Benzyl cyanide
Skeletal formula of benzyl cyanide
Ball-and-stick model of the benzyl cyanide molecule
Names
Preferred IUPAC name
Phenylacetonitrile[1]
Other names
Benzyl cyanide[1]
2-Phenylacetonitrile
α-Tolunitrile
Benzylnitrile
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.919
KEGG
UNII
  • InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2 checkY
    Key: SUSQOBVLVYHIEX-UHFFFAOYSA-N checkY
  • InChI=1/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2
    Key: SUSQOBVLVYHIEX-UHFFFAOYAJ
  • N#CCc1ccccc1
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)
-76.87·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
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.[2] It is also an important pheromone in certain species.[3]

Preparation

Benzyl cyanide can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide[4] and by oxidative decarboxylation of phenylalanine.[5]

Benzyl cyanides can also be prepared by arylation of silyl-substituted acetonitrile.[6]

Reactions

Benzyl cyanide undergoes many reactions characteristic of nitriles. It can be hydrolyzed to give phenylacetic acid[7] or it can be used in the Pinner reaction to yield phenylacetic acid esters.[8] Hydrogenation gives β-phenethylamine.[9]

The compound contains an "active methylene unit". Bromination occurs gives PhCHBrCN.[10] A variety of base-induced reactions result in the formation of new carbon-carbon bonds.[11][12][13]

Uses

Benzyl cyanide is used as a solvent[14] and as a starting material in the synthesis of fungicides (.e.g. Fenapanil),[15] fragrances (phenethyl alcohol), antibiotics,[2] and other pharmaceuticals. The partial hydrolysis of BnCN results in 2-phenylacetamide.[16]

Pharmaceuticals

Benzyl cyanide is a useful precursor to numerous pharmaceuticals. Examples include: [17]

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.[23]

Safety

Benzyl cyanide, like related benzyl derivatives, is an irritant to the skin and eyes.[2]

See also

References

  1. 1 2 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 16. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. 1 2 3 Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2000). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a17_363. ISBN 3527306730.
  3. ↑ https://www.mpg.de/20278575/0504-choe-chemisches-signal-schuetzt-wanderheuschrecken-vor-kannibalismus
  4. ↑ Adams, Roger; Thal, A. F. (1922). "Benzyl cyanide". Organic Syntheses. 2: 9. doi:10.15227/orgsyn.002.0009.
  5. ↑ Hiegel, Gene; Lewis, Justin; Bae, Jason (2004). "Conversion of α‐Amino Acids into Nitriles by Oxidative Decarboxylation with Trichloroisocyanuric Acid". Synthetic Communications. 34 (19): 3449–3453. doi:10.1081/SCC-200030958. S2CID 52208189.
  6. ↑ Wu, Lingyun; Hartwig, John F. (2005). "Mild Palladium-Catalyzed Selective Monoarylation of Nitriles". Journal of the American Chemical Society. 127 (45): 15824–15832. doi:10.1021/ja053027x. PMID 16277525.
  7. ↑ Adams, Roger; Thal, A. F. (1922). "Phenylacetic acid". Organic Syntheses. 2: 59. doi:10.15227/orgsyn.002.0059.
  8. ↑ Adams, Roger; Thal, A. F. (1922). "Ethyl Phenylacetate". Organic Syntheses. 2: 27. doi:10.15227/orgsyn.002.0027.
  9. ↑ Robinson, John C. Jr.; Snyder, H. R. (1943). "β-Phenylethylamine". Organic Syntheses. 23: 71. doi:10.15227/orgsyn.023.0071.
  10. ↑ Robb, C. M.; Schultz, E. M. (1948). "Diphenylacetonitrile". Organic Syntheses. 28: 55. doi:10.15227/orgsyn.028.0055.
  11. ↑ Makosza, M.; Jonczyk, A (1976). "Phase-Transfer Alkylation of Nitriles: 2-Phenylbutyronitrile". Organic Syntheses. 55: 91. doi:10.15227/orgsyn.055.0091.
  12. ↑ Itoh, Masumi; Hagiwara, Daijiro; Kamiya, Takashi (1988). "New Reagent for tert-Butoxycarbonylation: 2-tert-Butoxycarbonyloxyimino-2-phenylacetonitrile". Organic Syntheses. 6: 199. doi:10.15227/orgsyn.059.0095.
  13. ↑ Wawzonek, Stanley; Smolin, Edwin M. (1955). "α-Phenylcinnamonitrile". Organic Syntheses. 3: 715. doi:10.15227/orgsyn.029.0083.
  14. ↑ Bien, Hans-Samuel; Stawitz, Josef; Wunderlich, Klaus (2000). "Anthraquinone Dyes and Intermediates". Ullmann's Encyclopedia of Industrial Chemistry: 29. doi:10.1002/14356007.a02_355. ISBN 3527306730.
  15. ↑ Ackermann, Peter; Margot, Paul; Müller, Franz (2000). "Fungicides, Agricultural". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a12_085. ISBN 3527306730.
  16. ↑ "PHENYLACETAMIDE". Organic Syntheses. 32: 92. 1952. doi:10.15227/orgsyn.032.0092. ISSN 0078-6209.
  17. 1 2 3 4 5 6 7 William Andrew Publishing (2008). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Norwich, NY: Elsevier Science. pp. 182, 936, 1362, 1369, 1505, 2036, 2157, 2259, 2554, 2620, 2660, 2670, 2924, 3032, & 3410. ISBN 9780815515265.
  18. ↑ Berkoff, Charles E.; Rivard, Donald E.; Kirkpatrick, David; Ives, Jeffrey L. (1980). "The Reductive Decyanation of Nitriles by Alkali Fusion". Synthetic Communications. 10 (12): 939–945. doi:10.1080/00397918008061855.
  19. ↑ Bub, Oskar; Friedrich, Ludwig (2000). "Cough Remedies". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_013. ISBN 3527306730.
  20. ↑ Hropot, Max; Lang, Hans-Jochen (2000). "Diuretics". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a09_029. ISBN 3527306730.
  21. ↑ Furniss, Brian; Hannaford, Antony; Smith, Peter & Tatchell, Austin (1996). Vogel's Textbook of Practical Organic Chemistry 5th Ed. London: Longman Science & Technical. pp. 1174–1179. ISBN 9780582462366.
  22. ↑ Bungardt, Edwin; Mutschler, Ernst (2000). "Spasmolytics". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a24_515. ISBN 3527306730.
  23. ↑ "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" (in Simplified Chinese). The State Council - The People's Republic of China. 7 June 2021. Retrieved 11 October 2021.
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