6246-98-6

Basic information

• Product Name: N,N'-Diphenyl-1,4-benzoquinonediimine
• Synonyms: N,N'-Diphenyl-1,4-benzoquinonediimine;N,N'-(2,5-Cyclohexadiene-1,4-diylidene)bis(benzenamine);N,N'-(2,5-Cyclohexadiene-1,4-diylidene)dianiline;N,N'-[2,5-Cyclohexadiene-1,4-diylidene]bis(benzenamine);N,N'-Diphenyl-1,4-benzenediimine;N,N'-Diphenyl-p-benzoquinone diimine;p-Benzoquinonedianil
• CAS NO: 6246-98-6
• Molecular Formula: C₁₈H₁₄N₂
• Molecular Weight: 258.31716
• Mol File: 6246-98-6.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N,N'-Diphenyl-1,4-benzoquinonediimine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Diphenyl-1,4-benzoquinonediimine(6246-98-6)
• EPA Substance Registry System: N,N'-Diphenyl-1,4-benzoquinonediimine(6246-98-6)

Safety Data

• Hazardous Substances Data: 6246-98-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 2295, 1957 DOI: 10.1021/ja01566a074

Upstream product

• 56-23-5 tetrachloromethane 
• 122-39-4 diphenylamine 
• 62-53-3 aniline 
• 79-41-4 poly(methacrylic acid) 
• 74-31-7 N,N'-diphenyl-1,4-phenylenediamine 
• 615-93-0 2,5-Dichloro-1,4-benzoquinone 
• 64-19-7 acetic acid 
• 2350-01-8 4-aminotriphenylamine 
• 7722-84-1 dihydrogen peroxide 
• 4733-52-2 phthaloyl peroxide 
• 103-71-9 phenyl isocyanate 
• 106-51-4 p-benzoquinone 
• 2716-09-8 N,N'-dinitroso-N,N'-diphenyl-p-phenylenediamine 
• 64-17-5 ethanol 

Downstream Products

• 115760-32-2 2,5-di-p-toluidino-[1,4]benzoquinone-bis-phenylimine 
• 74-31-7 N,N'-diphenyl-1,4-phenylenediamine 
• 4435-12-5 azophenin 
• 106-51-4 p-benzoquinone 
• 615-93-0 2,5-Dichloro-1,4-benzoquinone 
• 325963-57-3 1-[4-(4-{3,6-Bis-[(E)-phenylimino]-cyclohexa-1,4-dienylsulfanyl}-phenylsulfanyl)-phenylsulfanyl]-3,6-bis-[(E)-phenylimino]-cyclohexa-1,4-diene 
• 911110-01-5 C₂₂H₂₄N₂S 
• 911110-02-6 C₂₆H₃₂N₂S₂ 
• 2716-09-8 N,N'-dinitroso-N,N'-diphenyl-p-phenylenediamine 
• 4071-18-5 2,2,4-trimethyl-6-oxo-2,6-dihydroquinoline 
• 106-34-3 quinhydrone 
• 18358-64-0 [1,4]benzoquinone-bis-(N-phenyl oxime ) 

Relevant articles and documents

Photosensitive oligomer formation and laser-induced polymerization of aniline on a gold electrode surface: A surface-enhanced Raman scattering study

The process of laser-induced electropolymerization of aniline was studied by in situ surface-enhanced Raman scattering (SERS) spectroscopy and cyclic voltammetry (CV). Formation of p-coupled aniline oligomers was confirmed at an electrode potential below the oxidation potential of aniline, and the oligomers were found to be the source compound for photoinduced electropolymerization.

Structure and properties of polyaniline as modeled by single-crystal oligomers

A single-crystal charge-transfer complex of a phenyl-end-capped tetramer of polyaniline has been synthesized and studied along with a similar dimer of polyaniline. Structural, optical, and electrochemical studies of these oligomers in various oxidation states provide detailed information which has been used to model the structure of polyaniline and its evolution during electronic doping. These studies of the polymer and its oligomers suggest that the emeraldine salt form of the polymer (50% doping per nitrogen) is a preferred low-energy structure. The preference for this structure leads to phase segregation in doped compositions having average doping levels less than 50%.

Electrochemical synthesis of N1,N4-diphenyl-2-(phenylsulfonyl)benzene-1,4-diamine derivatives: Introducing an example of ECDispCMich mechanism

The electrochemical oxidation of N,N'-diphenyl-l,4-phenylenediamine (DPD) has been studied using cyclic voltammetry and controlled potential coulometry methods. The results revealed that DPD shows two one-electron oxidation-reduction peaks. In the first step DPD via a single-electron process is converted to the related radical cation (DPD.+) and second step is conversion of DPD.+ to N-(4-(phenylimino) cyclohexa-2,5-dienylidene) benzenamine (CHD) via a one-electron/two-protons process. Our results also show that DPD.+ participates in disproportionation reaction and is converted to DPD and CHD. The rate of this reaction is pH dependent and increases with increasing pH. Furthermore, the electrochemical oxidation of DPD has been studied in the presence of arylsulfinic acids as nucleophiles. The results showed that electrochemically generated CHD participates in Michael addition reaction with arylsulfinic acids via a novel ECDispCMich mechanism and is converted to the N1,N4-diphenyl-2-(phenylsulfonyl)benzene-1,4-diamine derivatives. In this work, a facile and green electrochemical method for the synthesis of some new N1,N4-diphenyl-2-(phenylsulfonyl)benzene-1,4-diamine derivatives in good yields using controlled-potential electrolysis at a carbon electrode is also reported.

Solvent effect on the equilibrium constant of the chain reversible reaction of N,N'-diphenyl-1,4-benzoquinonediimine with 2,5-dichlorohydroquinone

The temperature dependences of the equilibrium constant K of the reversible chain reaction of N,N'-diphenyl-1,4-benzoquinonediimine with 2,5-dichlorohydroquinone in benzene, chlorobenzene, anisole, benzonitrile, and CCl4 were studied. The enthalpies and entropies of the reaction in these solvents were determined, and a linear dependence between them in aromatic solvents was found. The equilibrium constant depends on the solvent nature: the replacement of CCl4 by benzene at T = 298 K increases K from 13.6 to 140. The solvation effects are caused by several types of intermolecular interactions of participants of equilibrium with the medium. The decrease in K in the benzene-anisole-benzonitrile series is related, to a great extent, to complex formation with hydrogen bonding between 2,5-dichlorohydroquinone and the solvents. In anisole a charge-transfer complex is formed between the solvent and reaction product (2,5-dichloroquinone). The constant and enthalpy of the complexation were estimated.