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Acetonitrile

Acetonitrile
Skeletal formula of acetonitrile
Skeletal formula of acetonitrile with all explicit hydrogens added
Ball and stick model of acetonitrile
Spacefill model of acetonitrile
Names
Preferred IUPAC name
Acetonitrile
Systematic IUPAC name
Ethanenitrile
Other names
  • Cyanomethane
  • Ethyl nitrile
  • Methanecarbonitrile
  • Methyl cyanide
Identifiers
75-05-8 YesY
3D model (Jmol) Interactive image
741857
ChEBI CHEBI:38472 YesY
ChEMBL ChEMBL45211 YesY
ChemSpider 6102 YesY
ECHA InfoCard 100.000.760
EC Number 200-835-2
895
MeSH acetonitrile
PubChem 6342
RTECS number AL7700000
UNII Z072SB282N YesY
UN number 1648
Properties
C2H3N
Molar mass 41.05 g·mol−1
Appearance Colorless liquid
Density 0.786 g/cm3
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)
530 μmol/(Pa·kg)
Acidity (pKa) 25
Basicity (pKb) −11
UV-vismax) 195 nm
Absorbance ≤0.10
−28.0×10−6 cm3/mol
1.344
Thermochemistry
91.69 J/(K·mol)
149.62 J/(K·mol)
40.16–40.96 kJ/mol
−1256.03 – −1256.63 kJ/mol
Hazards
Safety data sheet See: data page
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H225, H302, H312, H319, H332
P210, P280, P305+351+338
Highly Flammable F Harmful Xn
R-phrases R11, R20/21/22, R36
S-phrases (S1/2), S16, S36/37
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored 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)
  • 2 g/kg (dermal, rabbit)
  • 2.46 g/kg (oral, rat)
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)
16,000 ppm (dog, 4 hr)
US health exposure limits (NIOSH):
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
Related compounds
DBNPA
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Acetonitrile is the chemical compound with the formula CH
3
CN
. 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.

In the laboratory, it is used as a medium-polarity solvent that is miscible with water and a range of organic solvents, but not saturated hydrocarbons. It has a convenient liquid range and a high dielectric constant of 38.8. With a dipole moment of 3.92 D, acetonitrile dissolves a wide range of ionic and nonpolar compounds and is useful as a mobile phase in HPLC and LC–MS. The N≡C−C skeleton is linear with a short C≡N distance of 1.16 Å.

Acetonitrile was first prepared in 1847 by the French chemist Jean-Baptiste Dumas.

Acetonitrile is used mainly as a solvent in the purification of butadiene in refineries. Specifically, acetonitrile is fed into the top of a distillation column filled with hydrocarbons including butadiene, and as the acetonitrile falls down through the column, it absorbs the butadiene which is then sent from the bottom of the tower to a second separating tower. Heat is then employed in the separating tower to separate the butadiene.


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Wikipedia

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