88047-06-7

Basic information

• Product Name: Benzenesulfenamide, N-phenyl-N-(phenylthio)-
• CAS NO: 88047-06-7
• Molecular Formula: C18H15NS2
• Molecular Weight: 309.456
• Mol File: 88047-06-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzenesulfenamide, N-phenyl-N-(phenylthio)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfenamide, N-phenyl-N-(phenylthio)-(88047-06-7)
• EPA Substance Registry System: Benzenesulfenamide, N-phenyl-N-(phenylthio)-(88047-06-7)

Safety Data

• Hazardous Substances Data: 88047-06-7(Hazardous Substances Data)

Upstream product

• 14933-91-6 N-phenyl-benzenesulphenamide 
• 63235-31-4 benzenesulfenic acid p-anisidide 
• 931-59-9 benzenesulfenyl chloride 
• 62-53-3 aniline 

Downstream Products

• 14933-91-6 N-phenyl-benzenesulphenamide 
• 82993-63-3 N-phenyl-N'-phenylthio-p-benzoquinone di-imine 
• 106-47-8 4-chloro-aniline 
• 882-33-7 diphenyldisulfane 

Relevant articles and documents

Benzenesulphenanilidyl Radicals. Part 3. Reactions of 4'-Substituted Benzenesulphenanilides with t-Butoxyl Radicals

Decomposition products of the 4'-substituted benzenesulphenanilidyl radicals (2a, b, d, and e), generated from the corresponding benzenesulphenanilides (1) with t-butoxyl radicals, have been investigated in benzene, acetonitrile, and acetone.Results indicate that the decomposition modes exhibited by these radicals are not essentially influenced by variation of the solvent polarity; comparison of the findings with present and previous results from oxidation of (1) with lead dioxide show that the chemical reactivity trend displaced by the thioaminyls (2) can be greatlyinfluenced both by the reaction medium and the 4'-substituent.Evidence is presented that the benzenesulphenanilides (1b) and (1e) react in acetone in the presence of di-t-butyl hyponitrite to give products ascribable to homolytic substitution at the sulphenanilide sulphur by acetonyl radicals.

Benzenesulphenanilidyl Radicals. Part 2. Substituent and Solvent Effects on the Reactivity of 4'-Substituted Benzenesulphenanilidyl Radicals Produced by Oxidation with Lead Dioxide of the Corresponding Benzenesulphenanilides

Oxidation of benzenesulphenanilide (1d) with lead dioxide in benzene affords the p-benzoquinone diimine (5d) together with minor amounts of N,N-bis(phenylthio)aniline (4d) and diphenyl disulphide (7a).The formation of the products is explained in terms of p-C-N coupling of the benzenesulphenanilidyl radicals (2d) and subsequent fragmentation of the resulting dimer.A similar trend is observed in the oxidation of 4'-chloro- and 4'-bromo-benzenesulphenanilides (1e) and (1f), whereas 4'-nitrobenzenesulphenanilide (1g) leads to the o-phenylenediamine (12g), arising from o-C-N coupling of the sulphenanilidyl radical (2g).The oxidation of the sulphenanilides (1e) and (1f) in acetonitrile produces the phenazines (3e) and (3f) and the disulphide (7a), whereas the anilide (1g) and 4'-cyanobenzenesulphenanilide (1h) give azobenzenes (11g) and (11h) and the disulphide (7a); these results are discussed in terms of a possible mechanism involving oxidation of the N-N dimers (14e-h) which are in rapid equilibrium with the corresponding sulphenanilidyl radicals (2e-h).Evidence is also presented that the oxidation of 2-nitrobenzenesulphenanilides leads to products ascribable to intermediate 2-nitrobenzenesulphenanilidyl radicals, in contrast with a previous claim.