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
Preferred IUPAC name Pentanenitrile
Other names Valeronitrile n-valeronitrile 1-Cyanobutane
Identifiers
CAS Number	110-59-8 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1503158
ChemSpider	7770 N
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 N Key: RFFFKMOABOFIDF-UHFFFAOYSA-N 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

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]