937-14-4 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 937-14-4 differently. You can refer to the following data:
1. 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.
2. White moist powder
Uses
Different sources of media describe the Uses of 937-14-4 differently. You can refer to the following data:
1. 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.
2. 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.
3. Effective oxidant for epoxidizing di-, tri-, and tetra-substituted olefins.
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.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 937-14-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,3 and 7 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 937-14:
(5*9)+(4*3)+(3*7)+(2*1)+(1*4)=84
84 % 10 = 4
So 937-14-4 is a valid CAS Registry Number.
InChI:InChI:1S/C7H5ClO3/c8-6-3-1-2-5(4-6)7(9)11-10/h1-4,10H
937-14-4Relevant articles and documents
Method for preparing m-chloroperoxybenzoic acid by utilizing phase transfer catalysis
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Paragraph 0026-0033, (2020/05/02)
The invention discloses a method for preparing m-chloroperoxybenzoic acid by utilizing phase transfer catalysis. The method comprises the following steps: dissolving m-chlorobenzoic acid in an organicsolvent, adding an aqueous acidic oxidant solution with a pH value of 1-4, carrying out an oxidation reaction under the action of a phase transfer catalyst, carrying out extraction separation to obtain an organic phase, drying, and separating out filter residues to obtain an organic solution containing m-chloroperoxybenzoic acid. The m-chloroperoxybenzoic acid is obtained by catalyzing the reaction of m-chlorobenzoic acid and an oxidant through the phase transfer catalyst, the raw materials are stable in properties, cheap and easy to obtain, the process is simple and easy to control, the solvent can be recycled, the product yield is high, the yield of the m-chloroperoxybenzoic acid can reach 82% or above, and large-scale industrial production is facilitated.
Synthetic method for drug intermediate m-chloroperbenzoic acid
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Paragraph 0016-0019; 0020-0023; 0024-0027, (2018/07/30)
The invention discloses a synthetic method for the drug intermediate m-chloroperbenzoic acid. The synthetic method comprises the following steps: adding m-chlorophenylacetamide and a sodium nitrate solution into a reaction vessel, controlling a stirring speed to be 230-260 rpm and a solution temperature to be 10-16 DEG C, adding a methyl n-butyl ether solution and a 1,4-butanediol solution, addingN-bromoacetamide in batches within 20-40 min, and continuing a reaction for 60-90 min; and then adding an aqueous solution and zinc fluoride powder, controlling a stirring speed to be 310-330 rpm, continue the reaction for 3-4 h, carrying out washing with a sodium chloride solution for 30-50 min, then carrying out washing with a 3-heptanol solution for 20-40 min, carrying out recrystallization ina nitroethane solution, and then carrying out dehydration with a dehydrating agent so as to obtain the finished m-chloroperoxybenzoic acid.
METHOD FOR PRODUCING AMIDE COMPOUND
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Page/Page column 25; 27, (2010/01/29)
Disclosed is a method for producing an amide compound represented by the formula (3) below and having an excellent control activity against a harmful arthropod, which is characterized in that an aniline compound represented by the formula (1) below and an aldehyde compound represented by the formula (2) below are reacted in a solvent in the presence of an oxidizing agent such as oxygen or a peroxide. (In the formulae below, R1, R2 and R3 independently represent a C1-C6 alkyl group which may be substituted by a halogen atom, or the like; and R4, R5, R6 and R7 independently represent a halogen atom or the like.)