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3-Chloroperoxybenzoic acid

Chemical Properties Uses

CAS No.937-14-4
Chemical Name:3-Chloroperoxybenzoic acid
CBNumber:CB4259408
Molecular Formula:C7H5ClO3
Formula Weight:172.57
MOL File:937-14-4.mol

3-Chloroperoxybenzoic acid Property

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
Odor slight pungent odor
PH 4.5@25 °C (saturated aq. sol)
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)
UNSPSC Code 12352302
NACRES NA.22

Safety

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
F :4.4
TSCA :Yes
HazardClass :5.2
PackingGroup :II
HS Code :29163990

NFPA 704:

	1
3		3
	OX

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H242-H315-H317-H319-H335
Precautionary statements P210-P235-P280-P302+P352-P370+P378-P410

3-Chloroperoxybenzoic acid Price More Price(10)

Brand: Sigma-Aldrich(India)
Product number: 273031
Product name : 3-Chloroperbenzoic acid
Purity: ≤77%
Packaging: 25G
Price: ₹2280
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 273031
Product name : 3-Chloroperbenzoic acid
Purity: ≤77%
Packaging: 100G
Price: ₹4540
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 273031
Product name : 3-Chloroperbenzoic acid
Purity: ≤77%
Packaging: 500G
Price: ₹17380
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 273031
Product name : 3-Chloroperbenzoic acid
Purity: ≤77%
Packaging: 1KG
Price: ₹50725.95
Updated: 2022/06/14
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Brand: ottokemi
Product number: C 2142
Product name : meta-Chloroperoxybenzoic acid
Purity: 50-55%
Packaging: 100gm
Price: ₹2061
Updated: 2022/05/26
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3-Chloroperoxybenzoic acid Chemical Properties,Usage,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:
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.
reaction suitability reagent type: oxidant
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.]