| 3-Chloroperoxybenzoic acid Description: MCPBA is a strong electrophilic oxidising agent. It is a white powder, easy to handle, flammable, hygroscopic, soluble in less-polar solvents like CH2Cl2,CHCl3, 1,2-DCE, EtOAc, EtOH, t-BuOH, Et2O and some nonpolar solvents like benzene, it is slightly soluble in hexane, CCl4 and insoluble in H2O. Pure MCPBA is shock-sensitive and can deflagrate, it is potentially explosive beyond 70-85% purity. Therefore the transport in airplanes with a content of > 72% is forbidden. Main pollution is 3-chlorobenzoic acid (10%) as well as for safety reasons water. Nevertheless, material of purity >70-85% is rarely available commercially, since the pure compound is not particularly stable. It shows 1% degradation per year at room temperature. It is widely used in organic chemistry to carry out a variety of chemical transformations such as oxidation of carbonyl compounds, iminoindolines, olefins, imines, alkanes, silyl enol ethers, N- and S-heterocyclic, active Methylene groups, fluoromethylated allylic bromides, cyclic acetals and N-substituted phthalimidines,etc.1a Besides these it also oxidizes selenides, furans and phosphates to selenoxides, pyranones and phosphates, respectively. It is superior to H2O2 and other oxidising agents because of its reactivity, steroselectivity, purity and yield of products.1b
MCPBA is versatile applicable as peracid for use in laboratories.
Main areas are the oxidation of
- aldehydes and ketones to esters (Bayer-Villiger-Oxidation)
- olefines to epoxides
- sulfides to sulfoxides and sulfones
- amines to nitroalkanes, nitroxides or N-oxides
However, for reasons of the atomic economy, the use of MCPBA in production should be avoided. The research concentrates within this area rather on the use of hydrogen peroxide in connection with suitable catalysts or in situ generated, simpler peracids, such as peracetic acid or on potassium peroxymonosulfate (Oxone). In many reactions MCPBA with an outstanding reactivity is however more selective than hydrogen peroxide and other peracids.
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