3-Chloroperoxybenzoic acid

Base Information

• Chemical Name: 3-Chloroperoxybenzoic acid
• CAS No.: 937-14-4
• Molecular Formula: C7H5ClO3
• Molecular Weight: 172.568
• Hs Code.: 29163990
• European Community (EC) Number: 213-322-3
• NSC Number: 97094
• UN Number: 3106
• UNII: G203D4H1RB
• DSSTox Substance ID: DTXSID0061325
• Nikkaji Number: J27.520D
• Wikipedia: Meta-Chloroperoxybenzoic_acid
• Wikidata: Q284996
• Metabolomics Workbench ID: 58086
• ChEMBL ID: CHEMBL458855
• Mol file: 937-14-4.mol

Synonyms:3-chloroperbenzoic acid;3-chloroperoxybenzoic acid;m-chloroperbenzoic acid;m-CPBA;MCPBA;meta-chloroperoxybenzoic acid

Chemical Property of 3-Chloroperoxybenzoic acid

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 69-71 °C(lit.)
• Refractive Index: 1.571
• Boiling Point: 305.5 °C at 760 mmHg
• PKA: 7.57 (in water @ 25 °C)
• Flash Point: 138.6 °C
• PSA: 46.53000
• Density: 1.435 g/cm³
• LogP: 1.96980
• Storage Temp.: 2-8°C
• Water Solubility.: insoluble
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 171.9927217
• Heavy Atom Count: 11
• Complexity: 149
• Transport DOT Label: Organic Peroxide

Purity/Quality:

98% ^*data from raw suppliers

3-ChloroperbenzoicAcid(TechnicalGrade,wetwithwater) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): O,Xi,C
• Hazard Codes: O,Xi,C
• Statements: 5-8-36/37/38-43-7-34-22
• Safety Statements: 17-26-36/37-45-36/37/39-3/7-14-27-7/9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: C1=CC(=CC(=C1)Cl)C(=O)OO
• Uses: 3-Chloroperoxybenzoic acid is commonly used in double bond epoxidation, nitridation, cyclization, Baeyer-Villiger oxidation, and N-oxidation. It can also be used as an oxidant for fine chemicals such as synthetic medicine and pesticides. It is also sometimes used as a bleaching agent [1-6]. ? Used in cyclization reaction, Baeyer-Villiger reaction, N-oxidation reaction and S-oxidation reaction. ? Used as an oxidant for fine chemical products such as synthetic medicine and pesticides. ? Used as oxidant and bleach. ? As a good electrophilic reagent, it can react with many functional groups and can oxidize olefins, enol silyl ethers, furans, sulfides, selenides and amino compounds. 3-Chloroperoxybenzoic acid is a strong oxidizing agent used in the oxidation reactions such as aldehydes and ketones to esters (Bayer-Villiger-Oxidation), olefines to epoxides, sulfides to sulfoxides and sulfones, and amines to nitroalkanes, N-oxides. Effective oxidant for epoxidizing di-, tri-, and tetra-substituted olefins.

Technology Process of 3-Chloroperoxybenzoic acid

There total 13 articles about 3-Chloroperoxybenzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.7%

3-chlorobenzamide (618-48-4) → 3-chloro-benzenecarboperoxoic acid (937-14-4)

Guidance literature:

3-chlorobenzamide; With sodium nitrite; N-bromoacetamide; at 16 ℃; for 2.16667h;

With zinc fluoride; water; for 4h; Temperature;

Reference yield: 88.0%

m-Chlorobenzoyl chloride (618-46-2) → 3-chloro-benzenecarboperoxoic acid (937-14-4)

Guidance literature:

With potassium hydroxide; 1-hydroxyethylene-(1,1-diphosphonic acid); dihydrogen peroxide; In methanol; water; at 17 - 18 ℃; Product distribution; dependence of the purity of the product on the ratio of the solvent components, m-CBC:KOH and m-CBC:H₂O₂ ratios, stirring rates, nature and concentration of phosphorus-containing stabilizers and reactions temperatures;

Reference yield: 87.5%

3-chlorobenzoate (535-80-8) → 3-chloro-benzenecarboperoxoic acid (937-14-4)

Guidance literature:

With potassium peroxomonosulphate; N-benzyl-N,N,N-triethylammonium chloride; In diethyl ether; water; at 20 ℃; for 15h;

upstream raw materials:

m-Chlorobenzoyl chloride

3-chlorobenzoate

4-Bromothiophen-2-aldehyde

Dimethyldisulphide

Downstream raw materials:

N,N-dimethyl-4-(phenyl-trans-azo)-aniline-N-oxide

α-Chlorpropionyl-m-chlorbenzoylperoxid

1,3-dimethylparabanic acid

5-chloro-1,3-dimethyluracil

Refernces

• 1、 -. "Method for preparing m-chloroperoxybenzoic acid by utilizing phase transfer catalysis". Paragraph 0026-0033. . Retrieved 2020/05/02.
• 2、 Zhou, Weiyou,Chen, Yong,Qian, Junfeng,Sun, Fu’an,He, Mingyang,Chen, Qun. "Copper Tetrasulfophthalocyanine Intercalated Hydrotalcite as an Efficient Bifunctional Catalyst for the Baeyer–Villiger Oxidation". . p. 2157 - 2164. Retrieved 2016/10/18.