2654-68-4

Basic information

• Product Name: Benzenesulfonamide, N,N'-1,4-phenylenebis[4-chloro-
• CAS NO: 2654-68-4
• Molecular Formula: C18H14Cl2N2O4S2
• Molecular Weight: 457.358
• Mol File: 2654-68-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, N,N'-1,4-phenylenebis[4-chloro-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, N,N'-1,4-phenylenebis[4-chloro-(2654-68-4)
• EPA Substance Registry System: Benzenesulfonamide, N,N'-1,4-phenylenebis[4-chloro-(2654-68-4)

Safety Data

• Hazardous Substances Data: 2654-68-4(Hazardous Substances Data)

Upstream product

• 100-03-8 4-chlorobenzenesulfinic acid 
• 100-01-6 4-nitro-aniline 
• 173257-70-0 C₁₈H₁₂Br₂Cl₂N₂O₄S₂ 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 106-50-3 1,4-phenylenediamine 
• 2654-77-5 N,N′-(cyclohexa-2,5-diene-1,4-diylidene)bis-(4-chlorobenzenesulfonamide) 
• 624-18-0 benzene-1,4-diamine hydrochloride 

Downstream Products

• 173257-72-2 N,N'-(2,5-dibromo-1,4-phenylene)bis(4-chlorobenzenesulfonamide) 
• 173097-13-7 C₁₈H₈Cl₈N₂O₄S₂ 
• 173097-12-6 2,3,5,5,6,6-Hexachloro-1,4-di-p-tolylsulfonylimino-2-cyclohexene 
• 159983-63-8 C₁₈H₈Cl₆N₂O₄S₂ 
• 76165-53-2 2,3,5,6-tetrachloro-N,N'-ditosyl-p-phenylenediamine 
• 76165-36-1 N,N'-bis-p-toluenesulfonyl-2,3,5,6-tetrachloro-1,4-benzoquinone diimine 
• 159983-62-7 C₁₈H₁₀Cl₆N₂O₄S₂ 
• 2654-77-5 N,N′-(cyclohexa-2,5-diene-1,4-diylidene)bis-(4-chlorobenzenesulfonamide) 
• 173257-70-0 C₁₈H₁₂Br₂Cl₂N₂O₄S₂ 

Relevant articles and documents

Paired electrochemical conversion of nitroarenes to sulfonamides, diarylsulfones and bis(arylsulfonyl)aminophenols

A paired electrochemical method using nitrobenzene (NB) derivatives and arylsulfinic acids (ASAs) as starting materials was developed for the synthesis of some new sulfonamides, diarylsulfones and bis(arylsulfonyl)aminophenols. The synthetic strategy was designed using the data provided by electrochemical studies involving cyclic voltammetry on NB oxidation in the absence and presence of ASAs. The reactions have been successfully performed in an undivided cell, at carbon rod electrodes, in aqueous solutions, by constant current electrolysis at room temperature. This strategy does not require catalysts, toxic solvents and challenging workups. It is also applicable for a wide range of nitroarenes.

Some reactions of new semiquinoid compounds derived from N-arylsulfonyl-p-quinonimines

Polyhalogenated semiquinoid compounds on the basis of N-arylsulfonyl-p-quinonimines react with reducing agents (zinc or sodium dithionite in acetic acid) with elimination of one or two hydrogen halide molecules, depending on the number of hydrogens at the sp3-hybridized carbon atoms, to give the corresponding benzoid structures. Dehydrohalogenation of the title compounds in chloroform in the presence of triethylamine leads to formation of quinonimines. N,N′-Bis(arylsulfonyl)-p-quinonediimine derivatives do not undergo dehydrohalogenation. Reactions with dialkyl hydrogen phosphites result mostly in 1,2-addition and formation of phosphorylated products; the reaction is likely to involve intermediate dehydrohalogenation to the corresponding quinonimines which can be isolated in the pure state.

CHLORINATION OF N,N'-BISARYLSULFONYL-1,4-PHENYLENEDIAMINES AND N,N'-BISARYLSULFONYL-1,4-BENZOQUINONE DIIMINES

The chlorination of N,N'-bisarylsulfonyl-1,4-phenylenediamines leads to 1,4-bisarylsulfonylimino-2,3,5,5,6,6-hexachloro-2-cyclohexenes.Together with the chlorination products chloranil and/or 2,3,5,5,6,6-hexachloro-1,2-cyclohexene-1,4-dione were isolated as a result of the competing hydrolysis process.