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3-Chloroperoxybenzoic acid

CAS No.
937-14-4
Chemical Name:
3-Chloroperoxybenzoic acid
Synonyms
M-CPBA;M-CHLOROPERBENZOIC ACID;3-CHLOROPERBENZOIC ACID;M-CHLOROPEROXYBENZOIC ACID;3-chlorobenzoperoxoic acid;3-Chlorobenzenecarboperoxoic acid;3-Chloroperoxybenzoic Acid (MCPBA);3-ChL;M-Chloroperoxybenzoic;65.0%(T)
CBNumber:
CB4259408
Molecular Formula:
C7H5ClO3
Molecular Weight:
172.57
MDL Number:
MFCD00002127
MOL File:
937-14-4.mol
MSDS File:
SDS
Last updated:2023-11-20 17:31:36

3-Chloroperoxybenzoic acid Properties

Melting point 69-71 °C(lit.)
Boiling point 244.67°C (rough estimate)
Density 0.56
vapor pressure 0.373Pa at 25℃
refractive index 1.4580 (estimate)
storage temp. 2-8°C
solubility Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
pka 7.57 (in water @ 25 °C)
form Moist Powder
color White
PH 4.5@25 °C (saturated aq. sol)
Odor slight pungent odor
Water Solubility insoluble
Decomposition >88 °C
BRN 608317
Stability Strong oxidizing agent - contact with combustible material may cause fire. May be shock or heat sensitive. Incompatible with organic materials, strong reducing agents.
InChIKey NHQDETIJWKXCTC-UHFFFAOYSA-N
LogP 1.03 at 25℃
CAS DataBase Reference 937-14-4(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII G203D4H1RB
NIST Chemistry Reference 3-Chloroperbenzoic acid(937-14-4)
EPA Substance Registry System Benzenecarboperoxoic acid, 3-chloro- (937-14-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS02,GHS07
Signal word  Danger
Hazard statements  H242-H315-H317-H319-H335
Precautionary statements  P210-P235-P280-P302+P352-P370+P378-P410
Hazard Codes  O,Xi,C
Risk 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
RIDADR  UN 3106 5.2
WGK Germany  3
RTECS  SD9470000
4.4
TSCA  Yes
HazardClass  5.2
PackingGroup  II
HS Code  29163990
NFPA 704
1
3 3
OX

3-Chloroperoxybenzoic acid price More Price(22)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 273031 3-Chloroperbenzoic acid ≤77% 937-14-4 1kg $642 2024-03-01 Buy
Sigma-Aldrich 273031 3-Chloroperbenzoic acid ≤77% 937-14-4 10kg $2048 2024-03-01 Buy
Alfa Aesar L00286 3-Chloroperoxybenzoic acid, 50-55%, cont. ca 10% 3-chlorobenzoic acid, balance water 937-14-4 25g $34.1 2021-12-16 Buy
Alfa Aesar L00286 3-Chloroperoxybenzoic acid, 50-55%, cont. ca 10% 3-chlorobenzoic acid, balance water 937-14-4 100g $95.2 2021-12-16 Buy
Sigma-Aldrich 273031 3-Chloroperbenzoic acid ≤77% 937-14-4 25g $48.5 2024-03-01 Buy
Product number Packaging Price Buy
273031 1kg $642 Buy
273031 10kg $2048 Buy
L00286 25g $34.1 Buy
L00286 100g $95.2 Buy
273031 25g $48.5 Buy

3-Chloroperoxybenzoic acid Chemical Properties,Uses,Production

Chemical Properties

3-chloroperoxybenzoic acid is white powdery crystals. Melting point is 92-94°C (decomposed). It is almost insoluble in water, but soluble in ethanol, ethers, chloroform, and dichloroethane. It is thermally stable and has an annual decomposition rate of less than 1% at room temperature. The decomposition rate is accelerated in the liquid state. 3-Chloroperbenzoic acid is sensitive to heat and shock, and pure solid. 3-Chloroperbenzoic acid is flammable and potentially explosive. It contains a weak –O–O– bond and a nucleophilic OH group, that makes it versatile oxidative and easily breakable.

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.

Chemical Properties

White moist powder

Uses

Effective oxidant for epoxidizing di-, tri-, and tetra-substituted olefins.

Uses

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.

Definition

ChEBI: 3-chloroperbenzoic acid is a peroxy acid and a member of monochlorobenzenes.

Reactions

3-Chloroperoxybenzoic acid (MCPBA) is one of the most popular oxidation reagent in organic synthesis, because of its outstanding performance in terms of:
reactivity, combined with reducing the number of reaction steps in classical synthetic routes,
regio- and stereoselectivity,
protection of functional groups mostly not required,
high purity and yields.
Its literature covers a huge area of different syntheses and below reaction equations just can be a brief overview of its interesting applications:
3-Chloroperoxybenzoic acid Reactions

Synthesis Reference(s)

Synthetic Communications, 19, p. 1271, 1989 DOI: 10.1080/00397918908054534

General Description

3-Chloroperoxybenzoic acid is sensitive to heat. Storage of 3-Chloroperoxybenzoic acid must be done so with stringent temperature control measures. It's explosion hazard is also mitigated by mixing the peroxide in a solvent slurry.

Reactivity Profile

May explode from heat, shock, friction or contamination. May ignite combustibles (wood, paper, oil, clothing, etc.). May be ignited by heat, sparks or flames.

Purification Methods

Recrystallise MCPBA from CH2Cl2 [Traylor & Mikztal J Am Chem Soc 109 2770 1987]. Peracid of 99+% purity can be obtained by washing commercial 85% material with phosphate buffer pH 7.5 and drying the residue under reduced pressure. Alternatively the peracid can be freed from m-chlorobenzoic acid by dissolving 50g/L of *benzene and washing with an aqueous solution buffered at pH 7.4 (NaH2PO4/NaOH) (5 x 100mL). The organic layer is dried over MgSO4 and carefully evaporated under vacuum. Necessary care should be taken in case of EXPLOSION. The solid is recrystallised twice from CH2Cl2/Et2O and stored at 0o in a plastic container as glass catalyses the decomposition of the peracid. The acid is assayed iodometrically. [Schwartz & Blumbrgs J Org Chem 29 1976 1964, Bortolini et al. J Org Chem 52 5093 1987, McDonald et al. Org Synth Coll Vol VI 276 1988, Beilstein 9 IV 972.]

618-48-4
937-14-4
Synthesis of 3-Chloroperoxybenzoic acid from 3-CHLOROBENZAMIDE
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View Lastest Price from 3-Chloroperoxybenzoic acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
3-Chloroperoxybenzoic acid pictures 2024-01-02 3-Chloroperoxybenzoic acid
937-14-4
US $60.00-600.00 / kg 10kg 0.99 20tons Zibo Hangyu Biotechnology Development Co., Ltd
3-Chloroperoxybenzoic acid pictures 2023-11-20 3-Chloroperoxybenzoic acid
937-14-4
US $0.00 / kg 1kg 89% According to customer's requirements Changzhou waston chemical technology Co.,Ltd
3-Chloroperoxybenzoic acid pictures 2023-08-29 3-Chloroperoxybenzoic acid
937-14-4
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
3-CHLOROPEROXYBENZOIC ACID 3-Chloroperoxy benzoic acid(more than 57% but not more than 86%,with 3-chorobenzoic acid) 3-Chloroperoxybenzoic acid, balance 3-Chlorobenzoic acid and water, 70-75% 3-Chloroperoxybenzoic acid, 70 - 75%, (balance 3-chlorobenzoic acid and water) 3-Chlorobenzeneperoxycarboxylic acid 3-Chloroperoxybenzoic Acid (contains min. 17% Water and min. 6% 3-Chlorobenzoic Acid) 3-Chloroperoxybenzoic Acid (contains ca. 30% Water) 3-Chloroperoxybenzoic acid ,75% 3-Chloroperbenzoic acid,3-Chloroperoxybenzoic acid, MCPBA 3-Chloroperoxybenzoi Chloroperoxybenzoic 3-chloroperoxybenzic acid/Mcpba 3-Chloroperbenzoic Acid (Technical Grade, 70-75%, wet with water) 3-CHLOROPERBENZOICACIDM-CHLOROPERBENZOICACID70-75% M-CHLOROBENZOICACIDNOMORETHAN10% WATER15-22% M-cholroperoxbenzoic acid 3-chloro-benzenecarboperoxoicaci 3-chlorobenzenecarboperoxoicacid Benzenecarboperoxoic acid, 3-chloro- m-chloro-peroxybenzoicaci Perbenzoic acid, m-chloro- Peroxybenzoic acid, m-chloro- 3-Choroperoxybenzoic acid m-choroperoxybenzoic acid 3-CHLOROPEROXYBENZOIC ACID, 77% MAX. metaChloro Perbenzoic Acid 3-Chloroperoxybenzoic acid, tech., wet with water, 50-55% 3-Chloroperoxybenzoicacid,tech.70-77%,wetwithwater M-CHLOROPERBENZOIC ACID (MCPBA) M-CHLOROPEROXYBENZOIC ACID (M-CPBA) 3-Chloroperoxyb 3-Chloroperoxybenzoic acid, balance 3-Chlorobenzoic acid and water, 70-75% 100GR 3-Chloroperoxybenzoic acid, balance 3-Chlorobenzoic acid and water, 70-75% 1KG 3-Chloroperoxybenzoic acid, balance 3-Chlorobenzoic acid and water, 70-75% 25GR M-Chloroperoxobenzoic Acid NSC 97094 Chloroperoxybenzoicacid 3-Chloroperbenzoic acid <=77% Between chlorine acid peroxide 3-Chloroperoxybenzoic acid, tech grade 3-Chloroperbenzoic acid(MCPBA) m-Chloroperbenzoic acid m-CPBA MCPBA 3-Chloroperoxybenzoic acid, 70 - 75% 3-CHLOROPEROXYBENZOIC ACID, 50-55% 3-CHLOROPEROXYBENZOICACID,TECHNICAL CHLOROPERBENZOICACID META-CHLOROPEROXYBENZOICACID 3-Chloroperoxybenzoic acid, tech. ca 70-75%, wet with water 3-Chloroperoxybenzoic acid, 50-55%, cont. ca 10% 3-chlorobenzoic acid, balance water Chloroperoxybenzoic acid, 3- 3-chloroperoxybenzoic acid, 58-86%, with >=14% inert M-CHLORO BENZOYL HYDROPEROXIDE 3-Chloroperoxybenzoic acid[57% < content < 86%, inert solid content < 14%.] 3-Chloroperoxybenzoic acid[Content < 57%, inert solid content < 3%, water content < 40%.] 3-Chloroperoxybenzoic acid [Content < 77%, inert solid content (> 6%, water content (> 17%)] 3-Chlorperbenzoesure Methoxyacetic acid(M-CPBA) oroperoxybenzoic acid 3-Chloroperoxybenzoic Acid (contains ca. 30% Water)>