38557-76-5

Basic information

• Product Name: N-hydroxy-4-methyl-N-phenylbenzenesulfonamide
• CAS NO: 38557-76-5
• Molecular Formula: C₁₃H₁₃NO₃S
• Molecular Weight: 263.3122
• Mol File: 38557-76-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 436.5°C at 760 mmHg
• Flash Point: 217.8°C
• Density: 1.354g/cm³
• Vapor Pressure: 2.16E-08mmHg at 25°C
• Refractive Index: 1.643
• CAS DataBase Reference: N-hydroxy-4-methyl-N-phenylbenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-hydroxy-4-methyl-N-phenylbenzenesulfonamide(38557-76-5)
• EPA Substance Registry System: N-hydroxy-4-methyl-N-phenylbenzenesulfonamide(38557-76-5)

Safety Data

• Hazardous Substances Data: 38557-76-5(Hazardous Substances Data)

Upstream product

• 536-57-2 p-toluene sulfinic acid 
• 100-65-2 N-Phenylhydroxylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 98-95-3 nitrobenzene 
• 586-96-9 Nitrosobenzene 

Downstream Products

• 536-57-2 p-toluene sulfinic acid 
• 586-96-9 Nitrosobenzene 
• 73539-06-7 trimethyltin N-phenyl-N-tosylhydroxylamine 
• 68-34-8 phenyl toluenesulfonamide 
• 959085-01-9 2-[(4-tolylsulfonyl)amino]phenyl methanesulfonate 
• 149210-39-9 diphenyltin(IV) bis(N-p-toluenesulfonyl-N-phenylhydroxylaminate) 
• 149210-37-7 (C₄H₉)2Sn(ON(C₆H₅)SO₂C₆H₄CH₃)2 

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.

Flow cell electrosynthesis of phenylhydroxylamines. In situ reaction with arenesulfonyl chlorides. A convenient route to arenesulfinic acids synthesis.

First, electrosyntheses of phenylhydroxylamines in a flow cell fitted with porous cathode and two counter-electrodes are described.Good yields are attained when electrolyses are performed in buffered aqueous organic or aqueous media.Reaction between p-toluenesulfonyl chloride and N-(3-chloro-4-methylphenyl)hydroxylamine, at the outlet of the cell, leads to a N-sulfonylated phenylhydroxylamine (N-addition); hydrolysis of this latter occurs in aqueous basic media to give the corresponding nitrosobenzene and sodium p-toluenesulfinate.As a result, some arenesulfinic acids have been directly obtained after reaction of arenesulfonyl chloride with sodium salt of 3-hydroxylaminobenzoate and 3-hydroxylaminobenzenesulfonate in aqueous phosphate buffer (pH 7).Next, an examination of the reaction of p-toluenesulfonyl chloride with phenylhydroxylamine in organic solvent, in the presence of triethylamine or of sodium carbonate, shows the importance of experimental conditions to control N-addition or O-addition.Addition of some arenesulfonyl chlorides to phenylhydroxylamine, in ether or dichloromethane containing sodium carbonate, gives only the N-sulfonylated phenylhydroxylamines.These compounds lead to nitrosobenzene and arenesulfinate anions in aqueous basic media.Aliphatic or aromatic sulfinic acids can be prepared in this way.