Acetonitrile

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Acetonitrile
Image:Acetonitrile-skeletal.png
Image:Acetonitrile-3D-vdW.png
IUPAC name	Ethanenitrile
Other names	Methyl cyanide
Identifiers
CAS number	75-05-8
RTECS number	AL7700000
SMILES	CC#N
InChI	InChI=1/C2H3N/c1-2-3/h1H3
Properties
Molecular formula	CH3CN
Molar mass	41.05 g/mol
Appearance	colorless liquid
Density	0.786 g/mL liquid
Melting point	-45 °C
Boiling point	82 °C
Solubility in water	miscible
Solubility	organic solvents
Acidity (pKa)	25
Hazards
EU classification	Flammable, harmful
NFPA 704	3 2 0
R-phrases	R11, R20/21/22, R36
S-phrases	(S1/2), S16, S36/37
Flash point	2 °C
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 CH₃CN. This colourless liquid is the simplest organic nitrile and is widely used as a solvent.

Contents 1 Industrial applications 2 Laboratory uses 3 Safety 4 External links 5 References

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: INEOS, 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 compounds without complications due to the fact that it contains no acidic protons. Acetone has similar properties but is more acidic and more reactive toward bases and nucleophiles. (Note: the pK_a given applies to the conjugate acid of acetonitrile, not the molecule itself.)

In inorganic chemistry, acetonitrile is widely employed as a displaceable ligand where it is abbreviated MeCN. A good example is the use of PdCl₂(MeCN)₂ prepared by refluxing polymeric palladium chloride in acetonitrile.

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]}

External links

• WebBook page for C₂H₃N
• International Chemical Safety Card 0088
• National Pollutant Inventory - Acetonitrile fact sheet
• NIOSH Pocket Guide to Chemical Hazards

References

1. ↑ DiBiase, S. A.; Beadle, J. R.; Gokel, G. W.. "Synthesis of α,β-Unsaturated Nitriles from Acetonitrile: Cyclohexylideneacetonitrile and Cinnamonitrile". Org. Synth.; Coll. Vol. 7: 108. 

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