87995-68-4

Basic information

• Product Name: Benzenesulfonamide, N-(2-bromo-4-methylphenyl)-4-methyl-
• CAS NO: 87995-68-4
• Molecular Formula: C14H14BrNO2S
• Molecular Weight: 340.241
• Mol File: 87995-68-4.mol

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, N-(2-bromo-4-methylphenyl)-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, N-(2-bromo-4-methylphenyl)-4-methyl-(87995-68-4)
• EPA Substance Registry System: Benzenesulfonamide, N-(2-bromo-4-methylphenyl)-4-methyl-(87995-68-4)

Safety Data

• Hazardous Substances Data: 87995-68-4(Hazardous Substances Data)

Upstream product

• 599-86-0 4-methyl-N-(4-methylphenyl)benzenesulfonamide 
• 583-68-6 2-bromo-p-toluidine 
• 98-59-9 p-toluenesulfonyl chloride 
• 87995-69-5 N-(2-Brom-4-methylphenyl)-4-methyl-N-(4-methylphenylsulfonyl)benzamid 
• 594-19-4 tert.-butyl lithium 

Downstream Products

• 1170354-50-3 C₂₅H₂₄BrNO₄S 
• 1160847-21-1 1,6-dimethyl-9-(4-methylbenzenesulfonyl)-9H-carbazole 
• 1448756-44-2 5-methyl-2,3-diphenyl-1-tosyl-1H-indole 
• 1330574-17-8 ethyl 2-(5,6-dihydro-2-methyl-5-tosylphenanthridin-6-yl)acetate 
• 1587691-88-0 N-(2-bromo-4-methylphenyl)-4-methyl-N-(prop-2-ynyl)benzenesulfonamide 

Relevant articles and documents

Directing-group-assisted markovnikov-selective hydrothiolation of styrenes with thiols by photoredox/cobalt catalysis

In contrast with the well-developed radical thiol-ene reaction to access anti-Markovnikov-type products, the research on the catalytic Markovnikov-selective hydrothiolation of alkenes is very restricted. Because of the catalyst poisoning of metal catalysts by organosulfur compounds, limited examples of transition-metal-catalyzed thiol-ene reactions have been reported. However, in this work, a directing-group-assisted hydrothiolation of styrenes with thiols by photoredox/cobalt catalysis is found to proceed smoothly to afford Markovnikov-type sulfides with excellent regioselectivity.

Palladium-Catalyzed Regioselective Synthesis of 1-Hydroxycarbazoles Under Aerobic Conditions

A palladium-catalyzed aerobic C?H amidation of N-Ts-2-amino-3′-hydroxylbiaryls has been developed to afford a diverse range of 1-hydroxycarbazoles with high regioselectivity and efficiency. This protocol benefits from operational simplicity, robustness, a

Visible-Light-Driven Neutral Nitrogen Radical Mediated Intermolecular Styrene Difunctionalization

A neutral nitrogen radical-mediation strategy, wherein the existing N-H moiety of substrates serves as a neutral nitrogen radical precursor to enable room-temperature intermolecular radical difunctionalization of styrenes under photoredox catalysis, is reported. The reaction shows high functional group tolerance and substrate scope with respect to both components, giving the corresponding products with generally good yields. Preliminary control experiments and DFT calculations are performed to explain the reaction mechanism.

Self-induced stereoselective in situ trifluoromethylation: Preparation of spiro[indoline-3,3′-quinoline] via palladium-catalyzed cascade reaction

An efficient method to prepare 1′H-spiro[indoline-3,3′- quinoline]-2′,4′-diones and their trifluoromethylated products was developed via a palladium-catalyzed Sonogashira coupling/Wacker-type oxypalladation/cyclization cascade reaction. The amount of wate

Reductive Heck cyclization versus δ-carbon elimination/decarboxylation: synthesis of dihydroindole and indoles from Baylis-Hillman adducts

Modified Baylis-Hillman adducts having 2-bromoaniline moiety at the primary position underwent Pd-mediated reductive Heck type cyclization to produce dihydroindole derivatives. The same starting materials can also be used for the synthesis of indole deriv

Synthetic use of 1,1,2,2-tetraphenyldisilane for the preparation of biaryls through the intramolecular free radical ipso-substitution of N-(2-bromoaryl)arenesulfonamides

Treatment of various N-methyl-N-(2-bromoaryl)arenesulfonamides (1a-g, 1i, and 1m) with 1,1,2,2-tetraphenyldisilane and AIBN under heating conditions gave the corresponding biaryl products (2a-g, 2i, and 2m) in moderate yields through the intramolecular radical ipso-substitution. However, N-H free N-(2-bromoaryl)arenesulfonamides 1h and 2-bromoaryl arenesulfonate 1j did not give the corresponding biarys. 1,1,2,2-Tetraphenyldisilane is the most effective reagent for 1,5-ipso-substitution on the sulfonamides among typical radical reagents such as diphenylsilane, tributyltin hydride, tris(trimethylsilyl)silane, and 1,1,2,2-tetraphenyldisilane. Furthermore, 1,1,2,2-tetraphenyldisilane has the advantages of low toxicity, stability, and ease of preparation.

Carbanionically Induced -Migrations of ?- and Coordinatively Unsaturated Groups

According to a general reaction scheme, o-lithioaryl esters 4a,b, amides 13a,b 17b, and amidines 39b of non-enolizable carboxylic acids as well as a corresponding diphenylphosphinic amide 51b react under mild conditions to give the intensely coloured lithium derivatives of o-acylphenoles 6a,b and o-acylarenamines 15a,b, 18a, 41a, 52a, which are finally hydrolyzed to the neutral products 7a,b, 14a,b, 18b, 41b, 52b, respectively.The lithiated precursors of the rearrangement are mostly prepared by halogen/metal exchange reactions.In the case of N,N-di-p-tolylpivalamide 33 such a -rearrangement also could be induced by direct metalation of the educt.With N-methyl-N-phenylpivalamide (29), however, exclusive metalation of the N-methyl group occurs, followed by -migration of the pivaloyl group.Silyl groups, too, can undergo analogous -shifts, as was demonstrated by the rearrangement of the o-lithiated N-(trimethylsilyl)aniline 63b to the o-(trimethylsilyl)anilines 65a,b.When a benzoyl and sulfonyl group can compete for the -shifts, as in the N-tosylated benzamide 47b, only the benzoyl group migrates.However, the migration tendency of the trimethylsilyl group equals that of the benzoyl group as was shown with the N-silylated benzamide 66b.