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Acetonitrile

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Acetonitrile
Acetonitrile skeletal structure

Acetonitrile Acetonitrile space-filling model

General
Other names Ethanenitrile
Methyl cyanide
Molecular formula CH3CN
SMILES CC#N
Molar mass 41.05 g/mol
Appearance colorless liquid
CAS number [75-05-8]
Properties
Density and phase 0.786 g/ml, liquid
Solubility in water Miscible
Melting point −48 °C
Boiling point 82 °C
Acidity (pKa) -10
Basicity (pKb) ?
Viscosity 0.345 cP at 25 °C
Thermodynamic data
Standard enthalpy
of formation ΔfHoliquid 		? kJ/mol
Standard enthalpy
of combustion ΔcHoliquid 		? kJ/mol
Standard molar entropy
Soliquid 		? J.K−1.mol−1
Hazards
EU classification Flammable (F)
Harmful (Xn)
R-phrases Template:R11, Template:R20/21/22, Template:R36
S-phrases Template:S1/2, Template:S16, Template:S36/37
NFPA 704
NFPA 704
safety square
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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. gasolineInstability (yellow): no hazard codeSpecial hazards (white): no code
2
3
Flash Point 2 C
Supplementary data page
Structure and
properties 		n, εr, etc.
Thermodynamic
data 		Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Regulatory data Flash point,
RTECS number, etc.
Related compounds
Related nitriles Propionitrile
Butyronitrile
Related compounds Acetic acid
Acetamide
Ethylamine
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references

Acetonitrile is the chemical compound with formula of CH3CN. This colourless liquid is the simplest organic nitrile and is widely used as a solvent.

Industrial applications

Acetonitrile is used as a solvent but also as an intermediate in the production of many chemicals ranging from pesticides to perfumes. Production trends for acetonitrile generally follow those of acrylonitrile. The four main producers of acetonitrile in the United States are: BP Chemicals, DuPont, J.T. Baker Chemical, and Sterling Chemicals. In 1992, 32.3 million pounds (14,700 t) of acetonitrile were produced in the U.S.

Laboratory uses

Acetonitrile is commonly the solvent of choice for testing an unknown chemical reaction. It is polar with a convenient liquid range. It dissolves a wide range of chemical compounds without complications due to the presence of acidic protons. Acetone has similar properties but is more acidic and more reactive toward bases and nucleophiles. (Note: the pKa given applies to the conjugate acid of acetonitrile, not the molecule itself.)

In inorganic chemistry, acetonitrile is widely employed as a dispaceable ligand where it is abbreviated MeCN. A good example is the use of PdCl2(MeCN)2 prepared by refluxing polymeric palladium chloride in acetonitrile to obtain a solution of more reactive molecular palladium species.

It is a popular solvent in cyclic voltammetry because of its relatively high dielectric constant. MeCN is a two-carbon building block in organic synthesis.[1] Acetonitrile is also commonly used in column chromatography and the more modern high performance liquid chromatography where it serves as a mobile phase in the separation of molecules.

Safety

Acetonitrile is toxic and flammable. It is metabolized into hydrogen cyanide and thiocyanate.[citation needed]

Template:ChemicalSources

References

  1. ^ DiBiase, S. A.; Beadle, J. R.; Gokel, G. W. “Synthesis of α,β-Unsaturated Nitriles from Acetonitrile: Cyclohexylideneacetonitrile and Cinnamonitrile” Organic Syntheses, Collective Volume 7, page 108.
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