Pentanenitrile

Pentanenitrile
Names
	Preferred IUPAC name Pentanenitrile
	Other names Valeronitrile; n-valeronitrile; 1-Cyanobutane;
Identifiers
CAS Number	110-59-8 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1503158;
ChemSpider	7770 ;
ECHA InfoCard	100.003.439
EC Number	203-781-8;
PubChem CID	8061;
UNII	X44H3R47D4;
UN number	3273
CompTox Dashboard (EPA)	DTXSID3026275 ;
	InChI InChI=1S/C5H9N/c1-2-3-4-5-6/h2-4H2,1H3 Key: RFFFKMOABOFIDF-UHFFFAOYSA-N ;
	SMILES CCCCC#N;
Properties
Chemical formula	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
Solubility in water	insoluble
Solubility	soluble in benzene, acetone, ether
Vapor pressure	5 mmHg
Refractive index (nD)	1.3949
Hazards
	GHS labelling:
Pictograms
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)	3 3 0
Flash point	40 °C (104 °F; 313 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	191 mg/kg fat[1]
Related compounds
Related alkanenitriles	Isobutyronitrile; Propanenitrile; Malononitrile; Pivalonitrile; Succinonitrile; Glutaronitrile; Butyronitrile;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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%.[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

Buhler, D. R.; Reed, D. J. (2013). Nitrogen and Phosphorus Solvents. Elsevier. pp. 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.
Toxic Substances Control Act (TSCA) Chemical Substance Inventory. the Office. 1979.
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.

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[buhl-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.

[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.

[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.