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Pentanenitrile

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Pentanenitrile
Names
Preferred IUPAC name Pentanenitrile
Other names
  • Valeronitrile
  • n-valeronitrile
  • 1-Cyanobutane
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.439 Edit this at Wikidata
EC Number
  • 203-781-8
PubChem CID
UNII
UN number 3273
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H9N/c1-2-3-4-5-6/h2-4H2,1H3Key: RFFFKMOABOFIDF-UHFFFAOYSA-N
SMILES
  • CCCCC#N
Properties
Chemical formula C5H9N
Molar mass 83.134 g·mol
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
Solubility in water insoluble
Solubility soluble in benzene, acetone, ether
Vapor pressure 5 mmHg
Refractive index (nD) 1.3949
Hazards
GHS labelling:
Pictograms GHS02: Flammable GHS06: ToxicGHS07: Exclamation mark
Signal word Danger
Hazard statements H226, H301, H302
Precautionary statements P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P310, P301+P312, P303+P361+P353, P321, P330, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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. gasolineInstability 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):
LD50 (median dose) 191 mg/kg fat
Related compounds
Related alkanenitriles
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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%.

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

Pentanenitrile is contained in bone oil.

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.

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.

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

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

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. Khezri, S. Hadi; Azimi, Nahal; Mohammed-Vali, Mehrdad; Eftekhari-Sis, Bagher; Hashemi, Mohammed M.; Baniasadi, Mohammed H.; Teimouri, Fatemeh (5 October 2007). "Red mud catalyzed one-pot synthesis of nitriles from aldehydes and hydroxylamine hydrochloride under microwave irradiation". Arkivoc. 2007 (15): 162–170. doi:10.3998/ark.5550190.0008.f16. hdl:2027/spo.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. Bibcode:2012PLoSO...750622G. doi:10.1371/journal.pone.0050622. PMC 3511519. PMID 23226336.Open access icon
  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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