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273031

Sigma-Aldrich

3-Chloroperbenzoic acid

≤77%

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Synonym(s):
meta-Chloroperbenzoic acid, 3-Chloroperoxybenzoic acid, MCPBA
Linear Formula:
ClC6H4CO3H
CAS Number:
937-14-4
Molecular Weight:
172.57
Beilstein:
608317
MDL number:
MFCD00002127
UNSPSC Code:
12352302
PubChem Substance ID:
24856527
NACRES:
NA.22

Quality Level

200

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

Signal Word

Danger

Hazard Statements

H242,H314,H317,H410

Hazard Classifications

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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
Rearrangements of organic peroxides and related processes.
Yaremenko I
Beilstein Journal of Organic Chemistry, 12, 1647-1647 (2016)
Reactive mono-and di-epoxy-functionalized poly (3-hydroxybutyrate) s. Synthesis and characterization.
Michalak M
Polymer Degradation and Stability, 97(10), 1861-1870 (2012)
Shin Kamijo et al.
Organic letters, 12(18), 4195-4197 (2010-08-26)
The direct oxidation of ether sp(3) C-H bonds using the new reagent system mCPBA/CCl(3)CN/MeCN has been developed. CCl(3)CN in MeCN drastically alters the reactivity of m-chloroperbenzoic acid (mCPBA), and chemoselective transformation of methyl ethers to ketones was realized under mild
Marie Af Delgove et al.
Journal of chemical technology and biotechnology (Oxford, Oxfordshire : 1986), 93(8), 2131-2140 (2018-08-03)
It is widely accepted that the poor thermostability of Baeyer-Villiger monooxygenases limits their use as biocatalysts for applied biocatalysis in industrial applications. The goal of this study was to investigate the biocatalytic oxidation of 3,3,5-trimethylcyclohexanone using a thermostable cyclohexanone monooxygenase
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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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