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3-Chloroperoxybenzoic acid

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3-Chloroperoxybenzoic acid Basic information
3-Chloroperoxybenzoic acid Chemical Properties
  • Melting point:69-71 °C(lit.)
  • Boiling point:244.67°C (rough estimate)
  • Density 0.56
  • refractive index 1.4580 (estimate)
  • storage temp. 2-8°C
  • pka7.57 (in water @ 25 °C)
  • form Moist Powder
  • color White
  • Odorslight pungent odor
  • PH4.5@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.
  • InChIKeyNHQDETIJWKXCTC-UHFFFAOYSA-N
  • CAS DataBase Reference937-14-4(CAS DataBase Reference)
  • NIST Chemistry Reference3-Chloroperbenzoic acid(937-14-4)
  • EPA Substance Registry SystemBenzenecarboperoxoic acid, 3-chloro- (937-14-4)
Safety Information
MSDS
3-Chloroperoxybenzoic acid Usage And Synthesis
  • Chemical Properties3-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.
  • Uses3-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 PropertiesWhite moist powder
  • Reactions3-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 Description3-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 ProfileMay explode from heat, shock, friction or contamination. May ignite combustibles (wood, paper, oil, clothing, etc.). May be ignited by heat, sparks or flames.
  • Purification MethodsRecrystallise 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.]
3-Chloroperoxybenzoic acid Preparation Products And Raw materials
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