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GENERAL INFORMATION & PHYSICAL AND CHEMICAL PROPERTIES :

Molecular Structure :

Molecular Formula : C7H5ClO3
Molecular Weight : 172.57 g/mol
CAS No. : 937-14-4
Chemical Name : m-CHLOROPERBENZOIC ACID
INCI Name : m-Chloroperoxybenzoic Acid; m-CPBA; MCPBA;3-Chloroperoxybenzoic Acid
Description : White Moist Crystalline Powder
Assay (Iodometric) : 70 – 75 %. (w/w)
3-Chloro Benzoic Acid : Not more then 10 % (w/w)
Water by KF : 15 - 22 % (w/w)


MAIN AREAS OF REACTIONS
• Oxidation • Epoxidation • Cyclizing reaction • Baeyer-
villiger oxidation
• Carboxy-inversion reaction • Steroid amines to Nitro
Steroids

m-CPBA APPLIED SUCCESSFULLY IN VARIOUS INDUSTRIES LIKE
• Pharmaceutical • Pesticides • Herbicides • Bleach /
Detergent

Thermal Stability :Organic peroxides are thermally unstable substances,which may undergo self-accelerating decomposition. The lowest temperature at which self-accelerating decomposition of substance in the original packaging may occur is the self accelerating, Decomposition Temp. The SAD is determined on the basis of the heat accumulation storage Test. SADT : 55°C.

Major Decomposition Products : 3-Chlorobenzoic Acid and water

3-Chloroperoxybenzoic acid, MCPBA, meta-Chloroperbenzoic acid

 

 

 

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

 

 

TYPE Reactions

 

Prilezhaev Reaction
Rubottom Oxidation
Baeyer-Villiger Oxidation

 

J. Org. Chem., 63, 1390 (1998)

Epoxidation

 

March’s Advanced Organic
Chemistry, 5th Ed., Wiley, New
York (2001), p. 1051

S-Oxidation

 

Tetrahedron Asymmetry, 11,
3819 (2000)

 

Recent Literature

 

Use of a solvent with greater density than the fluorous phase is an alternative to the U-tube method in phase-vanishing reactions in cases where both reactants are less dense than the fluorous phase. This method has been successfully applied to the methylation of a phenol derivative with dimethyl sulfate and to the m-CPBA-induced epoxidation of alkenes, N-oxide formation from nitrogen-containing compounds, and S-oxide or sulfones formation from organic sulfides.
N. K. Jana, J. G. Verkade, Org. Lett. 2003, 5, 3787-3790.
N. K. Jana, J. G. Verkade, Org. Lett., 2003, 5, 3787-3790.
The results of a highly diastereoselective epoxidation of allylic diols derived from Baylis-Hillman adducts are reported.
R. S. Porto, M. L. A. A. Vasconcellos, E. Ventura, F. Coelho, Synthesis, 2005, 2297-2306.
Several amides were obtained in high yields by an efficient method from the corresponding imines which are readily prepared from aldehydes. This procedure involves the oxidation of aldimines with m-CPBA and BF3·OEt2. In this reaction, the product is strongly influenced by the electron releasing capacity of the aromatic substituent (Ar).
G. An, M. Kim, J. Y. Kim, H. Rhee, Tetrahedron Lett., 2003, 44, 2183-2186.
An efficient conversion of cyclic acetals to their corresponding hydroxy alkyl esters was demonstrated. This oxidation using MCPBA gave products in good to excellent yields.
J. Y. Kim, H. Rhee, M. Kim, J. Korean Chem. Soc., 2002, 46, 479-483.
Various α-tosyloxyketones were efficiently prepared in high yields from the reaction of ketones with m-chloroperbenzoic acid and p-toluenesulfonic acid in the presence of a catalytic amount of iodobenzene.
Y. Yamamoto, H. Togo, Synlett, 2006, 798-800.5
MCPBA is a versatile reagent for the oxidation of 4-methoxyphenyl- substituted fluorinated carbonyl compounds to the corresponding esters using 1,1,1,3,3,3-hexafluoro-2-propanol as cosolvent with CH2Cl2 and aqueous buffer (KH2PO4/NaOH) as an additive base under mild conditions.
Kobayashi, S.; Tanaka, H.; Amii, H.; Uneyama, K.Tetrahedron 2003, 59, 1547.
MCPBA is used along with phenyliodine(III) bis(trifluoroacetate) PIFA) for the synthesis of dienone lactones from phenyl ether derivatives.6 Here MCPBA acts as a co-oxidant which regenerates the hypervalent iodine(III) species after each cycle, thus making the reaction catalytic.
Burford, N.; Dyker, C.; Lumsden, M.; Decken, A. Angew.Chem. Int. Ed. 2005, 44, 6193.
Oxidation of cycloalkanes is carried out with MCPBA in MeCN catalyzed by Fe(III) chloride to form alkylhydroxyperoxide which partially decomposes to the corresponding more stable alcohol and ketone.
Shulpin, G.; Evans, H.; Mandelli, D.; Kozlov, Y.; Vallina,T.; Woitiski, C.; Jimenez, R.; Carvalho, W. J. Mol. Catal. A:Chem. 2004, 219, 255.
Trimethylsilylenol ethers are oxidized to a-hydroxy ketones by MCPBA. This reaction involves regioselective and stereoselective a-hydroxylation of ketones via a trimethylsilyl enol ether derivative.
Santos, R.; Brocksom, T.; Zanotto, R.; Brocksom, U. Molecules 2002, 7, 129.
It is used for the synthesis of 3-substituted pyrrolidin-4-ones from 4-aryl-1,2,5,6-tetrahydro pyridines by iterative synthetic operations using the combination of MCPBA and BF3·OEt2.
Chang, M.; Pai, C.; Lin, C. Tetrahedron Lett. 2006, 47,3641.
Fluoromethylated allenes can be synthesized from 2-phenylthioallylic bromide by treatment with 1.5 equivalents MCPBA in CH2Cl2 at reflux temperature for 1–2 h.
Han, H.; Kim, M.; Son, J.; Jeong, I. Tetrahedron Lett. 2006,47, 209.

 

The scope of its reactivity is illustrated in the following table.

 

Reactant

Product

Example

Ref.

Olefins

Expoxidesa

 

 

1-7

Cyclopropenes

a,ß-Unsaturated aldehydes and/or ketones

 

 

8,9

a,ß-Unsaturated ketones and esters

Epoxides

 

 

10

Disubstituted actylenes

Oxirenesb

 

 

11,12

Imines

Oxaziranes

 

 

13-16

Ketones (Baeyer-Villiger oxidation)

Esters

 

 

17-21

Acid Chlorides

Alcohols

 

 

22

Acids

Alcohols

 

 

23

Primary alkyl amines

Nitro alkenes

 

 

24

Primary aromatic amines

Aromatic nitroso compounds

 

 

25

Secondary amines

Nitroxides radicals

 

 

26

Tertiary amines

N-oxides

 

 

27

Nucleic acid components

N-oxide

 

 

28-31

N-substituted aziridines

Olefine

 

 

17-21

2-Pyridine-acetates

Corresponding glycolatesƒ

 

 

34

Sulfides

Sulfoxides
Or
solfonesg

 

 

35-40

Carbodiimides

Diaziridinones

 

 

41

Ketals

Ortho esters

 

 

42

Trimethylsilyl vinyl
and allyl systems

Trimethylsilyl epoxides (latent precursors to car-bonyl groups)

 

 

43-46

Iminoethers

Esters and hydroxylamines

 

 

47

a-Hydroxy ketones

Aldehydes and acids

 

 

48

Mono-, di-,
and
trimethoxybenz aldehydes

Formate esters

 

 

49

a-Diazoketones

a-Diketones

 

 

50

ß-Lactam acid chlorides

Aryl-ß-Lactam derivatives

 

 

51

Secondary alcohols

Ketones

 

 

52

Erythro thioether

Sulfones

 

 

53

Terminal olefines

Primary alcohols

 

 

54

Aromatics Hydrocarbons

Arene dioxides

 

 


meta-Chloroperoxybenzoic acid (mCPBA)

meta-Chloroperoxybenzoic acid (mCPBA) is a peroxycarboxylic acid used widely as an oxidant in organic synthesis. mCPBA is often preferred to other peroxy acids because of its relative ease of handling. The main areas of use are the conversion of ketones to esters (Baeyer-Villiger oxidation), epoxidation of alkenes (Prilezhaev reaction), oxidation of sulfides to sulfoxides and sulfones, and oxidation of amines to produce amine oxides.[1] mCPBA is a strong oxidizing agent that may cause fire upon contact with flammable material.

 

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