Acetonitrile
Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula CH3CN and structure H3C−C≡N. This colourless liquid is the simplest organic nitrile (hydrogen cyanide is a simpler nitrile, but the cyanide anion is not classed as organic). It is produced mainly as a byproduct of acrylonitrile manufacture. It is used as a polar aprotic solvent in organic synthesis and in the purification of butadiene. The N≡C−C skeleton is linear with a short C≡N distance of 1.16 Å.
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| Names | |||
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| Preferred IUPAC name
Acetonitrile | |||
| Systematic IUPAC name
Ethanenitrile | |||
Other names
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| Identifiers | |||
3D model (JSmol) |
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| 741857 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.000.760 | ||
| EC Number |
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| 895 | |||
| MeSH | acetonitrile | ||
PubChem CID |
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| RTECS number |
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| UNII | |||
| UN number | 1648 | ||
CompTox Dashboard (EPA) |
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SMILES
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| Properties | |||
| C2H3N | |||
| Molar mass | 41.053 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Odor | Faint, distinct, fruity | ||
| Density | 0.786 g/cm3 at 25°C | ||
| Melting point | −46 to −44 °C; −51 to −47 °F; 227 to 229 K | ||
| Boiling point | 81.3 to 82.1 °C; 178.2 to 179.7 °F; 354.4 to 355.2 K | ||
| Miscible | |||
| log P | −0.334 | ||
| Vapor pressure | 9.71 kPa (at 20.0 °C) | ||
Henry's law constant (kH) |
530 μmol/(Pa·kg) | ||
| Acidity (pKa) | 25 | ||
| UV-vis (λmax) | 195 nm | ||
| Absorbance | ≤0.10 | ||
Magnetic susceptibility (χ) |
−28.0×10−6 cm3/mol | ||
Refractive index (nD) |
1.344 | ||
| 3.92 D | |||
| Thermochemistry | |||
Heat capacity (C) |
91.69 J/(K·mol) | ||
Std molar entropy (S⦵298) |
149.62 J/(K·mol) | ||
Std enthalpy of formation (ΔfH⦵298) |
40.16–40.96 kJ/mol | ||
Std enthalpy of combustion (ΔcH⦵298) |
−1256.03 – −1256.63 kJ/mol | ||
| Hazards | |||
| GHS labelling: | |||
| Danger | |||
| H225, H302, H312, H319, H332 | |||
| P210, P280, P305+P351+P338 | |||
| NFPA 704 (fire diamond) |
2
3
0 | ||
| Flash point | 2.0 °C (35.6 °F; 275.1 K) | ||
| 523.0 °C (973.4 °F; 796.1 K) | |||
| Explosive limits | 4.4–16.0% | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) |
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LC50 (median concentration) |
5655 ppm (guinea pig, 4 hr) 2828 ppm (rabbit, 4 hr) 53,000 ppm (rat, 30 min) 7500 ppm (rat, 8 hr) 2693 ppm (mouse, 1 hr) | ||
LCLo (lowest published) |
16,000 ppm (dog, 4 hr) | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) |
TWA 40 ppm (70 mg/m3) | ||
REL (Recommended) |
TWA 20 ppm (34 mg/m3) | ||
IDLH (Immediate danger) |
500 ppm | ||
| Related compounds | |||
Related alkanenitriles |
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Related compounds |
DBNPA | ||
| Supplementary data page | |||
| Acetonitrile (data page) | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |||
Acetonitrile was first prepared in 1847 by the French chemist Jean-Baptiste Dumas.
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