264146-78-3

Basic information

• Product Name: N¹,N⁴-bis(4-aminophenyl)-1,4-quinonediimine
• CAS NO: 264146-78-3
• Molecular Weight: 288.352
• Mol File: 264146-78-3.mol

Chemical Properties

• CAS DataBase Reference: N¹,N⁴-bis(4-aminophenyl)-1,4-quinonediimine(CAS DataBase Reference)
• NIST Chemistry Reference: N¹,N⁴-bis(4-aminophenyl)-1,4-quinonediimine(264146-78-3)
• EPA Substance Registry System: N¹,N⁴-bis(4-aminophenyl)-1,4-quinonediimine(264146-78-3)

Safety Data

• Hazardous Substances Data: 264146-78-3(Hazardous Substances Data)

Upstream product

• 53760-27-3 4,4′-diaminodiphenylamine sulfate 
• 62-53-3 aniline 
• 350-46-9 4-Fluoronitrobenzene 
• 106-50-3 1,4-phenylenediamine 
• 41266-01-7 N¹,N⁴-bis(4-nitrophenyl)-1,4-benzenediamine 
• 4958-10-5 N¹,N⁴-bis(4-aminophenyl)-1,4-benzenediamine 
• 16245-77-5 p-phenylenediammonium sulfate 
• 537-65-5 4,4'-diaminodiphenylamine 

Downstream Products

• 651048-13-4 N'',N'''-bis(2'',4''-nitrophenyl)-N,N'-bis(4'-aminophenyl)-1,4-benzenediamine 
• 651048-12-3 N'',N'''-bis(2''-nitrophenyl)-N,N'-bis(4'-aminophenyl)-1,4-benzenediamine 
• 651048-11-2 N'',N'''-bis(4''-nitrophenyl)-N,N'-bis(4'-aminophenyl)-1,4-benzenediamine 
• 651048-17-8 N'',N'''-bis(2''-nitrophenyl)-N,N'-bis(4'-aminophenyl)-1,4-quinonediimine 
• 725216-42-2 N'',N'''-bis(4''-nitrophenyl)-N,N'-bis(4'-aminophenyl)-1,4-quinonediimine 
• 651048-18-9 N'',N'''-bis(2'',4''-dinitrophenyl)-N,N'-bis(4'-aminophenyl)-1,4-quinonediimine 
• 4958-10-5 N¹,N⁴-bis(4-aminophenyl)-1,4-benzenediamine 

Relevant articles and documents

An aniline trimer-based multifunctional sensor for colorimetric Fe3+, Cu2+ and Ag+ detection, and its complex for fluorescent sensing of L-tryptophan

The detection of metal ions and amino acids by the aniline oligomer-based receptor has not been reported yet, to the best of our knowledge. In this study, an efficient multifunctional cation-amino acid sensor (CAS) with aniline moiety and chiral thiourea binding site was synthesized by the reaction of aniline trimer and (S)-(+)-1-phenyl ethyl isothiocyanate. CAS can sense Fe3+, Cu2+, Ag+ ions, and L-tryptophan. These results can be recognized by the naked eye. The appropriate pH range for the quantitative analysis of Fe3+, Cu2+, and Ag+ by CAS in DMSO/water (30 vol% water) was evaluated. The interaction between CCS and metal ions was analyzed by 1H NMR titration. The detection limits of CAS for the Cu2+, Ag+, and Fe3+ were 0.214, 0.099, and 0.147 μM, respectively. Moreover, the CAS[sbnd]Cu2+ complex can act as a turn-on fluorescence sensor for L-tryptophan. On the contrary, there is no response upon the addition of other amino acids, such as L-histidine, L-proline, L-phenylalanine, L-threonine, L-methionine, L-tyrosine, and L-cystine to CAS[sbnd]Cu2+ complex.

COMPOSITIONS OF OLIGOANILINES AND METHODS OF MAKING AND USING

Compositions of oligoanilines with higher purity, methods of making and using thereof, are provided. The compositions are produced in large scale with larger yield using simple purification techniques such as washing. Methods have been developed that allow large scale synthesis of oligoaniline compounds with the following benefits: (i) higher purity; (ii) larger yield of oligoaniline compounds; (iii) simple purification that does not require complicated techniques such as liquid chromatograph; (iv) lower cost; and (v) full characterization. The highly pure oligoaniline compositions can be used as reducing or oxidizing agent in a redox reaction. The oligoaniline compositions have colors and can be used as dyes, i.e. redox active dyes in a redox reaction, as intermediates for the development of conductive elastomers, or as catalysts.

DERIVATIVES OF PPD USEFUL FOR COLORING HAIR AND SKIN

The is provided a compound of formula I or II or physiologically acceptable salts or solvates, or oxidised derivatives thereof: where R1 to R3, R13 and R14 are as defined herein. Also disclosed herein are methods of dyeing hair or (temporarily) tattooing the skin using the compounds of formula I or II (or physiologically acceptable salts or solvates, or oxidised derivatives thereof) in a suitable composition.

Large-Scale Synthesis of Aniline Trimers in Different Oxidation States

Polyanilines are an important class of organic compounds, due to their utility in a large variety of applications. In contrast, oligo?-anilines have been employed far more sporadically, in large part reflecting an absence of refined synthetic approaches. Herein, we report, for the first time, a relatively large-scale strategy to generate highly pure aniline trimers at different oxidation states with excellent yields (90-97percent).

A Degradable and Recyclable Photothermal Conversion Polymer

Decomposition and repolymerization of conjugated polymers offer great promise for developing recyclable photothermal conversion materials, which yet remain challenging. Herein, a crosslinked conjugated polymer based on a dynamic covalent bond of Schiff base is developed. This polymer possesses photothermal conversion efficiency as high as 90.4 %. Decomposition of the polymer under specialized conditions is corroborated by various characterizations. The kinetics study is also investigated to understand this degradation process. Furthermore, those decomposed species can be repolymerized back to conjugated polymers which possess the same photothermal conversion efficiency as the pristine polymer. Such a degradable and recyclable photothermal polymer is successfully used as a heat source for photothermal-electrical conversion to generate Seebeck voltage under either near infrared (NIR) irradiation or solar illumination.

Synthesis and characterization of organo-soluble aniline oligomer-based electroactive doped with gold nanoparticles, and application to electrochemical sensing of ascorbic acid

Organo-soluble aniline oligomer-based electroactive polyimide (EPI) doped with gold nanoparticles (GNPs) applied in sensing ascorbic acid (AA) was presented. Conjugated aniline trimer (AT3) and aniline tetramer (AT4) were synthesized and characterized via 1H NMR, FTIR, and MS spectroscopic studies. Subsequently, the organo-soluble electroactive polyimide (EPI) was prepared by chemical imidization of electroactive poly(amic acid) (EPAA), followed by characterization through FTIR and GPC analyses. Moreover, formation of reduced gold nanoparticles (GNPs) upon the surface of EPI was confirmed by XRD, SEM-EDS, TEM and ICP-OES. Based on CV studies, the redox capability of as-prepared materials was found to show a decreasing trend of EPI-4G > EPI-4 > EPI-3. The as-prepared EPI-4G modified carbon paste electrode (CPE) turned out best in sensing AA at lower oxidative potential with good sensitivity, relative low detection limit, broad linear dynamic range and best selectivity for a tertiary mixture of ascorbic acid (AA)/dopamine (DA)/uric acid (UA) compared to the other tested electrodes.

New syntheses of N,N′-diaryl-substituted quinone diimines: I. Synthesis of N,N′-bis(4-aminophenyl)-1,4-benzoquinone diimine

Oxidative condensation of p-phenylenediamine by the action of K2S2O8 in acetic acid afforded N,N′-bis(4-aminophenyl)-1,4-benzoquinone diimine which underwent self-condensation on heating. Acetylation of the title compound

Oxidative polymerization of p-phenylenediamine

Oxidative polymerization of p-phenylenediamine in a hydrochloric acid solution yields not a polyquinoxaline polymer as described in the literature but a modified poly(1,4-benzoquinonediimine-N,N′-diyl-1,4-phenylene) analogous to polyaniline known as pernigraniline. A new scheme of oxidative polymerization of p-phenylenediamine was suggested.

Synergistic effect of electroactivity and hydrophobicity on the anticorrosion property of room-temperature-cured epoxy coatings with multi-scale structures mimicking the surface of Xanthosoma sagittifolium leaf

A novel method is introduced to fabricate an electroactive epoxy (EE) coating with structured hydrophobic surfaces using an environmentally friendly process for anticorrosion application. First of all, the electroactive amine-capped aniline trimer (ACAT) was used as a curing agent to cure the epoxy resin and additionally provided electroactivity to the cured epoxy resin. The EE coating was cured at room temperature without using any solvent. The increased amount of the ACAT component in the EE coating not only accelerated the curing process but also promoted the thermal stability and anticorrosion performance. Subsequently, the multi-scale papilla-like structures on the surface of the Xanthosoma sagittifolium leaf were successfully replicated on the surface of the EE coating using PDMS as a negative template, as evidenced by the SEM investigation. The resulting hydrophobic electroactive epoxy (HEE) coating with the replicated nanostructured surface showed a hydrophobic characteristic with a water contact angle close to 120°. The developed HEE coating exhibited superior anticorrosion performance in electrochemical corrosion tests as its corrosion rate is better than that of the bare steel substrate by a factor of 450. The significantly improved corrosion protection is attributed to, besides the steel substrate isolated by the coating, the synergistic effect of electroactivity and hydrophobicity from the HEE coatings with the multi-scale structures mimicking the surface of the Xanthosoma sagittifolium leaf.

Advanced anticorrosive materials prepared from amine-capped aniline trimer-based electroactive polyimide-clay nanocomposite materials with synergistic effects of redox catalytic capability and gas barrier properties

In this study, preparation and electrochemical corrosion protection studies of a series of polyimide-Clay nanocomposite (PCN) materials were first presented. Subsequently, the as-prepared PCN materials were characterized by FTIR, XRD and TEM studies. In-situ monitoring for redox behavior of as-prepared PCN materials was identified by UV-visible and CV studies. It should be noted that PCN coating was found to reveal advanced corrosion protection effect on cold-rolled steel (CRS) electrode as compared to that of neat non-electroactive polyimide coating based on series of electrochemical corrosion measurements in 5 wt% NaCl electrolyte. Enhancement of corrosion protection of PCN coatings on CRS electrode may be interpreted by following two possible reasons: (1) redox catalytic capabilities (i.e., electroactivity) of ACAT units existed in electroactive PCN may induce formation of passive metal oxide layers on CRS electrode, as evidenced by SEM and ESCA studies. (2) well-dispersed layered organophilic clay platelets embedded in electroactive PCN matrix could functioned as hinder with high aspect ratio to effectively enhance the oxygen barrier property of PCN, as evidenced by GPA.