3-Chloroperoxybenzoic acid

• Catalog No.: L00286
• CAS Number: 937-14-4
• M. F.: C7H5ClO3
• M. W.: 172.5658
• Purity: 50-55%, cont. ca 10% 3-chlorobenzoic acid, balance water

SYNONYMS

• Title: 3-氯过氧化苯甲酸
• IUPAC name: 3-chlorobenzene-1-carboperoxoic acid
• IUPAC Traditional name: mcpba
• Synonyms: m-Chloroperbenzoic Acid; mCPBA

DATABASE IDS

• CAS Number: 937-14-4
• MDL Number: MFCD00002127
• Beilstein Number: 608317
• EC Number: 213-322-3

PROPERTIES

• Purity: 50-55%, cont. ca 10% 3-chlorobenzoic acid, balance water
• Melting Point: 64-66°C
• GHS Hazard statements: H242-H272-H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• European Hazard Symbols: Oxidising (O)
• GHS Precautionary statements: P221-P210-P305+P351+P338-P405-P410-P501A
• Risk Statements: 5-8-36/37/38
• RTECS: SD9470000
• Safety Statements: 17-26-37
• TSCA Listed: 是
• Hazard Class: 5.2
• UN Number: UN3106
• Packing Group: II

REFERENCES

• 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).
• 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).
• 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).
• 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 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).
• For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 664 (2007).
• WARNING: The reagent has been reported to react exothermically with DMF: Org. Process Res. Dev., 6, 159 (2004).