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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| Names | |||
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| Preferred IUPAC name
Butanenitrile[3] | |||
| Other names | |||
| Identifiers | |||
3D model (JSmol)
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| 1361452 | |||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.003.365 | ||
| EC Number |
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| MeSH | N-butyronitrile | ||
PubChem CID
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| RTECS number |
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| UNII | |||
| UN number | 2411 | ||
CompTox Dashboard (EPA)
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| Properties | |||
| C4H7N | |||
| Molar mass | 69.107 g·mol−1 | ||
| Appearance | Colorless | ||
| Odor | Sharp and suffocating[2] | ||
| 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 | ||
| 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 | ||
| -49.4·10−6 cm3/mol | |||
Refractive index (nD)
|
1.38385 | ||
| 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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| Danger | |||
| H225, H301, H311, H331 | |||
| P210, P261, P280, P301+P310, P311 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 18 °C (64 °F; 291 K) | ||
| 488 °C (910 °F; 761 K) | |||
| Explosive limits | 1.65%–?[2] | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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50 mg kg−1 (oral, rat) | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible)
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none[2] | ||
REL (Recommended)
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TWA 8 ppm (22 mg/m3)[2] | ||
IDLH (Immediate danger)
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N.D.[2] | ||
| Related compounds | |||
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).
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Uses
editButyronitrile is mainly used as a precursor to the poultry drug amprolium.[4]
It also has recognized use in the synthesis of Etifelmine.
Synthesis
editButyronitrile is prepared industrially by the ammoxidation of n-butanol:
- C3H7CH2OH + NH3 + O2 → C3H7CN + 3 H2O
Occurrence in space
editButyronitrile has been detected in the Large Molecule Heimat in Sagittarius B2 cloud along with other complex organic molecules.[5]
References
edit- ^ 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.