7454-72-0

Basic information

• Product Name: 4-bromo-N-(4-methoxyphenyl)benzenesulfonamide
• Synonyms: 4-bromo-N-(4-methoxyphenyl)benzenesulfonamide
• CAS NO: 7454-72-0
• Molecular Formula: C₁₃H₁₂BrNO₃S
• Molecular Weight: 342.20828
• Mol File: 7454-72-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 454.6°Cat760mmHg
• Flash Point: 228.7°C
• Appearance: /
• Density: 1.564g/cm³
• Vapor Pressure: 1.89E-08mmHg at 25°C
• Refractive Index: 1.631
• CAS DataBase Reference: 4-bromo-N-(4-methoxyphenyl)benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromo-N-(4-methoxyphenyl)benzenesulfonamide(7454-72-0)
• EPA Substance Registry System: 4-bromo-N-(4-methoxyphenyl)benzenesulfonamide(7454-72-0)

Safety Data

• Hazardous Substances Data: 7454-72-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H12BrNO3S/c1-18-12-6-4-11(5-7-12)15-19(16,17)13-8-2-10(14)3-9-13/h2-9,15H,1H3

Upstream product

• 104-94-9 4-methoxy-aniline 
• 98-58-8 4-bromobenzenesulfonyl chloride 
• 95-14-7 1,2,3-Benzotriazole 

Downstream Products

• 1022868-47-8 4-bromo-N-(4-methoxyphenyl)-N-methylbenzenesulfonamide 
• 1360059-36-4 C₂₃H₂₁BrN₂O₃S 
• 1360059-35-3 C₂₂H₁₉BrN₂O₃S 
• 647018-78-8 2-{[(4-bromo-benzenesulfonyl)-(4-methoxy-phenyl)-amino]-methyl}-acrylic acid ethyl ester 

Relevant articles and documents

Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides

Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.

Inhibition of mutated isocitrate dehydrogenase 1 in cancer

Background: R132H mutation of isocitrate dehydrogenase 1 (IDH1) is found in ~75% of low-grade gliomas and secondary glioblastomas as well as in several other types of cancer. More chemotypes of inhibitors of IDH1(R132H) are therefore needed. Objective: The study aimed to develop a new class of IDH1(R132H) inhibitors as potent antitumor agents. Method: A biochemical assay was developed to find inhibitors of IDH1(R132H) mutant enzyme. Chemical synthesis and structure-activity relationship studies were used to find compounds with improved potency. Antitumor activities of selected compounds were evaluated. Results: A series of aromatic sulfonamide compounds was found to be novel, potent inhibitors of IDH1(R132H) with Ki values as low as 0.6 μM. Structure-activity relationships of these compounds are discussed. Enzyme kinetics studies showed that one compound is a competitive inhibitor against the substrate α-KG and a non-competitive inhibitor against the cofactor NADPH. Several inhibitors were found to have no activity against wild-type IDH1, showing a high selectivity. Two potent inhibitors exhibited strong activity against proliferation of BT142 glioma cells with IDH1 R132H mutation, while these compounds did not significantly affect the growth of glioma cells without IDH1 mutation. Conclusion: This novel series of IDH1(R132H) inhibitors have potential to be further developed for the treatment of glioma with IDH1 mutation.

Phosphine-catalyzed intramolecular Rauhut-Currier reaction: Enantioselective synthesis of hydro-2: H -indole derivatives

A highly enantioselective intramolecular Rauhut-Currier reaction catalyzed by a multifunctional chiral aminophosphine catalyst was reported. A series of hydro-2H-indole derivatives that bear an all-carbon quaternary center were obtained in high yields (up to 94%), and excellent diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). And this reaction could be performed on a gram scale using 2 mol% catalyst loading.