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| Names | |||
|---|---|---|---|
| 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 |
| ||
| 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: | |||
 
| |||
| 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)
|
50 mg kg−1 (oral, rat) | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible)
|
none[2] | ||
REL (Recommended)
|
TWA 8 ppm (22 mg/m3)[2] | ||
IDLH (Immediate danger)
|
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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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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Nitration of aromatics using nitric acid
Transcription
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
This page was last edited on 28 July 2023, at 04:36