13065-93-5

Usage

Uses

Used in Hair Dye Industry:
N-(4-chlorophenyl)-p-phenylenediamine is used as a key ingredient in hair dyes for its ability to produce a range of colors. It is valued for its effectiveness in coloring hair, although its use is regulated due to its potential to cause skin sensitization and other health issues.
Used in Rubber Industry:
In the rubber industry, N-(4-chlorophenyl)-p-phenylenediamine serves as an antioxidant, helping to prevent the degradation of rubber products over time. Its role in enhancing the durability and longevity of rubber goods is significant, yet it must be handled with care due to its toxic properties.
Given the potential health risks associated with N-(4-chlorophenyl)-p-phenylenediamine, including its classification as a possible human carcinogen by the International Agency for Research on Cancer, there are strict restrictions and regulations on its use and handling in various countries to mitigate exposure and protect public health.

Upstream product

• 7696-68-6 (4-chloro-phenyl)-(4-nitroso-phenyl)-amine 
• 4340-77-6 4-chloroazobenzene 
• 949-88-2 1-(4-chlorophenyl)-2-phenylhydrazine 
• 88047-08-9 N-(p-chlorophenyl)-N'-phenylthio-p-benzoquinone di-imine 
• 953-14-0 N,N'-bis(4-chlorophenyl)hydrazine 
• 7664-93-9 sulfuric acid 
• 932-98-9 1-chloro-4-nitroso-benzene 
• 64-19-7 acetic acid 
• 586-96-9 Nitrosobenzene 
• 7647-01-0 hydrogenchloride 
• 67-56-1 methanol 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 56795-80-3 N-(4-chloro-phenyl)-N-(4-nitroso-phenyl)-hydroxylamine 
• 7732-18-5 water 

Downstream Products

• 27174-02-3 4-Chloro-4'-isothiocyano-diphenylamin 
• 1221971-54-5 C₂₁H₁₆ClN₃O₄S 
• 1366234-27-6 C₁₆H₁₄ClN₅ 

Relevant academic research and scientific papers

ARYL-AND HETEROARYL-SUBSTITUTED BENZENE DERIVATIVES AS MODULATORS OF PI3-KINASE SIGNALLING PATHWAYS

The present disclosure relates to certain aryl- or heteroaryl-substituted benzene derivatives, pharmaceutical compositions containing them, and methods of using them, including methods for modulating autophagy or preventing, reversing, slowing or inhibiting the PI3K-AKT-MTOR pathway, and methods of treating diseases that are associated with autophagy or the PI3K-AKT-MTOR pathway.

Heavy-Atom Kinetic Isotope Effects and Mechanism of the Acid-Catalyzed o-Semidine and p-Semidine Rearrangements and Disproportionation of 4,4'-Dichlorohydrazobenzene

In acidic 60percent aqueous dioxane solution at 0 deg C, 4,4'-dichlorohydrazobenzene (18) undergoes concurrent disproportionation, to p-chloroaniline (19) and 4,4'-dichloroazobenzene (20), and o- (21) and p-semidine (22) rearrangement.In the p-semidine rearrangement one of the chlorine atoms of 18 is displaced, in essence, as Cl+.This requires participation of a second molecule of 18 in a redox reaction.The overall fate of 18, therefore, is to give 11percent o- and 12percent p-semidine rearrangement (along with 12percent of 20) and 60percent disproportionation, accounting for 95percent of the 18.Nitrogen and carbon kinetic isotope effects (KIE) have been determined for each of these reactions, using 18, 18, 18, and 18.Isotope ratios were obtained, measured on the trifluoroacetyl derivatives of 19, 21, and 22, with a combination of scintillation counting, whole-molecule-ion mass spectrometry (WMIMS), and isotope-ratio mass spectrometry (IRMS).Nitrogen KIE were obtained by WMIMS for two 15N atoms in disproportionation (1.0260) and p-semidine rearrangement (1.0282) and by IRMS for one (naturally abundant) 15N atom in disproportionation (1.0141) and o-(1.0155) and p-semide (1.0162) rearrangement. 13C (IRMS) and 14C KIE were measured for all reactions, but in no case was a KIE other than, effectively, unity obtained.These results show that o-semidine formation from 18 complies with exceptations of sigmatropic shifts; that is, that this 1,3-sigmatropic shift is not a concerted process.The results suggest that, although a concerted 1,5-sigmatropic shift is possible, the p-semidine rearrangement of 18 is not characterized by one.It this case, however, a firm decision is not possible.Finally, the results indicate that disproportionation involves one (or both) of the two semidine rearrangement intermediates.The most likely one is that of the p-semidine.Rapid redox reaction of this intermediate (26), formed in the rate-determining step, with a second molecule of 18 can then lead to the p-semidine by removal of Cl+ and to disproportionation by scission of the central C-C bond of the intermediate.These paths account for the distribution of the products formed and the KIE of their formation.

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.