7454-58-2

Usage

Uses

Used in Dye Industry:
4-BROMO-4'-METHYLBENZENESULFONANILIDE is used as a dye intermediate for the production of various dyes. Its chemical properties allow it to contribute to the color and stability of the dyes, making it an essential component in the dye manufacturing process.
Used in Pharmaceutical Industry:
4-BROMO-4'-METHYLBENZENESULFONANILIDE is utilized as an intermediate in the synthesis of various pharmaceuticals. Its role in inhibiting the enzyme carbonic anhydrase makes it a valuable component in the development of drugs for the treatment of glaucoma and other conditions involving abnormal fluid retention in the eye.
Used as a Chemical Intermediate:
In addition to its industrial and pharmaceutical applications, 4-BROMO-4'-METHYLBENZENESULFONANILIDE is also used as a chemical intermediate for the synthesis of other organic compounds. Its unique chemical structure enables it to be a key component in the creation of a wide range of organic molecules, further expanding its utility in the chemical industry.

InChI:InChI=1/C13H12BrNO2S/c1-10-2-6-12(7-3-10)15-18(16,17)13-8-4-11(14)5-9-13/h2-9,15H,1H3

Upstream product

• 941-55-9 4-toluenesulfonyl azide 
• 5467-74-3 4-Bromophenylboronic acid 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 624-31-7 4-tolyl iodide 
• 701-34-8 4-bromo-benzenesulfonic acid amide 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 106-40-1 4-bromo-aniline 
• 98-58-8 4-bromobenzenesulfonyl chloride 
• 99-99-0 1-methyl-4-nitrobenzene 
• 34176-08-4 sodium 4-bromobenzenesulfinate 
• 106-49-0 p-toluidine 

Downstream Products

• 680588-88-9 2-[(4-bromo-benzenesulfonyl)-p-tolyl-amino]-N,N-diethyl-acetamide 

Relevant academic research and scientific papers

Nitrosoarenes as Nitrogen Source for Generation of Sulfonamides with the Insertion of Sulfur Dioxide under Metal-Free Conditions?

A metal-free reaction of nitrosoarenes, aryldiazonium tetrafluoroborates, and sulfur dioxide under mild conditions is developed, giving rise to sulfonamides in moderate to good yields. This transformation proceeds efficiently at room temperature in the presence of cyclohexa-1,4-diene with a broad reaction scope. Good functional group compatibility is observed, including cyano, halo, and ester. A plausible mechanism involving a radical process with the insertion of sulfur dioxide is proposed, and cyclohexa-1,4-diene serves as the reductant during the transformation.

Ligand-Enabled Gold-Catalyzed C(sp2)-N Cross-Coupling Reactions of Aryl Iodides with Amines

The first example of ancillary (P,N)-ligand-enabled gold-catalyzed C-N cross-coupling reactions of aryl iodides with amines is reported. The high generality of the reaction in de novo synthesis, late-stage modifications, and cascade processes to access functionalized indolinones and carbazoles underscores the synthetic potential of the presented strategy. Monitoring the reaction with ESI-HRMS and NMR provided strong evidence for the in situ formation of putative high valent Au(III) intermediates.

Copper-catalyzed redox coupling of nitroarenes with sodium sulfinates

A simple copper-catalyzed redox coupling of sodium sulfinates and nitroarenes is described. In this process, abundant and stable nitroarenes serve as both the nitrogen sources and oxidants, and sodium sulfinates act as both reactants and reductants. A variety of aromatic sulfonamides were obtained in moderate to good yields with broad substrate scope. No external additive is employed for this kind of transformation.

Tert -Butyl nitrite mediated nitrogen transfer reactions: Synthesis of benzotriazoles and azides at room temperature

A conversion of o-phenylenediamines into benzotriazoles was achieved at room temperature using tert-butyl nitrite. The optimized conditions are also well suited for the transformation of sulfonyl and acyl hydrazines into corresponding azides. This protocol does not require any catalyst or acidic medium. The desired products were obtained in excellent yields in a short span of time.

N-Glycine-sulfonamides as potent dual orexin 1/orexin 2 receptor antagonists

A series of dual OX1R/OX2R orexin antagonists was prepared based on a N-glycine-sulfonamide core. SAR studies of a screening hit led to compounds with low nanomolar affinity for both receptors and good oral bioavailability. One of these compounds, 47, has demonstrated in vivo activity in rats following oral administration.

Effect of para substitution on dissociation of N-phenylbenzenesulfonamides

The reaction of substituted anilines and benzenesulfonyl chlorides has been used to prepare 49 substituted N-phenylbenzenesulfonamides of general formula 4-X-C6H4SO2NHC6H4-Y- 4′. Their purity was checked by elemental analysis. The substituents X and Y include H, CH3, CH3O, Cl, Br, CN, and NO2. The dissociation constants of all compounds were determined by potentiometric titration in methanol, acetonitrile, N,N-dimethylformamide, and pyridine. The obtained dissociation constants, pKHA, were correlated with various sets of substituent constants. It was found that the effects of substituents X and Y on the dissociation are best described by using the Hammett equation with σp constants and the Yukawa-Tsuno equation with σp- and σp constants, respectively. This result confirms the direct conjugation of Y substituent with the reaction centre. The explained variability using the additive model was above 96% in all the solvents used. The data also provided information about the transmission effect of the SO2 group. The average dissociation constants were further processed by the latent variables methods, principal components and conjugated deviations analyses.