4284-50-8

Usage

Uses

Used in Pharmaceutical Industry:
N-(4-BROMOPHENYL)METHANESULFONAMIDE, 97% is used as a pharmaceutical intermediate for the synthesis of various pharmaceutical products. Its unique chemical structure, including a bromine atom and a sulfonamide group, makes it a valuable component in the development of new drugs.
Used in Organic Chemistry:
N-(4-BROMOPHENYL)METHANESULFONAMIDE, 97% is used as a reagent in the preparation of other organic compounds. Its versatility in chemical reactions allows for the synthesis of a wide range of organic molecules, contributing to the advancement of organic chemistry.
Used in Medicinal Chemistry and Drug Discovery:
N-(4-BROMOPHENYL)METHANESULFONAMIDE, 97% is utilized in the field of medicinal chemistry and drug discovery. Its potential applications in these areas include the development of new therapeutic agents and the enhancement of existing drug formulations.
Used in Research and Development:
With a high purity level of 97%, N-(4-BROMOPHENYL)METHANESULFONAMIDE, 97% is suitable for use in research and development. Its high quality makes it an ideal candidate for experiments and studies aimed at understanding its properties and potential applications.
Used in Industrial Processes:
N-(4-BROMOPHENYL)METHANESULFONAMIDE, 97% is also used in industrial processes that require high-quality chemicals. Its purity and stability make it a reliable choice for large-scale production and manufacturing.

InChI:InChI=1/C7H8BrNO2S/c1-12(10,11)9-7-4-2-6(8)3-5-7/h2-5,9H,1H3

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 106-40-1 4-bromo-aniline 
• 191043-81-9 N-(4-bromophenyl)-N-(methylsulfonyl)methanesulfonamide 
• 75-75-2 methanesulfonic acid 
• 7143-01-3 Methanesulfonic anhydride 
• 62-53-3 aniline 
• 5467-74-3 4-Bromophenylboronic acid 
• 624-90-8 Methanesulfonyl azide 
• 1197-22-4 N-phenylmethanesulfonamide 

Downstream Products

• 22729-44-8 N-(4-Bromo-phenyl)-N-(1,1,2,2-tetrachloro-2-fluoro-ethylsulfanyl)-methanesulfonamide 
• 333383-76-9 N-(4-bromo-phenyl)-N-(3-oxo-propyl)-methanesulfonamide 
• 99980-38-8 N-(4-bromophenyl)-N-methylmethanesulfonamide 
• 616880-14-9 N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonamide 
• 1352244-14-4 N-(2-amino-4-vinylphenyl)-N-methylmethanesulfonamide 
• 1078137-12-8 N-(2-amino-4-bromophenyl)-N-methylmethanesulfonamide 
• 1352244-37-1 N-(2-{2-[5-bromo-2-methoxy-4-(4-methylpiperazin-1-yl)phenylamino]-5-chloropyrimidin-4-ylamino}-4-vinylphenyl)-N-methylmethanesulfonamide 
• 1352244-34-8 N-(4-bromo-2-{5-chloro-2-[4-(4-methylpiperazin-1-yl)-3-vinylphenylamino]pyrimidin-4-ylamino}phenyl)-N-methylmethanesulfonamide 
• 1352244-22-4 N-[2-(2,5-dichloropyrimidin-4-ylamino)-4-vinylphenyl]-N-methylmethanesulfonamide 
• 1352244-20-2 N-[4-bromo-2-(2,5-dichloropyrimidin-4-ylamino)phenyl]-N-methylmethanesulfonamide 
• 1352244-86-0 N-methyl-N-(2-nitro-4-vinylphenyl)methanesulfonamide 
• 1078136-96-5 N-(4-bromo-2-nitrophenyl)-N-methylmethanesulfonamide 
• 1352244-85-9 N-(4-bromo-2-nitrophenyl)methanesulfonamide 
• 1246375-60-9 C₁₆H₂₄BrNO₄S 

Relevant academic research and scientific papers

Design and synthesis of 1H-pyrazolo[3,4-b]pyridines targeting mitogen-activated protein kinase kinase 4 (MKK4) - A promising target for liver regeneration

Currently, the therapeutic options for treatment of liver failure are very limited. As mitogen-activated protein kinase kinase 4 (MKK4) has recently been identified by in vivo RNAi experiments to be a major regulator in hepatocyte regeneration, we pursued the development of a small molecule targeting this protein kinase. Starting from the approved BRAFV600E inhibitor vemurafenib (8), that showed a high off-target affinity to MKK4 in an initial screening, we followed a scaffold-hopping approach, changing the core heterocycle from 1H-pyrrolo[2,3-b]pyridine to 1H-pyrazolo[2,3-b]pyridine (10). Affinity to MKK4 could be conserved while the selectivity against off-target protein kinases was slightly improved. Further modifications led to 58 and 59 showing high affinity to MKK4 in the low nanomolar range and excellent selectivity profile from mandatory multiparameter-optimization for the essential anti-targets (MKK7, JNK1) and off-targets (BRAF, MAP4K5, ZAK) in the MKK4 pathway. Herein we report the first selective MKK4 inhibitors in this class.

Meta Selective C-H Borylation of Sterically Biased and Unbiased Substrates Directed by Electrostatic Interaction

An electrostatically directed meta borylation of sterically biased and unbiased substrates is described. The borylation follows an electrostatic interaction between the partially positive and negative charges between the ligand and substrate. With this strategy, it has been demonstrated that a wide number of challenging substrates, especially 4-substituted substrates, can selectively be borylated at the meta position. Moreover, unsubstituted substrates also displayed excellent meta selectivity. The reaction employs a bench-stable ligand and proceeds at a milder temperature, precluding the need to synthesize a bulky and sophisticated ligand/template.

Continuous-Flow Electrosynthesis of Benzofused S-Heterocycles by Dehydrogenative C?S Cross-Coupling

Reported herein is the synthesis of benzofused six-membered S-heterocycles by intramolecular dehydrogenative C?S coupling using a modular flow electrolysis cell. The continuous-flow electrosynthesis not only ensures efficient product formation, but also obviates the need for transition-metal catalysts, oxidizing reagents, and supporting electrolytes. Reaction scale-up is conveniently achieved through extended electrolysis without changing the reaction conditions and equipment.

PROTEIN KINASE MKK4 INHIBITORS FOR PROMOTING LIVER REGENERATION OR REDUCING OR PREVENTING HEPATOCYTE DEATH

The invention relates to pyrazolo-pyridine compounds which inhibit mitogen-activated protein kinase kinase 4 (MKK4) and in particular, selectively inhibit MKK4 over protein kinases JNK1 and MKK7. The compounds are useful for promoting liver regeneration or reducing or preventing hepatocyte death. They are further useful for treating osteoarthritis or rheumatoid arthritis, or CNS-related diseases.

Cu-mediated selective bromination of aniline derivatives and preliminary mechanism study

A simple and efficient bromination of aniline, aniline derivatives, and analogs have been developed. Forty three examples were given and the highest yield reached was 98%. Different substrates including substituted aniline, pyridin-amine, N-substituted aniline, N,N-disubstituted aniline, N-phenyl-amide, N-phenyl-sulfonamide, and nitrogen-containing heterocycles were all reactive and selectively generated desired bromo-products. The method can be applied to synthesize drug intermediate and quinoxaline derivatives.

Facile Chan-Lam coupling using ferrocene tethered N-heterocyclic carbene-copper complex anchored on graphene

Ferrocene tethered N-heterocyclic carbene-copper complex anchored on graphene ([GrFemImi]NHC@Cu complex) has been synthesized by covalent grafting of ferrocenyl ionic liquid in the matrix of graphene followed by metallation with copper (I) iodide. The [GrFemImi]NHC@Cu complex has been characterized by fourier transform infrared (FT-IR), fourier transform Raman (FT-Raman), CP-MAS 13C NMR spectroscopy, transmission electron microscopy (TEM), thermogravimetric analysis (TGA), energy dispersive X-ray (EDX) analysis, X-ray photoelectron spectroscopy (XPS), Brunauer–Emmett–Teller (BET) surface area analysis and X-ray diffractometer (XRD) analysis. This novel complex served as a robust heterogeneous catalyst for the synthesis of bioactive N-aryl sulfonamides from variety of aryl boronic acids and sulfonyl azides in ethanol by Chan-Lam coupling. Recyclability experiments were executed successfully for six consecutive runs.

A focused fragment library targeting the antibiotic resistance enzyme - Oxacillinase-48: Synthesis, structural evaluation and inhibitor design

β-Lactam antibiotics are of utmost importance when treating bacterial infections in the medical community. However, currently their utility is threatened by the emergence and spread of β-lactam resistance. The most prevalent resistance mechanism to β-lactam antibiotics is expression of β-lactamase enzymes. One way to overcome resistance caused by β-lactamases, is the development of β-lactamase inhibitors and today several β-lactamase inhibitors e.g. avibactam, are approved in the clinic. Our focus is the oxacillinase-48 (OXA-48), an enzyme reported to spread rapidly across the world and commonly identified in Escherichia coli and Klebsiella pneumoniae. To guide inhibitor design, we used diversely substituted 3-aryl and 3-heteroaryl benzoic acids to probe the active site of OXA-48 for useful enzyme-inhibitor interactions. In the presented study, a focused fragment library containing 49 3-substituted benzoic acid derivatives were synthesised and biochemically characterized. Based on crystallographic data from 33 fragment-enzyme complexes, the fragments could be classified into R1 or R2 binders by their overall binding conformation in relation to the binding of the R1 and R2 side groups of imipenem. Moreover, binding interactions attractive for future inhibitor design were found and their usefulness explored by the rational design and evaluation of merged inhibitors from orthogonally binding fragments. The best inhibitors among the resulting 3,5-disubstituted benzoic acids showed inhibitory potential in the low micromolar range (IC50 = 2.9 μM). For these inhibitors, the complex X-ray structures revealed non-covalent binding to Arg250, Arg214 and Tyr211 in the active site and the interactions observed with the mono-substituted fragments were also identified in the merged structures.

Soft-Hard Acid/Base-Controlled, Oxidative, N-Selective Arylation of Sulfonanilides via a Nitrenium Ion

In iodine(III)-catalyzed, dehydrogenative arylations of sulfonanilides, the functionalization of C-C bonds is preferred over the functionalization of C-N bonds. Herein, an unprecedented N-selective arylation of sulfonanilides using soft-hard acid-base (SHAB) control by a nitrenium ion over a carbenium ion is reported. Treatment of sulfonanilides with iodine(III) led to the formation of nitrenium ions (soft), which preferentially react with biphenyls (soft) over bimesityl (hard) to generate C-N bonds. The iodine(III) was generated in situ by using PhI and mCPBA at room temperature.

Synthesis of CF3CH2-Containing Indolines by Transition-Metal-Free Aryltrifluoromethylation of Unactivated Alkenes

With an unactivated double bond as the radical acceptor, allyl amines underwent a metal-free trifluoromethylation/cyclization cascade with CF3SO2Na (Langlois' reagent), affording CF3CH2-containing indolines and tetrahydroisoquinolines, whose practical syntheses are significant challenges. This protocol features mild conditions, low cost, and a broad substrate scope.

Synthetic method of CF3-containing indoline and 1,2,3,4-tetrahydroisoquinoline

The invention discloses a synthetic method of CF3-containing indoline and 1,2,3,4-tetrahydroisoquinoline and relates to the technical field of compound synthesis. The synthetic method herein is basedon metal-free trifluoromethylation/cyclization free radical cascade reaction using a nonactive olefin dual-bond as a free radical receptor; the reaction aforementioned helps synthesize, in one step, CF3-containing indoline and 1,2,3,4-tetrahydroisoquinoline. The synthetic method herein has the significant advantages of mild conditions, good operational simplicity, low cost, wide substrate range, good exo selectivity and the like.