141481-39-2

Basic information

• Product Name: Benzenesulfonamide, 4-methyl-N-(2,3,5,6-tetrachloro-4-hydroxyphenyl)-
• CAS NO: 141481-39-2
• Molecular Formula: C13H9Cl4NO3S
• Molecular Weight: 401.097
• Mol File: 141481-39-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, 4-methyl-N-(2,3,5,6-tetrachloro-4-hydroxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, 4-methyl-N-(2,3,5,6-tetrachloro-4-hydroxyphenyl)-(141481-39-2)
• EPA Substance Registry System: Benzenesulfonamide, 4-methyl-N-(2,3,5,6-tetrachloro-4-hydroxyphenyl)-(141481-39-2)

Safety Data

• Hazardous Substances Data: 141481-39-2(Hazardous Substances Data)

Upstream product

• 141481-37-0 2,3,5,5,6,6-hexachloro-4-<(p-tolylsulfonyl)imino>-2-cyclohexen-1-one 
• 141481-35-8 N-p-methylbenzenesulfonyl-2,3,5,6-tetrachloro-1,4-benzoquinone imine 
• 99323-78-1 C₁₃H₇Cl₄NOS 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 91358-28-0 C₁₂H₄Cl₄N₂O₃S 
• 7498-47-7 bis-(4-dimethylamino-phenyl)-hydroxyphosphine 
• 236739-30-3 2,3,5,6,6-pentachloro-4-tolylsulfonylimino-2-cyclohexenone 
• 1146-43-6 N-(4-hydroxyphenyl)-4-methylbenzenesulfonamide 

Downstream Products

• 141481-35-8 N-p-methylbenzenesulfonyl-2,3,5,6-tetrachloro-1,4-benzoquinone imine 

Relevant articles and documents

Reactions of 2,3,5,6-tetrachloro-N-arylsulfenyl-1,4-benzoquinonimines with arenesulfinic acids

Arenesulfinic acids react with 2,3,5,6-tetrachloro-N-arylsulfenyl-1,4-benzoquinonimines, following the 1,6-addition pattern. The reactions with excess arenesulfinic acid result in elimination of arenethiol and formation of 2,3,5,6-tetrachloro-4-arylsulfonylaminophenols. Oxidation of the latter yields 2,3,5,6-tetrachloro-N-arylsulfonyl-1,4-benzoquinonimines which are difficult to obtain by other methods.

Reaction of N-Arylsulfonyl-p-quinonimines and semiquinoid structures produced therefrom with Bis(p-dimethylaminophenyl)phosphinite

N-Arylsulfonyl-1,4-benzoquinonemonoimines react with bis(N-dimethylaminophenyl)phosphinite in keeping with the character and position of substituents in the quinoid ring along 1,4-, 6,1-, or 1,2-addition way; N-arylsulfonyl-1,4-naphthoquinonemonoimines react along 1,4-, 6,1-, 1,2-, or 6,3-addition. Semiquinoid polyhalostructures generated therefrom react similarly to the corresponding quinonimines possessing several chlorine substituents in the quinoid ring. N,N-Diarylsulfonyl-1,4-benzoquinonediimines with no substituents in the ring yield with bis(p-dimethylaminophenyl)phosphinite 1,4-addition products. Along a competing reaction quinonediimine is reduced to the corresponding phenylenediamine. With the tetrachloro substituted in the ring 1,4-benzoquinonediimine and the corresponding semiquinoid derivative only reduction is observed.

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.