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| Names | |||
|---|---|---|---|
| Preferred IUPAC name Propanenitrile[5] | |||
| Other names | |||
| Identifiers | |||
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3D model (JSmol) | |||
| 773680 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
| ||
| ECHA InfoCard | 100.003.151 | ||
| EC Number |
| ||
| MeSH | propionitrile | ||
| RTECS number |
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| UNII | |||
| UN number | 2404 | ||
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| Properties | |||
| C3H5N | |||
| Molar mass | 55.080 g·mol−1 | ||
| Appearance | Colourless liquid | ||
| Odor | Sweetish, pleasant, ethereal[6] | ||
| Density | 772 mg mL−1 | ||
| Melting point | −100 to −86 °C; −148 to −123 °F; 173 to 187 K | ||
| Boiling point | 96 to 98 °C; 205 to 208 °F; 369 to 371 K | ||
| 11.9% (20 °C)[6] | |||
| logP | 0.176 | ||
| Vapor pressure | 270 μmol Pa−1 kg−1 | ||
| −38.5·10−6 cm3/mol | |||
Refractive index (nD) | 1.366 | ||
| Thermochemistry | |||
| 105.3 J K−1 mol−1 | |||
Std molar entropy(S⦵298) | 189.33 J K−1 mol−1 | ||
Std enthalpy of formation(ΔfH⦵298) | 15.5 kJ mol−1 | ||
Std enthalpy of combustion(ΔcH⦵298) | −1.94884–−1.94776 MJ mol−1 | ||
| Hazards | |||
| GHS labelling: | |||
  | |||
| Danger | |||
| H225,H300,H310,H319,H332 | |||
| P210,P264,P280,P301+P310,P302+P350,P305+P351+P338 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 6 °C (43 °F; 279 K) | ||
| Explosive limits | 3.1%-?[6] | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) | 39 mg kg−1(oral, rat) | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) | none[6] | ||
REL (Recommended) | TWA 6 ppm (14 mg/m3)[6] | ||
IDLH (Immediate danger) | N.D.[6] | ||
| Related compounds | |||
Related alkanenitriles | |||
Related compounds | DBNPA | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Propionitrile, also known asethyl cyanide andpropanenitrile, is anorganic compound with the formula CH3CH2CN. It is a simple aliphaticnitrile. The compound is a colourless, water-soluble liquid. It is used as a solvent and a precursor to other organic compounds.[7]
The main industrial route to this nitrile is the hydrogenation ofacrylonitrile. It is also prepared by theammoxidation ofpropanol (propionaldehyde can also be used instead):[7]
Propionitrile is a byproduct of the electrodimerisation of acrylonitrile toadiponitrile.
In the laboratory propanenitrile can also be produced by thedehydration ofpropionamide, by catalytic reduction ofacrylonitrile, or by distillingethyl sulfate andpotassium cyanide.
Propionitrile is a solvent similar toacetonitrile but with a slightly higher boiling point. It is a precursor to propylamines by hydrogenation. It is a C-3 building block in the preparation of the drugflopropione by theHouben-Hoesch reaction.
The nitrile aldol reaction withbenzophenone, followed by reduction of the nitrile with lithium aluminium hydride gives2-MDP. This agent possessesappetite suppressant and antidepressant properties.
The toxicityLD50 of propionitrile is listed as 39 mg/kg[8] and as 230 my (both rats, oral).[7]
In 1979, the Kalama (Vega) plant inBeaufort,South Carolina experienced an explosion during the production of propionitrile by nickel-catalyzed hydrogenation of acrylonitrile.[9] This site is now one of the twoSuperfund cleanup sites in South Carolina.[9]
