Butyronitrile or butanenitrile or propyl cyanide, is a nitrile with the formula C3H7CN. This colorless liquid is miscible with most polar organic solvents.
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| Preferred IUPAC name Butanenitrile | |||
Other names
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| Identifiers | |||
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3D model (JSmol) |
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Beilstein Reference | 1361452 | ||
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| ECHA InfoCard | 100.003.365 | ||
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| MeSH | N-butyronitrile | ||
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| UNII |
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| UN number | 2411 | ||
CompTox Dashboard (EPA) |
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| 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: | |||
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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. | ||
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Related alkanenitriles |
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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 | |||
Uses
Butyronitrile is mainly used as a precursor to the poultry drug amprolium.
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.
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