88046-97-3

Basic information

• Product Name: Benzenesulfenamide, N-(4-cyanophenyl)-
• CAS NO: 88046-97-3
• Molecular Formula: C13H10N2S
• Molecular Weight: 226.302
• Mol File: 88046-97-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzenesulfenamide, N-(4-cyanophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfenamide, N-(4-cyanophenyl)-(88046-97-3)
• EPA Substance Registry System: Benzenesulfenamide, N-(4-cyanophenyl)-(88046-97-3)

Safety Data

• Hazardous Substances Data: 88046-97-3(Hazardous Substances Data)

Upstream product

• 103375-36-6 C₁₆H₁₆N₂S 
• 108-98-5 thiophenol 
• 931-59-9 benzenesulfenyl chloride 
• 873-74-5 4-Aminobenzonitrile 

Downstream Products

• 67723-13-1 N-(4-cyanophenyl)-S-phenyl sulfonamide 
• 882-33-7 diphenyldisulfane 
• 122045-07-2 4,4'-(diazene-1,2-diyl)dibenzonitrile 

Relevant articles and documents

LDA-promoted decomposition of benzenesulfenamides. A route to aminyl radicals by dioxygen oxidation of lithium amides

The LDA-promoted decomposition of N-monosubstituted sulfenamides 1a-d occurs through the formation of thioaminyl anions, which undergo oxidation either at sulfur, with formation of sulfonamides, or at nitrogen, with formation of thioaminyl radicals, depending on the nature of the 4'-substituent. The reaction of N,N-disubstituted sulfenamides 1e-h proceeds through the intermediacy of a lithium complex capable of generating aminyl radicals via sulfenyl group transfer to the di-iso-propylamido anion and subsequent aerial oxidation of the resulting lithium amides 3e-h.

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.