![]() | |
Names | |
---|---|
Preferred IUPAC name
Pentanenitrile | |
Other names
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.439 |
EC Number |
|
PubChem
CID
|
|
UNII | |
UN number | 3273 |
CompTox Dashboard (
EPA)
|
|
| |
| |
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 |
Refractive index (nD)
|
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 (fire diamond) | |
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
|
|
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
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 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]
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]
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]