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Meta-Chloroperoxybenzoic acid



Template:DISPLAYTITLE:meta-Chloroperoxybenzoic acid

Meta-Chloroperoxybenzoic acid
IUPAC name 3-chloroperoxybenzoic acid
Other names meta-chloroperoxybenzoic acid;

Additional recommended knowledge

m-chloroperoxybenzoic acid; meta-chloroperbenzoic acid; 3-chloroperbenzoic acid; mCPBA

Identifiers
CAS number 937-14-4
RTECS number SD9470000
SMILES O=C(OO)C1=CC(Cl)=CC=C1
Properties
Molecular formula C7H5ClO3
Molar mass 172.57 g/mol
Appearance White powder
Melting point

92 - 94 °C, decomposes

Acidity (pKa) 7.57
Hazards
Main hazards Oxidizing, corrosive
R-phrases R7 R22 R34
S-phrases S17 S26 S36/37/39 S45
Related Compounds
Related compounds peroxyacetic acid; peroxybenzoic acid
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

meta-Chloroperoxybenzoic acid (mCPBA) is a peroxy acid with chemical formula C7H5ClO3.

mCPBA is a strong oxidizing agent that may cause fire upon contact with flammable material. It is an example of a peroxycarboxylic acid. As a pure substance, it can be detonated by shock or by sparks. It is therefore sold commercially as a much more stable mixture that is about 75% mCPBA with the balance being 3-chlorobenzoic acid and water.

mCPBA is used widely as a reagent in organic chemistry to carry out a variety of chemical transformations. It is often preferred to other peroxy acids because of its relative ease of handling. The main areas of use are the conversion of ketones to esters (Baeyer-Villiger oxidation), epoxidation of alkenes, oxidation of sulfides to sulfoxides and sulfones, and oxidation of amines to produce amine oxides.

Epoxidation example

The following reaction shows how mCPBA transforms an alkene into an epoxide. The mechanism is shown as follows:

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Meta-Chloroperoxybenzoic_acid". A list of authors is available in Wikipedia.
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