Pentanenitrile Explained

Pentanenitrile, valeronitrile or butyl cyanide is a nitrile with the formula C4H9CN. This can be written BuCN, with Bu representing an n-butyl (linear butyl group).

Production

Pentanenitrile can be produced by heating 1-chlorobutane with sodium cyanide in dimethyl sulfoxide. This reaction takes about 20 minutes, keeping the temperature below 160 °C. The yield is about 93%.[1]

Another way to get the substance is by heating valeraldehyde with hydroxylamine.[2]

Pentanenitrile is contained in bone oil.[3]

Properties

The pentanenitrile molecule is flexible and can adopt a number of different conformers, so that it will naturally be a mixture. These conformers are called anti-anti (30%), anti-gauche (46%), gauche-anti, gauche-gauche-cis, and gauche-gauche-trans.[4]

Biology

Pentanenitrile is toxic to animals, and produces its action by the liberation of cyanide by cytochrome P450. The cyanide is detoxified and excreted in urine as thiocyanate.[5]

Pentanenitrile is found in Brassica species and varieties such as broccoli.

Pentanenitrile is hydrolyzed to valeric acid by the fungi Gibberella intermedia,[6] Fusarium oxysporum, and Aspergillus niger in which it induces production of the nitrilase enzyme.[7]

Notes and References

  1. Smiley. Robert. Arnold. Charles. Notes- Aliphatic Nitriles from Alkyl Chlorides. The Journal of Organic Chemistry. February 1960. 25. 2. 257–258. 10.1021/jo01072a600.
  2. Red mud catalyzed one-pot synthesis of nitriles from aldehydes and hydroxylamine hydrochloride under microwave irradiation. Arkivoc. 5 October 2007. 2007. 15. 162–170. 10.3998/ark.5550190.0008.f16. free. Khezri. S. Hadi. Azimi. Nahal. Mohammed-Vali. Mehrdad. Eftekhari-Sis. Bagher. Hashemi. Mohammed M.. Baniasadi. Mohammed H.. Teimouri. Fatemeh. 2027/spo.5550190.0008.f16. free.
  3. Book: Toxic Substances Control Act (TSCA) Chemical Substance Inventory. 1979. the Office. en.
  4. Crowder. G.A.. Conformational analysis of n-butyl cyanide. Journal of Molecular Structure: THEOCHEM. October 1989. 200. 235–244. 10.1016/0166-1280(89)85056-0.
  5. Book: Buhler. D. R.. Reed. D. J.. Nitrogen and Phosphorus Solvents. 2013. Elsevier. 9781483290201. 359–362. en.
  6. Gong. Jin-Song. Li. Heng. Zhu. Xiao-Yan. Lu. Zhen-Ming. Wu. Yan. Shi. Jing-Song. Xu. Zheng-Hong. Yun. Sung-Hwan. Fungal His-Tagged Nitrilase from Gibberella intermedia: Gene Cloning, Heterologous Expression and Biochemical Properties. PLOS ONE. 30 November 2012. 7. 11. e50622. 10.1371/journal.pone.0050622. 23226336. 3511519. 2012PLoSO...750622G. free.
  7. Kaplan. Ondřej. Vejvoda. Vojtěch. Charvátová-Pišvejcová. Andrea. Martínková. Ludmila. Hyperinduction of nitrilases in filamentous fungi. Journal of Industrial Microbiology & Biotechnology. 15 August 2006. 33. 11. 891–896. 10.1007/s10295-006-0161-9. 16909267. 3256514. free.

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