98192-14-4

Basic information

• Product Name: 2-Bromo-N-methylbenzenesulphonamide
• Synonyms: 2-Bromo-N-methylbenzenesulphonamide;N-Methyl 2-bromobenzenesulphonamide;2-Bromo-N-methylbenzenesulphonamide 98%;2-Bromo-N-methylbenzenesulfonamide;N-Methyl 2-bromobenzenesulfonamide;2-Bromo-N-methylbenzenesulphonamide98%
• CAS NO: 98192-14-4
• Molecular Formula: C₇H₈BrNO₂S
• Molecular Weight: 250.11292
• Product Categories: blocks;Bromides;Sulfonamides
• Mol File: 98192-14-4.mol

Chemical Properties

• Boiling Point: 341.9 °C at 760mmHg
• Flash Point: 160.6 °C
• Appearance: /
• Density: 1.601 g/cm³
• Vapor Pressure: 7.8E-05mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-Bromo-N-methylbenzenesulphonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-N-methylbenzenesulphonamide(98192-14-4)
• EPA Substance Registry System: 2-Bromo-N-methylbenzenesulphonamide(98192-14-4)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 98192-14-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-N-methylbenzenesulphonamide is used as an intermediate for the production of various pharmaceutical products due to its antimicrobial properties and its role in the synthesis of sulfonamides and related compounds.
Used in Agrochemical Industry:
2-Bromo-N-methylbenzenesulphonamide is used as an active ingredient in the development of agrochemicals, particularly as an antibacterial and antifungal agent, to protect crops from microbial infections and ensure a healthy yield.
Used in Organic Synthesis:
2-Bromo-N-methylbenzenesulphonamide is used as a reagent in organic synthesis, particularly in the preparation of sulfonamides and related compounds, contributing to the advancement of chemical research and the development of new chemical entities.

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

Upstream product

• 80-43-3 bis(1-methyl-1-phenylethyl)peroxide 
• 92748-09-9 2-bromobenzene-1-sulfonamide 
• 5183-78-8 methyl(phenylsulfonyl)amide 
• 2905-25-1 o-bromobenzenesulfonyl chloride 
• 593-51-1 methylamine hydrochloride 
• 576-92-1 bromobenzene-2-sulfonic acid 
• 88-21-1 2-amino-1-benzenesulfonic acid 
• 7154-66-7 2-bromobenzoic acid chloride 
• 74-89-5 methylamine 

Downstream Products

• 1438432-27-9 N-allyl-2-bromo-N-methylbenzenesulfonamide 
• 1242459-15-9 4-benzylidene-2-methyl-3,4-dihydro-2H-benzo[e][1,2]thiazine-1,1-dioxide 
• 18963-38-7 N-methyl-2-(phenylethynyl)benzenesulfonamide 

Relevant articles and documents

Copper-catalyzed oxidative methylation of sulfonamides by dicumyl peroxide

A novel and facile copper-catalyzed methylation of sulfonamides was herein demonstrated. The practical transformation took place readily under the oxidative conditions, and N-methyl amides (23 examples) were successfully furnished in high efficiency (up to 90% yields). Dicumyl peroxide was considered to act not only as the oxidant in the system, but also methyl donor for the methylation protocol.

Synthesis of novel isoflavone/benzo-δ-sultam hybrids as potential anti-inflammatory drugs

A small series of novel isoflavone/benzo-δ-sultam hybrids was synthesised and evaluated as potential anti-inflammatory and neuroprotective drugs in LPS-activated BV2 microglia. The benzo-δ-sultam core was constructed in a two-step reaction by coupling 2-halobenzenesulfonamide derivatives with terminal alkynes, followed by a 6-endo-dig cyclisation. The synthesised compounds, including precursors and hybrids, were tested for their ability to inhibit NO and TNF-α production in LPS-stimulated BV2 microglial cells, and the results are promising. The most potent hybrid reduces the NO production to 41%, and the TNF-α to 34% at 20 μM final concentration in the well.

Structurally Diverse Synthesis of Five-, Six-, and Seven-Membered Benzosultams through Electrochemical Cyclization

We have developed a metal- and oxidant-free approach to structurally diverse synthesis of benzosultams from aryl sulfonamides through an electrochemical cyclization. Upon variation of the ortho substituent on aryl sulfonamides, five-, six-, and seven-memb

Cobalt-Catalyzed 1,4-Aryl Migration/Desulfonylation Cascade: Synthesis of α-Aryl Amides

A cobalt-catalyzed 1,4-aryl migration/disulfonylation cascade applied to α-bromo N-sulfonyl amides was developed. The reaction was highly chemoselective, allowing the preparation of α-aryl amides possessing a variety of functional groups. The method was used as the key step to synthesize an alkaloid, (±)-deoxyeseroline. Mechanistic investigations suggest a radical process.

Nickel-catalyzed regioselective C-H halogenation of electron-deficient arenes

A straightforward Ni(ii)-catalyzed general strategy was developed for the ortho-halogenation of electron-deficient arenes with easily available halogenating reagents N-halosuccinimides (NXS; X = Br, Cl and I). The transformation was highly regioselective and a wide substrate scope and functional group tolerance were observed. This discovery could be of great significance for the selective halogenation of amides, benzoic esters and other substances with guiding groups. Mechanistic investigations were also described.

Dynamic Covalent Chemistry within Biphenyl Scaffolds: Reversible Covalent Bonding, Control of Selectivity, and Chirality Sensing with a Single System

Axial chirality is a prevalent and important phenomenon in chemistry. Herein we report a combination of dynamic covalent chemistry and axial chirality for the development of a versatile platform for the binding and chirality sensing of multiple classes of mononucleophiles. An equilibrium between an open aldehyde and its cyclic hemiaminal within biphenyl derivatives enabled the dynamic incorporation of a broad range of alcohols, thiols, primary amines, and secondary amines with high efficiency. Selectivity toward different classes of nucleophiles was also achieved by regulating the distinct reactivity of the system with external stimuli. Through induced helicity as a result of central-to-axial chirality transfer, the handedness and ee values of chiral monoalcohol and monoamine analytes were reported by circular dichroism. The strategies introduced herein should find application in many contexts, including assembly, sensing, and labeling.

Copper-Catalyzed Arylsulfonylation and Cyclizative Carbonation of N-(Arylsulfonyl)acrylamides Involving Desulfonative Arrangement toward Sulfonated Oxindoles

Sulfonated oxindoles are accessed by a Cu(OAc)2-catalyzed three-component reaction of N-(arylsulfonyl)acrylamides, DABSO, and aryldiazonium tetrafluoroborates. This transformation is triggered by the formation of arylsulfonyl radicals in situ from the reaction of aryldiazonium tetrafluoroborates and DABSO. Afterward, the sequential radical addition, radical cyclization, and desulfonylative 1,4-aryl migration take place to provide the final product by the formation of four new bonds in one pot. This procedure shows good functional group tolerance.

Regio- and Stereoselective Synthesis of Benzo-δ-sultams by Palladium-Catalyzed Hydrocarbonation of Alkynes

An efficient method for the synthesis of benzo-δ-sultams [(4Z)-4-benzylidene-2-(arylmethyl)-3,4-dihydro-2H-1,2-benzothiazine 1,1-dioxides] via palladium(0)-catalyzed hydrocarbonation of alkynes is presented. This method allows regioselective access to a variety of substituted benzosultams in excellent yields under mild conditions. The stereochemistry of the exocyclic double bond of the benzosultam derivatives is confirmed by single-crystal X-ray diffraction.

Ligand free Pd catalyzed cyclization-influence of steric hindrance

Synthesis of sultams was performed using ligand free palladium catalyst following Heck cyclization. The diverse synthesized intermediates in this strategy includes halogenated sulfonyl chloride, alkyl/aryl sulfonamides, N-alkylation using halogenated alke

Lewis acid catalyzed cascade reaction of 3-(2-benzenesulfonamide)propargylic alcohols to spiro[indene-benzosultam]s

A highly efficient and convenient construction of the spiro[indene-benzosultam] skeleton from propargylic alcohols has been developed. The reaction proceeded in a Lewis acid catalyzed cascade process, including the trapping of allene carbocation with sulfonamide, electrophilic cyclization, and intramolecular Friedel-Crafts alkylation. In the presence of NIS or NBS, iodo/bromo-substituted spiro[indene-benzosultam]s could be prepared in excellent yields.