Screen

Profile

Layout

Direction

Menu Style

Cpanel

Profile

Synonyms : 3-Chloroperbenzoic acid, m-CPBA,
3-Chloroperoxybenzoic acid,
CAS No : 937-14-4
EU. NO. 213-322-3
Molecular Weight: 172.5658 g/mol
Molecular Formula: C7H5ClO3
Molecular Structure : INCI Name :-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 15 % (w/w)
Water by Kf15 - 22 % (w/w)

 

Versatile and most Convenient Oxidizing – Epoxidising Agent

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

SPECIFICATIONS FOR STABILITY STUDY:
In-house Specifications and test procedures are followed for stability study.

Stability Specifications:
Sr. No. Tests Specifications
01. Appearance White Moist Crystalline Powder
02. Assay 70 to 75 %
03. Free 3-Chloro Benzoic Acid Not more then 15.00 %
04. Water By Kf 15 - 22 %

STABILITY CONDITIONS:
Long term storage conditions

Organic Peroxides are unstable due to nature a loss of quality can be detected over a period of time to minimize the loss of quality. The storage of temp. is maximum 20°C. When stored under these recommended storage condition, MCPBA will remain as per our specification for a period if at least one year.

Temperature : 20ºC.

FREQUENCY OF TESTING:
Stability commitment:
The stability data will be updated on annual basis and will be provided as supplementary information to the regulatory authority / Party
3-Chloroperoxybenzoic acid is a strong oxidizing agent, which is comparable with other peracids.


3-Chloroperoxybenzoic acid, MCPBA, meta-Chloroperbenzoic acid

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.
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
55
l In nonconjugated dienes the more substituted double bond is selectively epoxidized.
l Oxirenes break down to ketones, carboxylic acids or esters depending on reaction conditions.
l The yields of nitroalkanes decrease in the order: tert-alkyl > sec-alkyl > n-alkyl.
l I.R. Subbaraman and co-workers21 reported that cytosine, adenine and their derivatives are oxidized to N-oxides while Uralic, thymine, guanosine and their derivatives give ring-cleavage products. However, M.R. Harden et al.22
l Indicated that N(1)-oxides were obtained from adenine, cytosine and Uralic derivatives while guanine derivatives yielded the N(3)-oxides.
l N-substituted zairidines are presumably oxidized to the corresponding N-oxides. This reaction is successfully used in the sterospecific deamination of N-alkylaziridines to olefins. . the 3- and 4-pyridyl isomers gave the corresponding N-oxides in high yields.
l Yields of sulfones or sulfoxides are excellent even in the presence of amino, 27 olefinic or acetylenic28 moiety.
REFERENCES:
(1a) Encyclopedia of Reagents for Organic Synthesis, Vol. 2; Paquette, L. A., Ed.; Wiley: Chichester, 1995, 1192.
(1b) International Electronic Conference on SyntheticOrganic Chemistry, Sept. 2000.ungetaggter Text Ende.
1. Paquette, L.A.; Barrett, J.H. Org. Syn. 1969, 49, 62.
2. Swern, D. Chem. Rev. 1949, 45,1.
3. Fieser, L.; Fieser, M. Reagents for Org. Syn. 1968, 1, 1136.
4. Haywood-Farmer, J.; Friedlander, B.T.; Hammond, L.M. J. Org. Chem. 1973, 38, 3145.
5. Anderson, W.K.; Veysoglu, T. ibid. 1973, 38, 2267.
6. Ikegami, Sl; et al. Tetrahedron Lett. 1980, 21, 3587.
7. Kende, A.S.; Blacklock, T.J. ibid. 1980, 21, 3119.
8. Ciabatton, J.; Kocienski, P.J. J. Am. Chem. Soc. 1969, 91, 6534.
9. Kocienski, P.J.; Ciabattoni, J. J. Org. Chem. 1974, 39, 388.
10. Schwartz, N.N.; Blumbers, J.H. ibid. 1964, 29, 1976.
11. Stille, J.K.; Whitehurst, D.D. J. Am. Chem. Soc. 1964, 86, 4871.
12. Ciabattoni, J.; Campbell, R.A.; Renner, C.A. ibid. 1970, 92, 3826.
13. Emmons, W.D. ibid. 1956, 78, 6208.
14. Padwa, A. ibid. 1965, 87, 4365.
15. Madan, V.; Clapp, L.B. ibid, 1969, 91, 6078.
16. Madan, V.; Clapp, L.B. ibid, 1970, 92, 4902.
17. Meinwald, J.; Tufariello, J.J.; Hurst, J.J. J. Org. Chem. 1964, 29, 2914.
18. Palmer, B.W.; Fry, A. J. Am. Chem. Soc. 1970, 92, 2580.
19. Syrkin, Y.K.; Moiseev, I.I. Russ. Chem. Rev. 1960, 29, 193.
20. Marshall, J.A.; Ellison, R.H. J. Org. Chem. 1975, 40, 2070.
21. Hudrlik, P.R.; et al. J. Am. Chem. Soc. 1980, 102, 6894.
22. Denney, D.B.; Sherman, N. J. Org. Chem. 1965, 30, 3760.
23. Rosen, P.; et. al. 166th National Meeting of the American Chemical Society, Chicago, IL, August, 1973, MEDI Abstr. 61.
24. Robinson, C.H.; Milewich, L.; Hofer, P. J. Org. Chem. 1966, 31, 524.
25. Terabe, S.; Konaka, R. J. Chem. Soc., Perkin Trans. 2 1973, 369.
26. Chapelet-Letourneux, G.; Lemaire, H.; Rassat, A. Bull. Soc. Chim. France 1965, 3283.
27. Craig, J.C.; Purushotharnan, K.K. J. Org. Chem. 1970, 35, 1721.
28. Delia, T.J.; Olsen, J.J.; Brown, G.B. ibid. 1965, 30, 2766.
29. Subbaraman, L.R.; Subbaraman, J.; Behrman, E.J. Biochemistry 1969, 8, 2059.
30. Harnden, M.R.; Brown, A.G.; Verg Hodge, R.A. J. Chem. Soc., Perkin Trans. 1 1973, 333.
31. Deady, L.W. Synth. Commun. 1977, 7, 509.
32. Padwa, A.; Hamilton, L. J. Org. Chem. 1966, 31, 1995.
33. Heine, H.W.; Myers, J.D.; Peltzer III, F.T. Angew, Chem., Int. Ed. Engl. 1970, 9, 374.
34. Skattebol, L.; Boulette, B. J. Org. Chem. 1969, 34, 4150.
35. Curci, R.; Giovine, A.; Modena, G. Tetrahedron 1966, 22, 1235.
36. Brown, D.J.; Ford, P.W. J. Chem. Soc. (C) 1969, 2720.
37. Russell, G.A.; Ochrymowycz, L.A. J. Org. Chem. 1970, 35, 2106.
38. Trost, B.M.; Mao, M.R.T. Tetrahedron Lett. 1980, 21, 3523.
39. Ager, D.J. ibid. 1980, 21, 4759.
40. Heissler, D.; Riehl, J.-J. ibid. 1980, 21, 4707.
41. Greene, F.D.; Bergmark, W.R.; Pazos, J.F. J. Org. Chem. 1970, 35, 2813.
42. Gaoni, Y. J. Chem. Soc. (C) 1968, 2934.
43. Stork, G.; Jung, M.E. J. Am. Chem. Soc. 1974, 96, 3682.
44. Pennanen, S.I. Tetrahedron Lett. 1980, 21, 657.
45. Paquette, L.A.; et al. J. Org. Chem. 1980, 45, 3028.
46. Magnus, P.; Ehlinger, E. J. Am. Chem. Soc. 1980, 102, 5004.
47. Aue, D.H.; Thomas, D. Tetrahedron Lett. 1973, 1807.
48. Greibrokk. T. Acta Chem. Scand. 1973, 27, 3365.
49. Sargent, M.V.; Godfrey, I.M. J. Chem. Soc., Perkin Trans. 1 1974, 1353.
50. Curci, R.; DiFuria, F.; Ciabattoni, J.; Concannon, P.W. J. Org. Chem. 1974, 39, 3295.
51. Bose, A.K.; Kapur, J.C. Tetrahedron Lett. 1973, 1811.
52. Cella, J.A.; Kelley, J.A.; Kenehan, E.F. J. Org. Chem. 1975, 40, 1860.
53. Alcudia, F.; et al. J. Chem. Soc., Perkin Trans. 2 1979, 564.
54. Kumada, M.; Tamao, K.; Kakui, T. J. Am. Chem. Soc. 1978, 100, 2268.
55. Griffin, G.W.; Ishikawa, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 171.

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.

 

Read more

Contact us

  • Phone: +917965126847
  • Raju Patel: +919825890617
  • Samir Patel: +919712990617
  • Email: rvpatel@umabiotech.com
  • Address: UMA Enterprise
    40, Ilaben Patel Estate, Nr. Aarvee
    Denim Narol-Sarkhej Highway,
    Narol, Ahmedabad – 392405,
    Gujarat, India