Pentanenitrile, valeronitrile or butyl cyanide is a

nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix ''cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including met ...

with the formula C₄H₉CN. This can be written BuCN, with Bu representing an ''n''-butyl (linear

butyl group In organic chemistry, butyl is a four-carbon alkyl radical or substituent group with general chemical formula , derived from either of the two isomers (''n''-butane and isobutane) of butane. The isomer ''n''-butane can connect in two ways, givi ...

Production

Pentanenitrile can be produced by heating 1-chlorobutane with

sodium cyanide Sodium cyanide is a poisonous compound with the formula Na C N. It is a white, water-soluble solid. Cyanide has a high affinity for metals, which leads to the high toxicity of this salt. Its main application, in gold mining, also exploits its hi ...

dimethyl sulfoxide Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula ( CH3)2. This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds a ...

. 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 Pentanal (also called valeraldehyde) is the organic compound is an alkyl aldehyde, molecular formula C5H10O. It is used in flavorings, resin chemistry, and rubber accelerators. Its smell is described as fermented, bready, fruity, nutty, berry. ...

with

hydroxylamine Hydroxylamine is an inorganic compound with the formula . The material is a white crystalline, hygroscopic compound.Greenwood and Earnshaw. ''Chemistry of the Elements.'' 2nd Edition. Reed Educational and Professional Publishing Ltd. pp. 431–43 ...

. 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 Cytochromes P450 (CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that functions as monooxygenases. In mammals, these proteins oxidize steroids, fatty acids, and xenobiotics, and are ...

. The cyanide is detoxified and excreted in urine as

thiocyanate Thiocyanate (also known as rhodanide) is the anion . It is the conjugate base of thiocyanic acid. Common derivatives include the colourless salts potassium thiocyanate and sodium thiocyanate. Mercury(II) thiocyanate was formerly used in pyrot ...

. Pentanenitrile is found in ''

Brassica ''Brassica'' () is a genus of plants in the cabbage and mustard family (Brassicaceae). The members of the genus are informally known as cruciferous vegetables, cabbages, or mustard plants. Crops from this genus are sometimes called ''cole cr ...

'' species and varieties such as broccoli. Pentanenitrile is hydrolyzed to

valeric acid Valeric acid or pentanoic acid is a straight-chain alkyl carboxylic acid with the chemical formula . Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. It is found in the perennial flowering plant ''Valeriana officina ...

by the fungi ''

Gibberella intermedia ''Gibberella'' is a genus of fungi in the family Nectriaceae. In 1926, Japanese scientists observed that rice plants infected with ''Gibberella'' had abnormally long stems (" foolish seedling disease"). A substance, gibberellin, was derived f ...

'', ''

Fusarium oxysporum ''Fusarium oxysporum'' (Schlecht as emended by Snyder and Hansen), an ascomycete fungus, comprises all the species, varieties and forms recognized by Wollenweber and Reinking within an infrageneric grouping called section Elegans. It is part of ...

'', and ''

Aspergillus niger ''Aspergillus niger'' is a mold classified within the ''Nigri'' section of the ''Aspergillus'' genus. The ''Aspergillus'' genus consists of common molds found throughout the environment within soil and water, on vegetation, in fecal matter, on de ...

'' in which it induces production of the

nitrilase Nitrilase enzymes (nitrile aminohydrolase; ) catalyse the hydrolysis of nitriles to carboxylic acids and ammonia, without the formation of "free" amide intermediates. Nitrilases are involved in natural product biosynthesis and post translational mo ...

enzyme.

References

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