Acetonitrile
Organic compound (CH3−C≡N); Simplest organic nitrile / From Wikipedia, the free encyclopedia
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Not to be confused with Acetyl cyanide.
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.[5] The N≡C−C skeleton is linear with a short C≡N distance of 1.16 Å.[6]
Quick Facts Names, Identifiers ...
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Names | |||
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Preferred IUPAC name
Acetonitrile[1] | |||
Systematic IUPAC name
Ethanenitrile[1] | |||
Other names | |||
Identifiers | |||
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3D model (JSmol) |
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741857 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider |
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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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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 | ||
−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: | |||
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Danger | |||
H225, H302, H312, H319, H332 | |||
P210, P280, P305+P351+P338 | |||
NFPA 704 (fire diamond) | |||
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)[3] | ||
LCLo (lowest published) |
16,000 ppm (dog, 4 hr)[3] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible) |
TWA 40 ppm (70 mg/m3)[4] | ||
REL (Recommended) |
TWA 20 ppm (34 mg/m3)[4] | ||
IDLH (Immediate danger) |
500 ppm[4] | ||
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).
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Close
Acetonitrile was first prepared in 1847 by the French chemist Jean-Baptiste Dumas.[7]