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3-chloroperbenzoic acid

3-Chloroperbenzoic acid is an organic compound used in various chemical reactions and research applications.
It is a peracid derivative of benzoic acid, with a chlorine atom substituted at the 3-position of the benzene ring. 3-Chloroperbenzoic acid is commonly employed as an oxidizing agent, particularly in organic synthesis for the introduction of oxygen-containing functional groups.
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Most cited protocols related to «3-chloroperbenzoic acid»

All commercially available materials were purchased from the indicated suppliers and used without further purification. 4-thiouridine (s4U), and meta-chloroperoxybenzoic acid (mCPBA) were purchased from Alfa Aesar (Haverhill, MA). 4-thiouridine-5′-triphosphate (s4UTP) was purchased from TriLink BioTechnologies (San Diego, CA). 2,2,2-trifluoroethylamine (TFEA), sodium acetate, EDTA, Tris hydrochloride, acrylamide/bis-acrylamide 30% solution, phenol:chloroform:isoamyl alcohol (25:24:1), and actinomycin D were purchased from Sigma Aldrich (St. Louis, MO). Sodium periodate (NaIO4) and ammonium bicarbonate were purchased from Acros Organics (Geel, Belgium). Methane thiosulfonate biotin-XX (MTSEA-biotin-XX) was purchased from Biotium. Dynabeads MyOne Streptavidin C1 beads were purchased from Thermo Fisher Scientific. Agencourt RNAClean XP beads were purchased from Beckman Coulter (Brea, CA). Phusion HF PCR master mix and Dithiothreitol (DTT) were purchased from Thermo Fisher Scientific (Waltham, MA). Phosphate buffered saline (PBS) was purchased from AmericanBio (Natick, MA). Dulbecco's Modified Eagle Medium (DMEM), fetal bovine serum (FBS), Trizol reagent, TURBO DNase and SuperScript III Reverse Transcriptase were purchased from Life Technologies (Carlsbad, CA). KAPA Taq Ready Mix was purchased from Kapa Biosystems Inc (Wilmington, MA). DMSO-d6, penicillin-streptomycin (P/S) and 33 mm 0.45 μm PDVF syringe filters were purchased from EMD Millipore (Billerica, MA). ATCC MTT Cell Proliferation Assay kit was purchased from American Type Culture Collection (Manassas, VA). NotI HF restriction enzyme was purchased from New England Biolabs (Ipswich, MA). SMARTer Stranded Total RNA Kit (Pico Input) was purchased from Takara Bio USA (Mountain View, CA). Hypersil Gold 3 μm, 160 × 2.1 mm column was purchased from Thermo Fisher Scientific (Waltham, MA). K562 cells were a gift from the Slavoff Lab, Yale Department of Chemistry. T7 RNA polymerase was a gift from the Strobel Lab, Yale Department of Molecular Biophysics and Biochemistry.
Publication 2018
3-chloroperbenzoic acid 4'-thiouridine 5'-triphosphate Acrylamide ammonium bicarbonate bacteriophage T7 RNA polymerase Biological Assay Biotin Cell Proliferation Chloroform Dactinomycin Deoxyribonucleases Dithiothreitol DNA Restriction Enzymes Eagle Edetic Acid Fetal Bovine Serum Gold isopentyl alcohol K562 Cells methanethiosulfonate Penicillins Phenol Phosphates RNA-Directed DNA Polymerase Saline Solution Sodium Acetate sodium metaperiodate Streptavidin Streptomycin Sulfoxide, Dimethyl Syringes Thiouridine trifluoroethylamine trizol Tromethamine
HPLC-grade methanol, acetonitrile, juvenile hormone III, triphenylphosphine (TPP), 2,2′–dipyridyl disulfide (DPDS), citronellol and dichloromethane were obtained from Sigma-Aldrich (St. Louis, MO). Farnesoic acid (Echelon, Salt Lake City, UT), sodium sulfide nonahydrate (MP Biomedicals, Solon, OH), DBD-COCl (4-(N,N-Dimethylaminosulfonyl)-7-(N-chloroformylmethyl-N-methylamino)-2,1,3-benzoxadiazole) and AABD–SH (4-Acetamido-7-mercapto-2,1,3-benzoxadiazole) were from TCI-America (Portland, OR). JHB3 was a gift from Dr. Stephen Tobe and was synthesized from methyl farnesoate using m-chloroperbenzoic acid in dichloromethane [36] . Diagnostic ions used for identification of JHB III included m/z  = 300, 283, 265, 251 and 301 as reported by Yin et al. [37] .
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Publication 2012
3-chloroperbenzoic acid 4-(N-chloroformylmethyl-N-methyl)amino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole acetonitrile citronellol Diagnosis Disulfides farnesoic acid High-Performance Liquid Chromatographies Ions juvenile hormone III Methanol methyl 6,7-10,11-bis(epoxy)-3,7,11-trimethyl-2-dodecenoate Methylene Chloride methyl farnesoate Sodium Chloride sodium sulfide nonahydrate Solon triphenylphosphine
F8Cmpd-II, (DCHIm)F8Cmpd-II, and PImCmpd-II were synthesized as previously described.62 (link)–65 (link),72 High-valent iron(IV)-oxo complexes were generated by preparing a 3.0 mL 1:9 MeTHF:toluene solution (0.01 mM or 0.1 mM) of F8FeII or PImFeII in a 10 mm path length quartz Schlenk cuvette, which was then sealed with a rubber septum in the glovebox. The cuvette was then cooled in the cryostat chamber to −90 °C, and the solution was then allowed to thermally equilibrate (~10 min) before various reagents were added. The reduced iron(II) precursors were subjected to 1 equiv of mCPBA dissolved in toluene at −90 °C, forming the F8Cmpd-II or PImCmpd-II species after 5 min (denoted by a characteristic increase in the extinction coe-cient of the Q-band). Subsequently, 2 equiv of 1,5-dicyclohexylimidazole (DCHIm) dissolved in toluene, 2 equiv of sodium 3,5-dimethoxyphenolate (ArO), or 2 equiv of sodium imidazolate (Im) was added to F8Cmpd-II, resulting in a red shift in the Soret and Q-band, yielding (DCHIm)F8Cmpd-II, (ArO)F8Cmpd-II, or (Im)-F8Cmpd-II, respectively. Due to solubility issues, sodium 3,5-dimethoxyphenolate and sodium imidazolate were added in a 4:1 15-crown-5 ether:butyronitrile solution instead of in toluene.
One equivalent of 2,6-lutidinium triflate, prepared as previously described by Tilley and co-workers,95 (link) was added in butyronitrile to F8Cmpd-II or (DCHIm)F8Cmpd-II, generating F8Cmpd-II(LutH+) or (DCHIm)F8Cmpd-II(LutH+), respectively. Various ferrocene derivatives (Me10Fc, Me8Fc, Me2Fc, Fc, AcetylFc, DiacetylFc) or tris(4-bromophenyl)amine were added to F8Cmpd-II, (DCHIm)-F8Cmpd-II, F8Cmpd-II(LutH+), and (DCHIm)F8Cmpd-II(LutH+), wherein the reactions were monitored by UV−vis, 2H NMR, or Mössbauer spectroscopies. The absorbance at 784 nm was monitored for various concentrations of decamethylferrocenium BArF (0.025–0.29 mM) and at 779 nm for octamethylferrocenium BArF (0.025–0.20 mM), forming standard curves (Figures S30 and S31) to quantify the number of electrons transferred at the end of the reaction. See Supporting Information for further details.
Publication 2019
3-chloroperbenzoic acid 15-crown-5 Amines decamethylferrocenium derivatives Electrons Ethyl Ether Extinction, Psychological ferrocene Iron Quartz Rubber Sodium Spectroscopy, Mossbauer Toluene Tromethamine Workers
Methoprene (Service Chemical Inc., Germany), JH III (Sigma-Aldrich), and MF (Echelon) were purchased. JHB3 was synthesized from MF using m-chloroperbenzoic acid in dichloromethane (Sigma-Aldrich) [19 (link)]. For rescue of fertility of jhamt2, newly eclosed females were placed in vials with standard medium; after 24 hours, virgin females were topically treated with acetone-dissolved methoprene (0.5 μl × 10-3 M per female) [21 (link), 23 (link)]. For rescue of pupal lethality of Aug21>grim and jhamt2hmgcrRNAi, methoprene, JHB3, JH III, and MF (0.5 μl × 10-9~-2 M per larva) were dissolved in acetone and topically applied to the larvae at 96h AIW [14 (link), 20 (link), 21 (link), 31 (link), 33 ]. For inducing Kr-h1 expression in w1118 and Met27gce2.5k, fat body tissues were isolated at 96h AIW and treated with methoprene, JHB3, JH III, and MF (1×10-6 M; DMSO as a control) for 30 min. For testing the conversion of MF to other JHs, the jhamt2hmgcrRNAi larvae were topically treated with acetone or MF (0.5×10-2 μmol per larva) at 108h AEL, and the three sesquiterpenoids titers were measured at 3hAIW (about 24 hours after treatment).
For inducing Kr-h1 expression in Drosophila Kc cells cultured in Schneider’s medium, the cells were treated with methoprene, JHB3, JH III, and MF (1×10-11~-6 M; DMSO as a control) for 30 min [31 (link)]. Using the T7 RiboMAX Express RNAi System (Promega), dsRNAs of USP and EGFP (as a control) were synthesized. Reduction of gene expression by RNAi in Kc cells was performed by transfecting dsRNAs using Effectene at a final concentration of 1 μg/ml dsRNA. The transfected cells were cultured for 48 h and treated with MF (1×10-6 M; DMSO as a control) for 30 min [31 (link)].
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Publication 2015
3-chloroperbenzoic acid Acetone Aftercare Cells Culture Media Drosophila Effectene Females Fertility Gene Expression Larva Methoprene methyl 6,7-10,11-bis(epoxy)-3,7,11-trimethyl-2-dodecenoate Methylene Chloride Promega Pupa RNA, Double-Stranded RNA Interference Sesquiterpenes Sulfoxide, Dimethyl Tissue, Adipose
PhIP was purchased from Toronto Research Chemicals (Toronto, ON, Canada). 2-Amino-1-methyl-6-[2H5]-phenylimidazo[4,5-b]pyridine ([2H5]-PhIP, 99% isotopic purity) was a gift from Dr. Mark Knize and Dr. Kristen Kulp (Lawrence Livermore National Laboratory, Livermore, CA). Human serum albumin, trypsin, chymotrypsin, pronase E, leucine aminopeptidase, prolidase, meta-chloroperoxybenzoic acid, tert-butyl hydroperoxide, dimethyldioxirane and sodium periodate, and LC-MS grade formic were purchased from Sigma-Aldrich (St. Louis, MO). LC-MS grade solvents were purchased from Fisher Scientific (Pittsburgh, PA). All other chemicals were ACS grade, and purchased from Sigma-Aldrich unless stated. Isolute C18 solid-phase extraction (SPE) columns (25 mg) were from Biotage (Charlotte, NC). Pierce Albumin Depletion Kit was from Thermo Fisher (Rockford, IL). Amicon Ultra centrifugal filter units (10,000 mw cutoff) were from Millipore (Billerica, MA). Human plasma was purchased from Bioreclamation LLC (Hicksville, NY).
Publication 2015
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine 3-chloroperbenzoic acid Albumins Chymotrypsin dimethyldioxirane Homo sapiens Isotopes Leucine Aminopeptidase Plasma proline dipeptidase Pronase E pyridine Serum Albumin, Human sodium metaperiodate Solid Phase Extraction Solvents tert-Butylhydroperoxide Trypsin

Most recents protocols related to «3-chloroperbenzoic acid»

Example 46

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A mixture of compound 46-1 (15 mg, 0.03 mmol, 1 eq) and m-CPBA (16.0 mg, 0.07 mmol, 2 eq) in DCM (2 mL) was stirred at 25° C. for 1 hr. LC-MS showed the desired compound was detected. The reaction mixture was diluted with H2O (6 mL) and the mixture was extracted with EA (8 mL*3). The combined organic phase was washed with brine (8 mL*2), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by prep-HPLC. The title compound (7 mg, 15.9 umol, 42.8% yield) was obtained as white solid. LCMS (ESI): RT=0.828 min, mass calc. for C22H20F3NO3S 435.46, m/z found 436.0 [M+H]+; 1H NMR (400 MHz, CD3OD) δ 1.31-1.34 (m, 1H) 1.32-1.32 (m, 1H) 1.32-1.32 (m, 1H) 3.29 (s, 3H) 4.24-4.33 (m, 1H) 7.77 (d, J=8.03 Hz, 2H) 7.92 (d, J=8.03 Hz, 2H) 7.97 (d, J=8.78 Hz, 1H) 8.01 (d, J=1.76 Hz, 1H) 8.10 (dd, J=8.78, 1.76 Hz, 1H) 8.55 (br d, J=7.28 Hz, 1H) 8.67 (d, J=1.51 Hz, 1H) 8.75 (s, 1H).

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Patent 2024
1H NMR 3-chloroperbenzoic acid brine fluoromethyl 2,2-difluoro-1-(trifluoromethyl)vinyl ether High-Performance Liquid Chromatographies Lincomycin naphthalene-2-carboxamide Vacuum

Example 12

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To a solution of trans-1-(4-(4-formyl-phenoxy)cyclohexyl)-3-(4-(trifluoromethoxy)phenyl)urea (344 mg, 0.82 mmol) in dichloromethane (DCM, 30 mL), meta-chloroperoxybenzoic acid (mCPBA) was added (316 mg of 70-75% with water) and allowed to stir overnight. The reaction was quenched by addition of a saturated solution of Na2SSO3. The organic layer was then extracted, washed with NaHCO3, dried with MgSO4 and evaporated to 5 mL. The resulting solution was diluted with EtOH (40 mL) and a solution of NaOH (7 mL of 6N) was added and allowed to stir for one hour. The solution was then evaporated to 10 mL and 1 N HCl was added until pH=2. Then product was then extracted with EtOAc, dried over MgSO4 and evaporated to afford the product (309 mg, 0.75 mmol, 91% yield). Before determining IC50, the resulting product was crystallized in MeOH/H2O. MP=160.6-166.3 (162.0) ° C. 1H 400 MHz NMR (DMSO-d6): 8.90 (s, 1H), 8.51 (s, 1H), 7.46 (d, J=9.2 Hz, 2H), 7.21 (d, J=8.8 Hz, 2H), 6.76 (d, J=9.2 Hz, 2H), 6.65 (d, J=8.4 Hz, 2H), 6.16 (d, J=8.0 Hz, 1H), 4.14-4.04 (b, 1H), 3.55-3.45 (b, 1H), 2.02-1.96 (b, 2H), 1.94-1.86 (b, 2H), 1.45-1.37 (m, 2H), 1.33-1.25 (m, 2H).

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Patent 2024
1H NMR 3-chloroperbenzoic acid Bicarbonate, Sodium Ethanol Methylene Chloride Sulfate, Magnesium Sulfoxide, Dimethyl Urea

Example 28

[Figure (not displayed)]

To a solution of compound 28-1 (120 mg, 0.3 mmol, 1 eq) in DCM (3 mL) was added m-CPBA (104.8 mg, 0.6 mmol, 2 eq). The mixture was stirred at 20° C. for 2 hr. LCMS showed reactant was consumed completely and ˜72% of desired compound was detected (m/z=436.0; RT: 0.82 min). The reaction mixture was diluted with DCM (30 mL). This solution was washed sequentially with saturated Na2SO3 (20 mL*2), NaHCO3 (20 mL*2), and brine (30 mL). The organic phase was dried over anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by prep-HPLC to give the title compound (45.8 mg, 0.1 mmol, 35.4% yield) as a white solid. LCMS (ESI): RT=0.825 min, mass calc. for C22H20F3NO3S 435.1, m/z found 436.0 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 9.14 (d, J=1.3 Hz, 1H), 8.58 (d, J=7.6 Hz, 1H), 8.38 (d, J=7.6 Hz, 1H), 8.06 (dd, J=1.6, 8.9 Hz, 1H), 8.00-7.91 (m, 3H), 7.78 (t, J=7.5 Hz, 3H), 4.26-4.10 (m, 1H), 3.49 (s, 3H), 1.23 (d, J=6.6 Hz, 6H).

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Patent 2024
1H NMR 3-chloroperbenzoic acid Bicarbonate, Sodium brine High-Performance Liquid Chromatographies Lincomycin naphthalene-2-carboxamide Sulfoxide, Dimethyl Vacuum

Example 27

[Figure (not displayed)]

To a solution of compound 27-1 (120 mg, 0.3 mmol, 1 eq) in DCM (3 mL) was added m-CPBA (47.1 mg, 0.3 mmol, 0.9 eq). The mixture was stirred at 20° C. for 2 hr. LCMS showed reactant was consumed completely and ˜83% of desired compound was detected (m/z=441.9; RT: 0.78 min). The reaction mixture was diluted with DCM (30 mL). This solution was washed sequentially with saturated Na2SO3 (20 mL*2), NaHCO3 (20 mL*2), and brine (30 mL). The organic phase was dried over anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by prep-HPLC to give the title compound (65.8 mg, 0.2 mmol, 52.7% yield) as a white solid. LCMS (ESI): RT=0.790 min, mass calc. for C22H20F3NO2S 419.1, m/z found 442.0 [M+Na]+; 1H NMR (400 MHz, DMSO-d6) δ 8.59 (d, J=7.6 Hz, 1H), 8.48 (d, J=1.3 Hz, 1H), 8.23 (d, J=7.5 Hz, 1H), 8.06 (dd, J=1.6, 9.0 Hz, 1H), 7.99-7.89 (m, 3H), 7.86-7.74 (m, 3H), 4.17 (m, 1H), 2.93 (s, 3H), 1.23 (dd, J=2.6, 6.6 Hz, 6H).

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Patent 2024
1H NMR 3-chloroperbenzoic acid Bicarbonate, Sodium brine High-Performance Liquid Chromatographies Lincomycin naphthalene-2-carboxamide Sulfoxide, Dimethyl Vacuum
Not available on PMC !

Example 45

[Figure (not displayed)]

A mixture of compound 45-1 (15 mg, 0.03 mmol, 1 eq) and m-CPBA (6.4 mg, 0.02 mmol, 0.8 eq), in DCM (2 mL) was stirred at 25° C. for 1 hr. LC-MS showed the desired compound was detected. The reaction mixture was diluted with H2O (6 mL) and the mixture was extracted with EA (8 mL*3). The combined organic phase was washed with brine (8 mL*2), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by prep-HPLC. The title compound (2 mg, 4.7 umol, 12.8% yield) was obtained as white solid. LCMS (ESI): RT=0.780 min, mass calc. for C22H20F3NO2S 419.46, m/z found 420.0 [M+H]+; 1H NMR (400 MHz, CD3OD) δ 1.21 (d, J=6.53 Hz, 6H) 2.85 (s, 3H) 4.18 (quin, J=6.59 Hz, 1H) 7.61-7.71 (m, 2H) 7.68-7.69 (m, 1H) 7.76-7.85 (m, 3H) 7.87-7.95 (m, 1H) 8.33 (s, 1H) 8.48 (d, J=1.26 Hz, 1H).

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Patent 2024
1H NMR 3-chloroperbenzoic acid brine fluoromethyl 2,2-difluoro-1-(trifluoromethyl)vinyl ether High-Performance Liquid Chromatographies Lincomycin naphthalene-2-carboxamide Quinine Vacuum

Top products related to «3-chloroperbenzoic acid»

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MCPBA is a laboratory reagent used in organic synthesis. It is a peroxycarboxylic acid that functions as an oxidizing agent. The core function of MCPBA is to facilitate various chemical transformations in the laboratory setting.
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Methanol is a clear, colorless, and flammable liquid that is widely used in various industrial and laboratory applications. It serves as a solvent, fuel, and chemical intermediate. Methanol has a simple chemical formula of CH3OH and a boiling point of 64.7°C. It is a versatile compound that is widely used in the production of other chemicals, as well as in the fuel industry.
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Acetonitrile is a colorless, volatile, flammable liquid. It is a commonly used solvent in various analytical and chemical applications, including liquid chromatography, gas chromatography, and other laboratory procedures. Acetonitrile is known for its high polarity and ability to dissolve a wide range of organic compounds.
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Ethanol is a clear, colorless liquid chemical compound commonly used in laboratory settings. It is a key component in various scientific applications, serving as a solvent, disinfectant, and fuel source. Ethanol has a molecular formula of C2H6O and a range of industrial and research uses.
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3-chloroperoxybenzoic acid is a chemical compound primarily used as an oxidizing agent in organic synthesis. It serves as a source of peroxybenzoic acid, which is a powerful oxidizing agent. The product is commonly utilized in laboratory settings for various chemical reactions and transformations.
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Acetonitrile is a highly polar, aprotic organic solvent commonly used in analytical and synthetic chemistry applications. It has a low boiling point and is miscible with water and many organic solvents. Acetonitrile is a versatile solvent that can be utilized in various laboratory procedures, such as HPLC, GC, and extraction processes.
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M-chloroperbenzoic acid is a chemical compound used as a laboratory reagent. It has the chemical formula C₇H₅ClO₃ and is a white crystalline solid. The compound serves as an oxidizing agent in various chemical reactions. Further details on its specific applications are not included to maintain an unbiased and factual approach.
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Dichloromethane is a clear, colorless, and volatile liquid commonly used as a laboratory solvent. It has a molecular formula of CH2Cl2 and a molar mass of 84.93 g/mol. Dichloromethane is known for its high solvent power and low boiling point, making it suitable for various laboratory applications where a versatile and efficient solvent is required.
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Meta-chloroperoxybenzoic acid (m-CPBA) is a chemical compound commonly used as an oxidizing agent in organic synthesis. It is a crystalline solid with a specific chemical structure and formula. m-CPBA is utilized in various laboratory applications requiring oxidation reactions, but a detailed description of its intended use is not provided.
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3-chloroperbenzoic acid is a chemical compound used as an oxidizing agent in various laboratory applications. It is a white crystalline solid with the molecular formula C₇H₅ClO₃. The compound serves as a source of peroxycarboxylic acid, which is useful for a range of synthetic and analytical procedures.

More about "3-chloroperbenzoic acid"

3-Chloroperbenzoic acid (MCPBA or m-CPBA) is a versatile organic compound widely used in chemical research and synthesis.
It is a peracid derivative of benzoic acid, with a chlorine atom substituted at the 3-position of the benzene ring.
This oxidizing agent is commonly employed for the introduction of oxygen-containing functional groups in organic reactions.
MCPBA can be utilized in a variety of applications, including organic synthesis, reagent preparation, and analytical procedures.
It is particularly useful for epoxidation, hydroxylation, and other oxidative transformations.
The compound is often used in conjunction with solvents like methanol, acetonitrile, ethanol, and dichloromethane to facilitate these chemical reactions.
Researchers can optimize their 3-chloroperbenzoic acid studies with PubCompare.ai, an AI-driven platform that helps compare and enhance the reproducibility of protocols from literature, preprints, and patents.
PubCompare.ai's AI-powered comparisons can identify the best protocols and prodcuts to take your 3-chloroperbenzoic acid research to the next level.
With PubCompare.ai, you can easily locate and compare MCPBA-related protocols, ensuring your experiments are efficient and reproducible.