35548-96-0

Basic information

• Product Name: N-(4-iminocyclohexa-2,5-dien-1-ylidene)aniline
• Synonyms: 3-Imino-6-phenylimino-cyclohexa-1,4-diene; benzenamine, N-(4-imino-2,5-cyclohexadien-1-ylidene)-; N-(4-Imino-2,5-cyclohexadien-1-ylidene)aniline; N-(4-Iminocyclohexa-2,5-dien-1-ylidene)aniline
• CAS NO: 35548-96-0
• Molecular Formula: C₁₂H₁₀N₂
• Molecular Weight: 182.2212
• Mol File: 35548-96-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 281.661°C at 760 mmHg
• Flash Point: 124.145°C
• Density: 1.071g/cm³
• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.594
• CAS DataBase Reference: N-(4-iminocyclohexa-2,5-dien-1-ylidene)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-iminocyclohexa-2,5-dien-1-ylidene)aniline(35548-96-0)
• EPA Substance Registry System: N-(4-iminocyclohexa-2,5-dien-1-ylidene)aniline(35548-96-0)

Safety Data

• Hazardous Substances Data: 35548-96-0(Hazardous Substances Data)

Upstream product

• 62-53-3 aniline 
• 101-54-2 N-phenylphenylene-1,4-diamine 
• 60-29-7 diethyl ether 
• 7732-18-5 water 
• 70278-00-1 N,N-dichloro-aniline 
• 56-23-5 tetrachloromethane 
• 156-10-5 p-nitrosodiphenylamine 

Downstream Products

• 156-10-5 p-nitrosodiphenylamine 
• 2406-04-4 4-(phenylimino)cyclohexa-2,5-dienone 
• 108673-54-7 [1,4]benzoquinon-[4-(4-amino-anilino)-phenylimine]-phenylimine 
• 71338-14-2 2,5-bis-(4-anilino-anilino)-[1,4]benzoquinone-imine-phenylimine 
• 102754-67-6 2-amino-5-anilino-[1,4]benzoquinone-bis-phenylimine 
• 106-51-4 p-benzoquinone 
• 4435-12-5 azophenin 
• 115080-25-6 [1,4]benzoquinone-mono-[4-(4-phenylimino-cyclohexa-2,5-dienylidenamino)-phenylimine] 

Relevant articles and documents

Electrochemical generation of a Michael acceptor: A green method for the synthesis of 4-amino-3-(phenylsulfonyl)diphenylamine derivatives

Electrochemical oxidation of 4-aminodiphenylamine in aqueous solution and in the presence of some arylsulfinic acids as nucleophiles was studied and its reaction mechanism was discussed. Using the voltammetric data, a one-pot and environmentally friendly

Electrochemical polymerization of aniline investigated using on-line electrochemistry/electrospray mass spectrometry

A thin-layer electrochemical flow cell coupled on-line with electrospray mass spectrometry (EC/ES-MS) was used to investigate the soluble products from the controlled-potential anodic polymerization of aniline in H2O and H2O/CH3O H (1/1 v/v) with ammonium acetate and acetic acid or ammonium hydroxide as electrolytes (pH 4, 6.5, or 9). At a working electrode (glassy carbon) potential of 1.0 V versus Ag/AgCl, singly protonated aniline oligomers containing as many as 10 aniline units (10-mer) were observed in the ES mass spectra when the polymerization in H2O/CH3OH at pH 4 was carried out. The abundance of the higher n-mers decreased at higher solution pH and in 100% H2O at pH 4. Most of the oligomers were observed in more than one redox state ranging from fully oxidized (all imine nitrogens) to fully reduced (all amine nitrogens). The number of different redox states observed for the n-mers increased with increasing n. The structures of the reduced (m/z 185) and oxidized (m/z 183) aniline dimer ions (head-to-tail, tail-to- tail, or head-to-head) produced from the polymerization of aniline at pH 4, 6.5, and 9 in H2O/CH3OH were revealed to vary as a function of pH by comparison of their tandem mass spectrometry product ion spectra with the product ion spectra of the dimer standards. EC/ES-MS potential scan experiments, in which the working electrode current and major n-mer ions for n = 2, 3, and 4 were monitored as a function of electrode potential, were used to probe the growth mechanism to higher aniline oligomers. Under the conditions used, the controlled-current electrolytic process inherent to the operation of the ES ion source did not significantly influence the formation or nature of the oligomers observed. Beyond the current application, the results presented here serve to demonstrate the utility of EC/ES-MS as a tool in identifying the initial products of electropolymerization and in studying the products of electrode reactions in general.