90264-13-4

Upstream product

• 37051-70-0 4-methyl-N-(4-oxocyclohexa-2,5-dien-1-ylidene)benzenesulfonamide 
• 1146-43-6 N-(4-hydroxyphenyl)-4-methylbenzenesulfonamide 
• 609-21-2 2,6-dibromo-4-aminophenol 
• 98-59-9 p-toluenesulfonyl chloride 
• 107590-46-5 N-(3-bromo-4-oxocyclohexa-2,5-dien-1-ylidene)-4-methylbenzenesulfonamide 
• 107590-50-1 2-bromo-4-(p-tolylsulfonylamino)phenol 

Downstream Products

• 107590-48-7 2,6-dibromo-4-(p-tolylimino)-1,4-benzoquinone 
• 100073-66-3 N-p-methylbenzenesulfonyl-2,6-dibromo-1,4-benzoquinone imine 

Relevant academic research and scientific papers

Synthesis of Polyhalogenated 2-Cyclohexane-1,4-dione Derivatives Containing Hydrogen at the sp3-Carbon Atoms from N-Arylsulfonyl-p-quinonimines and N,N'-Bis(arylsulfonyl)-p-quinonediimines

Chlorination and bromination of N-arylsulfonyl-1,4-benzo(naphtho)quinonimines, N,N'-bis(arylsulfonyl)-1,4-benzoquinonediimines, N-arylsulfonyl-4-aminophenols, and N-arylsulfonyl-4-aminonaphthols gave a number of stable polyhalogenated structures containing hydrogen at the sp3-hybridized carbon atoms. The chlorination and bromination schemes of N-arylsulfonyl-p-quinonimines are discussed.

HYDROBROMINATION OF N-ARYLSULFONYL-1,4-BENZO(NAPHTHO)QUINONE MONO- AND DIIMINES

The hydrobromination of N-arylsulfonyl-1,4-benzo(naphtho)quinone monoimines led to 2-bromo-4-arenesulfonamidophenols (or the corresponding 1-naphthols) and 2,6-dibromo-4-arenesulfonamidophenols.Their oxidation gave N-arylsulfonyl-2-bromo-1,4-benzo(naphtho

BROMINATION OF 4-ARENESULFONAMIDOPHENOLS (OR 1-NAPHTHOLS) AND N-ARYLSULFONYL-1,4-BENZO(NAPHTHO)QUINON-4-IMINES

2,3,6-Tribromo-N-phenylsulfonyl-1,4-benzoquinon-4-imines are formed on bromination of 4-arenesulfonamidophenols and N-aryl-sulfonyl-1,4-benzoquinon-4-imines but 2-bromo-N-arylsulfonyl-1,4-naphthoquinon-4-imines are formed from 4-arenesulfonamido-1-naphthols and N-arylsulfonyl-1,4-naphthoquinon-4-imines.

REACTION OF HYDROGEN BROMIDE WITH N-(p-TOLYL)- AND N-(p-TOLYLSULFONYL)-1,4-BENZOQUINONE MONOIMINES

In the reaction of hydrogen bromide with N-(p-tolyl)-1,4-benzoquinone monoimines bromination of the p-tolyl fragment takes place as well as nucleophilic addition.Bromination is fully suppressed by the addition of resorcinol to the reaction mass.In the case of N-(p-tolylsulfonyl)-1,4-benzoquinone monoimine the products from the entry of two bromine atoms at the ortho position to the oxygen atom are formed sucessively.