Butyronitrile

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

Butyronitrile^[1]

Names
Preferred IUPAC name Butanenitrile[2]
Other names 1-Cyanopropane[3] Propyl cyanide[3] n-Butyronitrile[3]
Identifiers
CAS Number	109-74-0 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1361452
ChEBI	CHEBI:51937 N
ChemSpider	7717 N
ECHA InfoCard	100.003.365
EC Number	203-700-6
MeSH	N-butyronitrile
PubChem CID	8008
RTECS number	ET8750000
UNII	O3V36V0W0M Y
UN number	2411
CompTox Dashboard (EPA)	DTXSID1026823
InChI InChI=1S/C4H7N/c1-2-3-4-5/h2-3H2,1H3 N Key: KVNRLNFWIYMESJ-UHFFFAOYSA-N N
SMILES CCCC#N
Properties
Chemical formula	C4H7N
Molar mass	69.107 g·mol−1
Appearance	Colorless
Odor	Sharp and suffocating[3]
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%–?[3]
Lethal dose or concentration (LD, LC):
LD50 (median dose)	50 mg kg−1 (oral, rat)
NIOSH (US health exposure limits):
PEL (Permissible)	none[3]
REL (Recommended)	TWA 8 ppm (22 mg/m3)[3]
IDLH (Immediate danger)	N.D.[3]
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). N verify (what is YN ?) Infobox references

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]