Butyronitrile

Butyronitrile^[1]
Names
	Preferred IUPAC name Butanenitrile
	Other names 1-Cyanopropane; Propyl cyanide; n-Butyronitrile;
Identifiers
CAS Number	109-74-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1361452
ChEBI	CHEBI:51937 ;
ChemSpider	7717 ;
ECHA InfoCard	100.003.365
EC Number	203-700-6;
MeSH	N-butyronitrile
PubChem CID	8008;
RTECS number	ET8750000;
UNII	O3V36V0W0M ;
UN number	2411
CompTox Dashboard (EPA)	DTXSID1026823 ;
	InChI InChI=1S/C4H7N/c1-2-3-4-5/h2-3H2,1H3 Key: KVNRLNFWIYMESJ-UHFFFAOYSA-N ;
	SMILES CCCC#N;
Properties
Chemical formula	C4H7N
Molar mass	69.107 g·mol−1
Appearance	Colorless
Odor	Sharp and suffocating
Density	794 mg mL−1
Melting point	−111.90 °C; −169.42 °F; 161.25 K
Boiling point	117.6 °C; 243.6 °F; 390.7 K
Solubility in water	0.033 g/100 mL
Solubility	soluble in benzene ; miscible in alcohol, ether, dimethylformamide
Vapor pressure	3.1 kPa
Henry's law; constant (kH)	190 μmol Pa−1 kg−1
Magnetic susceptibility (χ)	-49.4·10−6 cm3/mol
Refractive index (nD)	1.38385
Dipole moment	3.5
Thermochemistry
Heat capacity (C)	134.2 J K−1 mol−1
Std enthalpy of; formation (ΔfH⦵298)	−6.8–−4.8 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−2.579 MJ mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H301, H311, H331
Precautionary statements	P210, P261, P280, P301+P310, P311
NFPA 704 (fire diamond)	3 3 0
Flash point	18 °C (64 °F; 291 K)
Autoignition; temperature	488 °C (910 °F; 761 K)
Explosive limits	1.65%–?
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	50 mg kg−1 (oral, rat)
	NIOSH (US health exposure limits):
PEL (Permissible)	none
REL (Recommended)	TWA 8 ppm (22 mg/m3)
IDLH (Immediate danger)	N.D.
Related compounds
Related alkanenitriles	Isobutyronitrile; Propanenitrile; Malononitrile; Pivalonitrile; Succinonitrile; Glutaronitrile;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Butyronitrile or butanenitrile or propyl cyanide, is a nitrile with the formula C₃H₇CN. This colorless liquid is miscible with most polar organic solvents.

Uses

Butyronitrile is mainly used as a precursor to the poultry drug amprolium.^[4]

It also has recognized use in the synthesis of Etifelmine.

Synthesis

Butyronitrile is prepared industrially by the ammoxidation of n-butanol:

C₃H₇CH₂OH + NH₃ + O₂ → C₃H₇CN + 3 H₂O

Occurrence in space

Butyronitrile has been detected in the Large Molecule Heimat in Sagittarius B2 cloud along with other complex organic molecules.^[5]

References

^ Merck Index, 11th Edition, 1597
^ ^a ^b ^c ^d ^e ^f ^g ^h NIOSH Pocket Guide to Chemical Hazards. "#0086". National Institute for Occupational Safety and Health (NIOSH).
^ "N-butyronitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 12 June 2012.
^ Peter Pollak, Gérard Romeder, Ferdinand Hagedorn, Heinz-Peter Gelbke "Nitriles" Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_363
^ "Two highly complex organic molecules detected in space". Royal Astronomical Society. 21 April 2009. Retrieved 29 September 2015.

External links

[1] Merck Index, 11th Edition, 1597

[PGCH-2] ^ ^a ^b ^c ^d ^e ^f ^g ^h NIOSH Pocket Guide to Chemical Hazards. "#0086". National Institute for Occupational Safety and Health (NIOSH).

[3] "N-butyronitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 12 June 2012.

[4] Peter Pollak, Gérard Romeder, Ferdinand Hagedorn, Heinz-Peter Gelbke "Nitriles" Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_363

[ras-5] "Two highly complex organic molecules detected in space". Royal Astronomical Society. 21 April 2009. Retrieved 29 September 2015.

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