32857-49-1

Basic information

• Product Name: Benzenesulfonamide, N-(4-bromophenyl)-N,4-dimethyl-
• CAS NO: 32857-49-1
• Molecular Formula: C14H14BrNO2S
• Molecular Weight: 340.241
• Mol File: 32857-49-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, N-(4-bromophenyl)-N,4-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, N-(4-bromophenyl)-N,4-dimethyl-(32857-49-1)
• EPA Substance Registry System: Benzenesulfonamide, N-(4-bromophenyl)-N,4-dimethyl-(32857-49-1)

Safety Data

• Hazardous Substances Data: 32857-49-1(Hazardous Substances Data)

Upstream product

• 586-77-6 4-bromo-N,N-dimethylaniline 
• 98-59-9 p-toluenesulfonyl chloride 
• 6911-87-1 4-bromo-N-methylaniline 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 106-40-1 4-bromo-aniline 
• 32857-48-0 N-(4-bromophenyl)-4-methylbenzenesulfonamide 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 639520-70-0 4-(N-tert-butyloxycarbonyl-N-methylamino)phenyl bromide 
• 53973-85-6 N-Methyl-2-(4-methylphenylsulfonyl)benzolamin 
• 95793-81-0 5-Methyl-2-benzoesaeure 
• 16879-68-8 4-benzoesaeure 

Relevant articles and documents

Synthesis of sulfonamides: Via copper-catalyzed oxidative C-N bond cleavage of tertiary amines

A copper-catalyzed coupling reaction of sulfonyl chlorides with tertiary amines via the oxidative C-N bond cleavage of tertiary amines was developed. Sulfonamides were synthesized using this strategy in moderate to good yields. The reaction was applicable to various tertiary amines, as well as sulfonyl chlorides.

Gold-catalysed oxyarylation of styrenes and mono- and gem-disubstituted olefins facilitated by an iodine(III) oxidant

1-Hydroxy-1,2-benziodoxol-3(1H)-one (IBA) is an efficient terminal oxidant for gold-catalysed, three-component oxyarylation reactions. The use of this iodine(III) reagent expands the scope of oxyarylation to include styrenes and gem-disubstituted olefins, substrates that are incompatible with the previously reported Selectfluor-based methodology. Diverse arylsilane coupling partners can be employed, and in benzotrifluoride, homocoupling is substantially reduced. In addition, the IBA-derived co-products can be recovered and recycled. The I's have it: The unprecedented use of an iodine(III) reagent as the terminal oxidant for gold-catalysed oxyarylation allows the substrate scope to be significantly expanded; in addition to monosubstituted olefins, styrenes and gem-disubstituted olefins are well tolerated (see scheme). With benzotrifluoride as solvent, unproductive homodimerisation of the arylsilane coupling partner is effectively suppressed. Copyright

Possibilities and Limits of the Carbanionically Induced Sulfonamide-Aminosulfone Rearrangement

When transfering the title reaction to the 2- and 1-naphthyltoluenesulfonamides 5 and 10, the -shift of the arylsulfonyl group proceeds into the 3- and 2-position (to give 9 and 12, respectively), which is in full compliance with optimal conjugative and steric conditions for the relevant intermediates 8 and 11.Attemps to initiate comparable -rearrangements through the o-lithiated biphenyl derivative 17 and the p-lithiated N-phenyltoluenesulfonamide 23 led again, after extended transmetalation cascades, to the conventional -rearrangement products 22 and 32, respectively.In attempting to cause in the o-tolylbenzenesulfonamide 49 an anionically induced -sulfonyl shift into the benzyl position, two fragments of the starting molecule combined to give the novel heteropolycycle 51.Finally, it could be shown that contrary to the literature, the sulfonamides 46 and 57 rearrange also photolytically to the o-aminosulfones 45 and 58.