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273031 Aldrich

3-Chloroperbenzoic acid

≤77%

Synonym: 3-Chloroperoxybenzoic acid, MCPBA

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Properties

Related Categories Chemical Reagents, Chemical Synthesis, Development Quantities for Research, Oxidizing Agents, Peroxy Acids and Salts,
assay   ≤77%
mp   69-71 °C(lit.)
storage temp.   2-8°C

Description

Application

Effective oxidant for epoxidizing di-, tri-, and tetra-substituted olefins.

Other Notes

remainder 3-chlorobenzoic acid and water

Packaging

1 kg in poly bottle

10 kg in poly drum

25, 100, 500 g in poly bottle

Price and Availability

Suggested Laboratory Gloves


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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Hazard Codes (Europe) 
Risk Statements (Europe) 
Safety Statements (Europe) 
26-36/37
RIDADR 
UN 3106A1 5.2
WGK Germany 
3

Protocols & Articles

Peer-Reviewed Papers

References

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Direct, catalytic, and regioselective synthesis of 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles from N-oxides. Larionov OV, Stephens D, Mfuh A, et al. Org. Lett. 16(3), 864-7, (2014)

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CCl3CN: a crucial promoter of mCPBA-mediated direct ether oxidation. Kamijo S, Matsumura S, and Inoue M Org. Lett. 12(18), 4195-7, (2010)

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An N-bridged high-valent diiron-oxo species on a porphyrin platform that can oxidize methane. Kudrik EV, Afanasiev P, Alvarez LX, et al. Nature Chemistry 4(12), 1024-9, (2012)

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Cytochrome P450 compound I: capture, characterization, and C-H bond activation kinetics. Rittle J and Green MT Science 330(6006), 933-7, (2010)

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Spectroscopic studies of the oxidation of ferric CYP153A6 by peracids: Insights into P450 higher oxidation states. Spolitak T, Funhoff EG, and Ballou DP Arch. Biochem. Biophys. 493(2), 184-91, (2010)

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Iodobenzene catalyzed C-H amination of N-substituted amidines using m-chloroperbenzoic acid. Alla SK, Kumar RK, Sadhu P, et al. Org. Lett. 15(6), 1334-7, (2013)

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Iron(III) chloride catalyzed oxidative coupling of aromatic nuclei. Wang K, Lü M, Yu A, et al. J. Org. Chem. 74(2), 935-8, (2009)

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Iodomesitylene-Catalyzed Oxidative Cleavage of Carbon-Carbon Double and Triple Bonds Using m-Chloroperbenzoic Acid as a Terminal Oxidant K. Miyamoto, et al., J. Am. Chem. Soc. 131, 1382-1383, (2009)

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Cytochrome P450: the active oxidant and its spectrum. Rittle J, Younker JM, and Green MT Inorg. Chem. 49(8), 3610-7, (2010)

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Which oxidant is really responsible for P450 model oxygenation reactions? A kinetic approach. Franke A, Fertinger C, and van Eldik R Angew. Chem. Int. Ed. Engl. 47(28), 5238-42, (2008)

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Nickel(II) complexes of tripodal 4N ligands as catalysts for alkane oxidation using m-CPBA as oxidant: ligand stereoelectronic effects on catalysis. Balamurugan M, Mayilmurugan R, Suresh E, et al. Dalton Trans. 40(37), 9413-24, (2011)

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Monoepoxy octadecadienoates and monoepoxy octadecatrienoates 2: mass spectral characterization. Cui PH, Duke RK, Tattam BN, et al. Chem. Phys. Lipids 152(2), 65-70, (2008)

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Novel sulphur-rich BODIPY systems that enable stepwise fluorescent O-atom turn-on and H2O2 neuronal system probing. Singh AP, Lee KM, Murale DP, et al. Chem. Commun. (Camb.) 48(58), 7298-300, (2012)

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A catalytic version of hypervalent aryl-λ3-iodane-induced Hofmann rearrangement of primary carboxamides: iodobenzene as an organocatalyst and m-chloroperbenzoic acid as a terminal oxidant. Miyamoto K, Sakai Y, Goda S, et al. Chem. Commun. (Camb.) 48(7), 982-4, (2012)

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Synthesis of kifunensine thioanalogs and their inhibitory activities against HIV-RT and α-mannosidase. Chen H, Li R, Liu Z, et al. Carbohydr. Res. 365, 1-8, (2013)

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Lycopene epoxides and apo-lycopenals formed by chemical reactions and autoxidation in model systems and processed foods. Rodriguez EB and Rodriguez-Amaya DB J. Food Sci. 74(9), C674-82, (2009)

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Iminohydantoin lesion induced in DNA by peracids and other epoxidizing oxidants. Ye W, Sangaiah R, Degen DE, et al. J. Am. Chem. Soc. 131(17), 6114-23, (2009)

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Oxidative coupling of indoles with ethyl 2-(disubstituted amino)acetates: an approach to achieve indolylglycine derivatives. Xu Z, Yu X, Feng X, et al. J. Org. Chem. 77(16), 7114-8, (2012)

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Factors that affect the nature of the final oxidation products in "peroxo-shunt" reactions of iron-porphyrin complexes. Franke A, Wolak M, and van Eldik R Chemistry 15(39), 10182-98, (2009)

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Sequential directed epoxydation-acidolysis from glycals with MCPBA. A flexible approach to protected glycosyl donors. Marín I, Castilla J, Matheu MI, et al. J. Org. Chem. 76(23), 9622-9, (2011)

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Oxidative inactivation of protein tyrosine phosphatase 1B by organic hydroperoxides. Sanjib Bhattacharya et al Bioorg. Med. Chem. Lett. 18, 5856-9, (2008)

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A new family of color-tunable light-emitting polymers with high quantum yields via the controlled oxidation of MEH-PPV. Duncan TV and Park SJ J. Phys. Chem. B 113(40), 13216-21, (2009)

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Antiangiogenic resveratrol analogues by mild m-CPBA aromatic hydroxylation of 3,5-dimethoxystilbenes. Spatafora C, Basini G, Baioni L, et al. Nat. Prod. Commun. 4(2), 239-46, (2009)

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Asymmetric total synthesis and antiproliferative activity of goniothalamin oxide isomers. Marquissolo C, de Fátima A, Kohn LK, et al. Bioorg. Chem. 37(2), 52-6, (2009)

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Brominated thiophenes as precursors in the preparation of brominated and arylated anthraquinones. Thiemann T, Tanaka Y, and Iniesta J Molecules 14(3), 1013-31, (2009)

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A novel intermediate in the reaction of seleno CYP119 with m-chloroperbenzoic acid. Sivaramakrishnan S, Ouellet H, Du J, et al. Biochemistry 50(14), 3014-24, (2011)

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Oxycodone N-oxide. Sonar VN, Parkin S, and Crooks PA Acta Crystallogr. C 68(Pt 11), o436-8, (2012)

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Beil. 9,IV,972

Fieser 1,135 / Fieser 2,68 / Fieser 3,49 / Fieser 4,85 / Fieser 5,120 / Fieser 6,110 / Fieser 7,62 / Fieser 8,97 / Fieser 9,108 / Fieser 10,92 / Fieser 12,118 / Fieser 13,76 / Fieser 14,84 / Fieser 15,86 / Fieser 16,80 / Fieser 17,76

Aldrich MSDS 1, 438:B / FT-IR 1 (2), 191:B / NMR-Reference 2 (2), 188:C / RegBook 1 (2), 1785:N / Sax 6, 748 / Structure Index 1, 285:B:3

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