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Sigma-Aldrich

3-Chloroperbenzoic acid

≤77%

Synonym(s):

meta-Chloroperbenzoic acid, 3-Chloroperoxybenzoic acid, MCPBA

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About This Item

Linear Formula:
ClC6H4CO3H
CAS Number:
937-14-4
Molecular Weight:
172.57
Beilstein/REAXYS Number:
608317
MDL number:
MFCD00002127
UNSPSC Code:
12352302
PubChem Substance ID:
24856527
NACRES:
NA.22

assay

≤77%

form

solid

reaction suitability

reagent type: oxidant

mp

69-71 °C (lit.)

storage temp.

2-8°C

SMILES string

OOC(=O)c1cccc(Cl)c1

InChI

1S/C7H5ClO3/c8-6-3-1-2-5(4-6)7(9)11-10/h1-4,10H

InChI key

NHQDETIJWKXCTC-UHFFFAOYSA-N

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General description

3-Chloroperbenzoic acid is a strong oxidizing agent mainly used for the epoxidation of alkenes and also in the Baeyer-Villiger oxidation of ketones to esters.

Application

3-Chloroperbenzoic acid has been used in the oxidation of N-p-tolylsulfinyl-(E)-1-phenylethylideneimine to N-p-tolylsulfonyl (E)-1-phenylethylideneimine using dichloromethane as a solvent. It has also been used in the preparation of mono- and di-epoxy-functionalized poly(3-hydroxybutyrate)-based reactive polymers. MCPBA is also an effective oxidizing agent for conversion of α-amide substituted polyesters to their corresponding polysulfones with tunable thermal properties.
Effective oxidant for epoxidizing di-, tri-, and tetra-substituted olefins.

Other Notes

remainder 3-chlorobenzoic acid and water

signalword

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Org. Perox. D - Skin Corr. 1C - Skin Sens. 1

Storage Class

5.2 - Organic peroxides and self-reacting hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Lorenzo Gualandi et al.
Physical chemistry chemical physics : PCCP, 21(7), 3558-3563 (2018-09-20)
The synthesis of novel dibenzo-24-crown ether substituted nitroxides and their use as spin probes for the detection of cation guests by EPR are reported. Formation of a host-guest complex between the proposed spin probes and several cations, both organic and
Reactive mono-and di-epoxy-functionalized poly (3-hydroxybutyrate) s. Synthesis and characterization.
Michalak M
Polymer Degradation and Stability, 97(10), 1861-1870 (2012)
Preparation of N?p?Tolylsulfonyl?(E)?1?Phenylethylideneimine.
Ruano J
Organic Syntheses, 129-138 (2007)
Rearrangements of organic peroxides and related processes.
Yaremenko I
Beilstein Journal of Organic Chemistry, 12, 1647-1647 (2016)
Passerini addition polymerization of an AB-type monomer?a convenient route to versatile polyesters.
Sehlinger A
European Polymer Journal, 50, 150-157 (2014)
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Articles

Baeyer-Villiger Oxidation Reaction

The Baeyer-Villiger oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts the ketones to esters and the cyclic ketones to lactones.

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