3-chloroperbenzoic acid
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»
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)].
Most recents protocols related to «3-chloroperbenzoic acid»
Example 46
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).
Example 12
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).
Example 28
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).
Example 27
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).
Example 45
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).
Top products related to «3-chloroperbenzoic acid»
More about "3-chloroperbenzoic acid"
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.