Английская Википедия: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.[1] It is also an important pheromone in certain species.[2]
Preparation
Benzyl cyanide can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide[3] and by oxidative decarboxylation of phenylalanine.[4]
Benzyl cyanides can also be prepared by arylation of silyl-substituted acetonitrile.[5]
Reactions
Benzyl cyanide undergoes many reactions characteristic of nitriles. It can be hydrolyzed to give phenylacetic acid[6] or it can be used in the Pinner reaction to yield phenylacetic acid esters.[7] Hydrogenation gives β-phenethylamine.[8]
The compound contains an "active methylene unit". Bromination occurs gives PhCHBrCN.[9] A variety of base-induced reactions result in the formation of new carbon-carbon bonds.[10][11][12]
Uses
Benzyl cyanide is used as a solvent[13] and as a starting material in the synthesis of fungicides (.e.g. Fenapanil),[14] fragrances (phenethyl alcohol), antibiotics,[1] and other pharmaceuticals. The partial hydrolysis of BnCN results in 2-phenylacetamide.[15]
Pharmaceuticals
Benzyl cyanide is a useful precursor to numerous pharmaceuticals. Examples include: [16]
- Antiarrhythmics (e.g. disopyramide)[16]
- Antidepressants: E.g. Milnacipran & Lomevactone
- Antihistamines (e.g. levocabastine (para-fluoro),[16][17] Pheniramine & Azatadine.
- Antitussives (e.g. isoaminile, oxeladin, butethamate, pentapiperide, and pentoxyverine)[18]
- Diuretics (e.g. triamterene)[19]
- Hypnotics (e.g. alonimid and phenobarbital)[16][20] & Phenglutarimide
- Spasmolytics (e.g. pentapiperide and drofenine)[16][21]
- Stimulants (e.g. methylphenidate)[16]
- Opioids (e.g. ethoheptazine, pethidine, and phenoperidine)[16] & 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.[22]
Safety
Benzyl cyanide, like related benzyl derivatives, is an irritant to the skin and eyes.[1]
See also
References
External links
- ↑ 1,0 1,1 1,2 Шаблон:Cite journal
- ↑ https://www.mpg.de/20278575/0504-choe-chemisches-signal-schuetzt-wanderheuschrecken-vor-kannibalismus
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
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- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ 16,0 16,1 16,2 16,3 16,4 16,5 16,6 Шаблон:Cite book
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite book
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite web
