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.<ref name=Ullmann>Template:Cite journal</ref>
Preparation
Benzyl cyanide can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide<ref>Template:Cite journal</ref> or by oxidative decarboxylation of phenylalanine.<ref>Template:Cite journal</ref>
Chemical Properties
Benzyl cyanide can be hydrolyzed to give Phenylacetic acid<ref>Template:Cite journal</ref> or can be used in the Pinner reaction to yield phenylacetic acid esters.<ref>Template:Cite journal</ref> 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.<ref>Template:Cite journal</ref><ref>Template:Cite journal</ref><ref>Template:Cite journal</ref>
Uses
Benzyl cyanide can be used as a solvent<ref>Template:Cite journal</ref> or as a starting material in the synthesis of other compounds such as fungicides,<ref>Template:Cite journal</ref> fragrances, antibiotics,<ref name=Ullmann></ref> or other pharmaceuticals.
Pharmaceuticals
Benzyl cyanide is a useful precursor to numerous pharmaceuticals. Examples include:
- Anorectics (e.g. sibutramine)<ref name=William>Template:Cite book</ref>
- Analgesics (e.g. ethoheptazine, ketobemidone, pethidine, and phenoperidine)<ref name=William></ref>
- Antiarrhythmics (e.g. disopyramide)<ref name=William></ref>
- Antidepressants (e.g. venlafaxine)<ref name=William></ref>
- Antihistamines (e.g. levocabastine and chlorphenamine)<ref name=William></ref><ref>Template:Cite journal</ref>
- Antimalarial medications (e.g. pyrimethamine)<ref name=William></ref>
- Antitussives (e.g. isoaminile, oxeladin, butethamate, pentapiperide, and pentoxyverine)<ref>Template:Cite journal</ref>
- Diuretics (e.g. triamterene)<ref>Template:Cite journal</ref>
- Hypnotics (e.g. alonimid and phenobarbital)<ref name=William></ref><ref name=Vogel>Template:Cite book</ref>
- Spasmolytics (e.g. pentapiperide and drofenine)<ref name=William></ref><ref>Template:Cite journal</ref>
- Stimulants (e.g. methylphenidate)<ref name=William></ref>
Regulation
Because benzyl cyanide is a useful precursor to numerous drugs with ***** potential, many countries strictly regulate the compound.
United States
Benzyl cyanide is regulated in the United States as a DEA List I chemical.
Safety
Benzyl cyanide, like related benzyl derivatives, is an irritant to the skin and eyes.<ref name=Ullmann/> It is toxic and produces hydrogen cyanide when burned.
References
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