Benzyl cyanide explained

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, 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]

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

External links

Notes and References

  1. Pollak. Peter. Romeder. Gérard. Hagedorn. Ferdinand. Gelbke. Heinz-Peter. Nitriles. Ullmann's Encyclopedia of Industrial Chemistry. 2000. 10.1002/14356007.a17_363. 3527306730.
  2. https://www.mpg.de/20278575/0504-choe-chemisches-signal-schuetzt-wanderheuschrecken-vor-kannibalismus
  3. Adams. Roger. Thal. A. F.. Benzyl cyanide. Organic Syntheses. 1922. 2. 9. 10.15227/orgsyn.002.0009.
  4. Hiegel. Gene. Lewis. Justin. Bae. Jason. Conversion of α‐Amino Acids into Nitriles by Oxidative Decarboxylation with Trichloroisocyanuric Acid. Synthetic Communications. 2004. 34. 19. 3449–3453. 10.1081/SCC-200030958. 52208189.
  5. 10.1021/ja053027x. Mild Palladium-Catalyzed Selective Monoarylation of Nitriles. 2005. Wu. Lingyun. Hartwig. John F.. Journal of the American Chemical Society. 127. 45. 15824–15832. 16277525.
  6. Adams. Roger. Thal. A. F.. Phenylacetic acid. Organic Syntheses. 1922. 2. 59. 10.15227/orgsyn.002.0059.
  7. Adams. Roger. Thal. A. F.. Ethyl Phenylacetate. Organic Syntheses. 1922. 2. 27. 10.15227/orgsyn.002.0027.
  8. 10.15227/orgsyn.023.0071. β-Phenylethylamine. Organic Syntheses. 1943. 23. 71. John C. Jr.. Robinson. H. R.. Snyder.
  9. C. M.. Robb. E. M.. Schultz. 10.15227/orgsyn.028.0055. Diphenylacetonitrile. Organic Syntheses. 1948. 28. 55.
  10. Makosza. M.. Jonczyk. A. Phase-Transfer Alkylation of Nitriles: 2-Phenylbutyronitrile. Organic Syntheses. 1976. 55. 91. 10.15227/orgsyn.055.0091.
  11. Itoh. Masumi. Hagiwara. Daijiro. Kamiya. Takashi. New Reagent for tert-Butoxycarbonylation: 2-tert-Butoxycarbonyloxyimino-2-phenylacetonitrile. Organic Syntheses. 1988. 6. 199. 10.15227/orgsyn.059.0095.
  12. Wawzonek. Stanley. Smolin. Edwin M.. α-Phenylcinnamonitrile. Organic Syntheses. 1955. 3. 715. 10.15227/orgsyn.029.0083.
  13. Bien. Hans-Samuel. Stawitz. Josef. Wunderlich. Klaus. Anthraquinone Dyes and Intermediates. Ullmann's Encyclopedia of Industrial Chemistry. 2000. 29. 10.1002/14356007.a02_355. 3527306730.
  14. Ackermann. Peter. Margot. Paul. Müller. Franz. Fungicides, Agricultural. Ullmann's Encyclopedia of Industrial Chemistry. 2000. 10.1002/14356007.a12_085. 3527306730.
  15. PHENYLACETAMIDE. Organic Syntheses. 32. 1952. 92. 0078-6209. 10.15227/orgsyn.032.0092.
  16. Book: William Andrew Publishing. Pharmaceutical Manufacturing Encyclopedia. 2008. Elsevier Science. Norwich, NY. 9780815515265. 182, 936, 1362, 1369, 1505, 2036, 2157, 2259, 2554, 2620, 2660, 2670, 2924, 3032, & 3410. 3rd.
  17. Berkoff. Charles E.. Rivard. Donald E.. Kirkpatrick. David. Ives. Jeffrey L.. The Reductive Decyanation of Nitriles by Alkali Fusion. Synthetic Communications. 1980. 10. 12. 939–945. 10.1080/00397918008061855.
  18. Bub. Oskar. Friedrich. Ludwig. Cough Remedies. Ullmann's Encyclopedia of Industrial Chemistry. 2000. 10.1002/14356007.a08_013. 3527306730.
  19. Hropot. Max. Lang. Hans-Jochen. Diuretics. Ullmann's Encyclopedia of Industrial Chemistry. 2000. 10.1002/14356007.a09_029. 3527306730.
  20. Book: Furniss, Brian . Hannaford, Antony . Smith, Peter . Tatchell, Austin . amp . Vogel's Textbook of Practical Organic Chemistry 5th Ed.. 1996. Longman Science & Technical. London. 9780582462366. 1174–1179.
  21. Bungardt. Edwin. Mutschler. Ernst. Spasmolytics. Ullmann's Encyclopedia of Industrial Chemistry. 2000. 10.1002/14356007.a24_515. 3527306730.
  22. Web site: 国务院办公厅关于同意将α-苯乙酰乙酸甲酯等6种物质列入易制毒化学品品种目录的函. The State Council - The People's Republic of China. zh-hans. 7 June 2021. 11 October 2021.

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