My watch list
my.chemeurope.com  
Login  

Acetonitrile



Acetonitrile
IUPAC name Ethanenitrile
Other names Methyl cyanide; cyanomethane
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
MSDS External MSDS
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
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
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.

Additional recommended knowledge

Contents

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 United States of America.[citation needed]

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.

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]

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. 
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Acetonitrile". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE