Pentanenitrile
Names
Preferred IUPAC name
Other names
Valeronitrile n -valeronitrile1-Cyanobutane
Identifiers
ChEMBL
ChemSpider
ECHA InfoCard 100.003.439
EC Number
UNII
UN number
3273
InChI=1S/C5H9N/c1-2-3-4-5-6/h2-4H2,1H3
N Key: RFFFKMOABOFIDF-UHFFFAOYSA-N
N
Properties
C 5 H 9 N
Molar mass
−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 labelling
Danger
H226 , H301 , H302
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
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).
Chemical compound
Pentanenitrile , valeronitrile or butyl cyanide is a nitrile with the formula C4 H9 CN. 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%.[ 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
Pentanenitrile is hydrolyzed to valeric acid by the fungi Gibberella intermedia [ 6] Fusarium oxysporum Aspergillus niger nitrilase enzyme.[ 7]
References
^ a b Buhler, D. R.; Reed, D. J. (2013). Nitrogen and Phosphorus Solvents 359– 362. ISBN 9781483290201 ^ 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 . ^ 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 ^ Toxic Substances Control Act (TSCA) Chemical Substance Inventory ^ 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 . ^ 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 . ^ 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 .
