Benzyl cyanide
| Skeletal formula of benzyl cyanide | |
| Ball-and-stick model of the benzyl cyanide molecule | |
| Names | |
|---|---|
| IUPAC name
2-Phenylacetonitrile
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| Other names
phenylacetonitrile, α-Tolunitrile
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| Identifiers | |
140-29-4  |
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| ChEBI | CHEBI:25979 |
| ChemSpider | 13839308 |
| Jmol 3D model | Interactive image Interactive image |
| KEGG | C16074 |
| PubChem | 8794 |
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| 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) |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| 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.[1]
Contents
Preparation
Benzyl cyanide can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide[2] or by oxidative decarboxylation of phenylalanine.[3]
Chemical Properties
Benzyl cyanide can be hydrolyzed to give Phenylacetic acid[4] or can be used in the Pinner reaction to yield phenylacetic acid esters.[5] 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.[6][7][8]
Uses
Benzyl cyanide can be used as a solvent[9] or as a starting material in the synthesis of other compounds such as fungicides,[10] fragrances, antibiotics,[1] or other pharmaceuticals.
Pharmaceuticals
Benzyl cyanide is a useful precursor to numerous pharmaceuticals. Examples include:
- Anorectics (e.g. sibutramine)[11]
- Analgesics (e.g. ethoheptazine, ketobemidone, pethidine, and phenoperidine)[11]
- Antiarrhythmics (e.g. disopyramide)[11]
- Antidepressants (e.g. venlafaxine)[11]
- Antihistamines (e.g. levocabastine and chlorphenamine)[11][12]
- Antimalarial medications (e.g. pyrimethamine)[11]
- Antitussives (e.g. isoaminile, oxeladin, butethamate, pentapiperide, and pentoxyverine)[13]
- Diuretics (e.g. triamterene)[14]
- Hypnotics (e.g. alonimid and phenobarbital)[11][15]
- Spasmolytics (e.g. pentapiperide and drofenine)[11][16]
- Stimulants (e.g. methylphenidate)[11]
Regulation
Because benzyl cyanide is a useful precursor to numerous drugs with abuse 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.[1] It is toxic and produces hydrogen cyanide when burned.
References
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- ↑ 11.0 11.1 11.2 11.3 11.4 11.5 11.6 11.7 11.8 Lua error in package.lua at line 80: module 'strict' not found.
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External links
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