Oreland, L., Callingham, B.A. (eds) Monoamine Oxidase Enzymes. Journal of Neural Transmission, vol 23. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8901-6_1 & 1-benzylcyclopropylamine.Karla Drescher, et al. WO2006040179 (2006 to Abbott GmbH and Co KG). Page column 97. PRE-084 Benzyl cyanide is used to make benzhydrylcyanide in Hoch's original procedure. This gives way to a large consortium of pharmaceuticals, c.f. methadone for example. Tolazoline
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 Bromobenzyl cyanide
References
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