3-chlorobenzene-1-carboperoxoic acid

• ChemBase ID: 107972
• Molecular Formular: C7H5ClO3
• Molecular Mass: 172.5658
• Monoisotopic Mass: 171.9927217
• SMILES: OOC(=O)c1cccc(Cl)c1
• Canonical SMILES: OOC(=O)c1cccc(c1)Cl
• InChI: InChI=1S/C7H5ClO3/c8-6-3-1-2-5(4-6)7(9)11-10/h1-4,10H
• InChIKey: NHQDETIJWKXCTC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-chlorobenzene-1-carboperoxoic acid
• IUPAC Traditional name: mcpba
• Synonyms: 3-Chlorobenzenecarboperoxoic Acid; NSC 97094; m-Chlorobenzoyl Hydroperoxide; m-Chloroperbenzoic Acid; m-Chloroperoxobenzoic Acid; 3-Chloroperbenzoic Acid (Technical Grade, 70-75%, wet with water); 3-Chloroperoxybenzoic acid; 3-Chloroperoxybenzoic acid; 3-Chloroperbenzoic acid; m-Chloroperoxybenzoic acid; m-CHLOROPERBENZOIC ACID; meta-Chloroperoxybenzoic acid; m-Chloroperoxybenzoic acid; meta-Chloroperbenzoic acid; 3-Chloroperbenzoic acid; mCPBA; Meta-Chloroperoxybenzoic acid; 3-Chloroperoxybenzoic acid; 3-Chlorobenzoperoxoic acid; 3-氯过氧苯甲酸; 间氯过氧苯甲酸; 3-氯过氧化苯甲酸

Database IDs

• CAS Number: 937-14-4
• EC Number: 213-322-3
• MDL Number: MFCD00002127
• Beilstein Number: 608317
• PubChem SID: 24856527; 162089126; 24855622
• PubChem CID: 70297
• Chemspider ID: 63480
• Wikipedia Title: Meta-Chloroperoxybenzoic_acid

CALCULATED PROPERTIES

• Acid pKa: 7.4827013
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.3494327
• LogD (pH = 7.4): 2.093771
• Log P: 2.3539097
• Molar Refractivity: 39.756 cm^3
• Polarizability: 15.491928 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Wet White Solid; White powder
• Melting Point: 63-67°C (dec.); 64-66°C; 69-71 °C(lit.); 92-94 °C, decomposes; 93°C
• pKa: 7.57

Safety Information

• Storage Condition: Refrigerator
• RTECS: SD9470000
• European Hazard Symbols: Oxidising (O); Irritant (Xi)
• UN Number: 3106; UN3106
• German water hazard class: 3
• Hazard Class: 5.2
• Packing Group: II
• Risk Statements: 5-8-36/37/38; 5-8-36/37/38-43; R:9-18; R7 R22 R34
• Safety Statements: 17-26-37; 26-36/37; S:13-16-27; S17 S26 S36/37/39 S45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS03; GHS07
• GHS Signal Word: Danger
• Main Hazard: Oxidizing, corrosive
• GHS Hazard statements: H242-H272-H315-H319-H335; H242-H315-H317-H319-H335
• GHS Precautionary statements: P220-P261-P280-P305 + P351 + P338-P410-P411 + P235; P220-P261-P280-P305 + P351 + P338-P410-P412; P221-P210-P305+P351+P338-P405-P410-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3106 5.2
• Storage Temperature: 2-8°C

Product Information

• Purity: ~70% (RT); ≤77%; 50-55%, cont. ca 10% 3-chlorobenzoic acid, balance water; 85%; 95+%
• Grade: technical
• Impurities: ~10% 3-chlorobenzoic acid; ~20% water
• Linear Formula: ClC6H4CO3H

DETAILS

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

Sigma Aldrich - 25800

Other Notes
Reagent for the epoxidation of olefins1

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).