Pentanenitrile

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).

Pentanenitrile
Names
Other names
  • Valeronitrile
  • n-valeronitrile
  • 1-Cyanobutane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.439
EC Number
  • 203-781-8
UNII
UN number 3273
Properties
C5H9N
Molar mass 83.134 g·mol−1
Appearance Colorless liquid
Density 0.8008
Melting point −96.2 °C (−141.2 °F; 177.0 K)
Boiling point 141 °C; 286 °F; 414 K
Critical point (T, P) 610.3 K at 35.80 bar
insoluble
Solubility soluble in benzene, acetone, ether
Vapor pressure 5 mmHg
1.3949
Hazards
GHS pictograms
GHS Signal word Danger
H226, H301, H302
P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+310, P301+312, P303+361+353, P321, P330, P370+378, P403+235, P405, P501
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
3
0
Flash point 40 °C (104 °F; 313 K)
Lethal dose or concentration (LD, LC):
191 mg/kg fat[1]
Related compounds
Related alkanenitriles
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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%.[2]

Another way to get the substance is by heating valeraldehyde with hydroxylamine.[3]

Pentanenitrile is contained in bone oil.[4]

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.[5]

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.[1]

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]

References
  1. Buhler, D. R.; Reed, D. J. (2013). Nitrogen and Phosphorus Solvents. Elsevier. pp. 359–362. ISBN 9781483290201.
  2. Smiley, Robert; Arnold, Charles (February 1960). "Notes- Aliphatic Nitriles from Alkyl Chlorides". The Journal of Organic Chemistry. 25 (2): 257–258. doi:10.1021/jo01072a600.
  3. "Red mud catalyzed one-pot synthesis of nitriles from aldehydes and hydroxylamine hydrochloride under microwave irradiation". Arkivoc. 2007 (15): 162. 5 October 2007. doi:10.3998/ark.5550190.0008.f16.
  4. Toxic Substances Control Act (TSCA) Chemical Substance Inventory. the Office. 1979.
  5. Crowder, G.A. (October 1989). "Conformational analysis of n-butyl cyanide". Journal of Molecular Structure: THEOCHEM. 200: 235–244. doi:10.1016/0166-1280(89)85056-0.
  6. Gong, Jin-Song; Li, Heng; Zhu, Xiao-Yan; Lu, Zhen-Ming; Wu, Yan; Shi, Jing-Song; Xu, Zheng-Hong; Yun, Sung-Hwan (30 November 2012). "Fungal His-Tagged Nitrilase from Gibberella intermedia: Gene Cloning, Heterologous Expression and Biochemical Properties". PLOS ONE. 7 (11): e50622. doi:10.1371/journal.pone.0050622. PMC 3511519. PMID 23226336.
  7. Kaplan, Ondřej; Vejvoda, Vojtěch; Charvátová-Pišvejcová, Andrea; Martínková, Ludmila (15 August 2006). "Hyperinduction of nitrilases in filamentous fungi". Journal of Industrial Microbiology & Biotechnology. 33 (11): 891–896. doi:10.1007/s10295-006-0161-9. PMID 16909267. S2CID 3256514.
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