Pentanenitrile

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

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

1. Buhler, D. R.; Reed, D. J. (2013). Nitrogen and Phosphorus Solvents. Elsevier. pp. 359–362. ISBN   978-1-4832-9020-1.
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 . hdl: 2027/spo.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.