CAS 937-14-4|m-CHLOROPERBENZOIC ACID|3-chlorobenzene-1-carboperoxoic acid|m-Chloroperoxybenzoic acid|3-Chloroperbenzoic acid|Meta-Chloroperoxybenzoic acid|<i>meta</i>-Chloroperbenzoic acid|<i>meta</...

General Information

Structure

Molecular Formula

C₇H₅ClO₃

Molecular Mass

172.5658

Exact Mass

171.9927217

Charge

InChI

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

InChIKey

NHQDETIJWKXCTC-UHFFFAOYSA-N

Canonic Smiles

OOC(=O)c1cccc(c1)Cl

Isomeric Smiles

OOC(=O)c1cccc(Cl)c1

Calculated Properties

JChem

Acid pKa

7.4827013

H Acceptors

H Donor

LogD (pH = 5.5)

2.3494327

LogD (pH = 7.4)

2.093771

Log P

2.3539097

Molar Refractivity

39.756

Polarizability

15.491928

Polar Surface Area

46.53

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

m-CHLOROPERBENZOIC ACIDm-Chloroperoxybenzoic acid3-Chloroperbenzoic acidMeta-Chloroperoxybenzoic acidmeta-Chloroperbenzoic acidmeta-Chloroperoxybenzoic acidm-Chloroperoxybenzoic acidmCPBA3-Chloroperbenzoic acid3-氯过氧苯甲酸3-Chloroperoxybenzoic acid间氯过氧苯甲酸m-Chloroperbenzoic Acid3-Chlorobenzenecarboperoxoic Acidm-Chloroperoxobenzoic AcidNSC 97094m-Chlorobenzoyl Hydroperoxide3-Chloroperbenzoic Acid (Technical Grade, 70-75%, wet with water)3-Chloroperoxybenzoic acid3-Chlorobenzoperoxoic acid3-Chloroperoxybenzoic acid3-氯过氧化苯甲酸

IUPAC name

3-chlorobenzene-1-carboperoxoic acid

IUPAC Traditional name

mcpba

Names and Identifiers

Registration numbers

Wikipedia Title

Meta-Chloroperoxybenzoic_acid

Chemspider ID

63480

CAS Number

937-14-4

PubChem CID

70297

PubChem SID

1620891262485652724855622

EC Number

213-322-3

Beilstein Number

608317

MDL Number

MFCD00002127

Registration numbers

Properties

Related Proteins

No Data Available

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Related Proteins

Molecular Spectra

No Data Available

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Molecule Details

Wikipedia

Meta-Chloroperoxybenzoic_acid

Sigma Aldrich

273031

Application
Effective oxidant for epoxidizing di-, tri-, and tetra-substituted olefins.
Other Notes
remainder 3-chlorobenzoic acid and water
Packaging
1 kg in poly bottle
25, 100, 500 g in poly bottle

25800

Other Notes
Reagent for the epoxidation of olefins1

Molecule Details

References

PubChem Literature

From Data Sources

• Carbonyl compounds undergo the Baeyer-Villiger reaction to give esters or lactones: J. Org. Chem., 29, 2914 (1964). For an extensive review of the Baeyer-Villiger reaction, see: Org. React., 43, 251 (1993).

• WARNING: The reagent has been reported to react exothermically with DMF: Org. Process Res. Dev., 6, 159 (2004).

• Reagent for epoxidation of alkenes: J. Org. Chem., 29, 1976 (1964). Dichloromethane has been recommended as solvent for these reactions, since the peracid is soluble, but the by-product, 3-chlorobenzoic acid, is almost insoluble. For high-yield, stereospecific epoxidation in a two-phase, almost neutral system, see: J. Org. Chem., 44, 1351 (1979). For regioselective epoxidation of the more substituted double bond of a diene, see: Org. Synth. Coll., 5, 467 (1973). For epoxidation in aqueous solution followed by in situ hydrolysis to the trans-diol by 10% sulfuric acid, see: Synth. Commun., 19, 1939 (1989).

• Sulfides can be oxidized selectively either to sulfoxides or sulfones: Tetrahedron, 22, 1235 (1966); J. Chem. Soc. (C), 2720 (1969); J. Org. Chem., 35, 2106 (1970).

• For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 664 (2007).

• Primary aliphatic amines are oxidized to nitro-compounds: J. Org. Chem., 31, 524 (1966). Good yields are obtained in 1,2-dichloroethane solution: J. Org. Chem., 44, 659 (1979); 54, 2869 (1989).

• For the stereospecific oxidation of imines to oxaziridines under phase-transfer conditions, see: Org. Synth. Coll., 8, 546 (1993):

• Perfluorooxaziridines have been prepared using acetonitrile as solvent: J. Org. Chem., 58, 4754 (1993).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

3-chlorobenzene-1-carboperoxoic acid

IUPAC Traditional name

mcpba

Molecule Details

Wikipedia

Meta-Chloroperoxybenzoic_acid

Sigma Aldrich

273031

25800

Other Notes
Reagent for the epoxidation of olefins1

References

PubChem Literature

From Data Sources

• WARNING: The reagent has been reported to react exothermically with DMF: Org. Process Res. Dev., 6, 159 (2004).

• Sulfides can be oxidized selectively either to sulfoxides or sulfones: Tetrahedron, 22, 1235 (1966); J. Chem. Soc. (C), 2720 (1969); J. Org. Chem., 35, 2106 (1970).

• For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 664 (2007).

• For the stereospecific oxidation of imines to oxaziridines under phase-transfer conditions, see: Org. Synth. Coll., 8, 546 (1993):

• Perfluorooxaziridines have been prepared using acetonitrile as solvent: J. Org. Chem., 58, 4754 (1993).

Bioactivity

PubChem BioAssay