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273031

Sigma-Aldrich

3-Chloroperbenzoic acid

≤77%

Synonym(s):
meta-Chloroperbenzoic acid, 3-Chloroperoxybenzoic acid, MCPBA
Linear Formula:
ClC6H4CO3H
CAS Number:
Molecular Weight:
172.57
Beilstein:
608317
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≤77%

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

Effective oxidant for epoxidizing di-, tri-, and tetra-substituted olefins.
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.

Packaging

25, 100, 500 g in poly bottle
1 kg in poly bottle
10 kg in poly drum

Other Notes

remainder 3-chlorobenzoic acid and water

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Classifications

Eye Irrit. 2 - Org. Perox. D - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Chiral Mn (III) salen complexes covalently bonded on modified MCM-41 and SBA-15 as efficient catalysts for enantioselective epoxidation of nonfunctionalized alkenes.
Kureshy R
J. Catal., 238(1), 134-141 (2006)
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)
Preparation of N?p?Tolylsulfonyl?(E)?1?Phenylethylideneimine.
Ruano J
Organic Syntheses, 129-138 (2007)
Evgeny V Kudrik et al.
Nature chemistry, 4(12), 1024-1029 (2012-11-24)
High-valent oxo-metal complexes are involved in key biochemical processes of selective oxidation and removal of xenobiotics. The catalytic properties of cytochrome P-450 and soluble methane monooxygenase enzymes are associated with oxo species on mononuclear iron haem and diiron non-haem platforms

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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