51786-49-3

Usage

Uses

Used in Organic Electronics Industry:
3,5-Dimethyltriphenylamine is used as a hole transporting material for its high thermal and chemical stability, as well as its high charge carrier mobility. This makes it suitable for applications in organic light-emitting diodes (OLEDs) and organic photovoltaic cells (OPVs), where it plays a crucial role in enhancing the performance and efficiency of these devices.
Used in Dye-Sensitized Solar Cells:
3,5-Dimethyltriphenylamine is being studied for its potential application as a sensitizer in dye-sensitized solar cells. Its properties may contribute to improving the light absorption and energy conversion efficiency of these solar cells.
Used in Organic Synthesis:
3,5-Dimethyltriphenylamine is also under investigation for its potential use in organic synthesis. Its unique structure and properties make it a promising building block for the synthesis of other organic compounds, opening up new avenues for the development of novel materials and applications in various industries.

Upstream product

• 108-86-1 bromobenzene 
• 2050-45-5 N-acetyl-3,5-dimethylaniline 
• 108-69-0 3,5-dimethylaminoaniline 
• 2320-30-1 3,5-dimethylcyclohexanone 
• 540-37-4 p-aminoiodobenzene 
• 99-12-7 5-nitro-m-xylene 
• 98-80-6 phenylboronic acid 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 54132-75-1 3,5-dimethylphenyl isocyanate 
• 515-42-4 sodium phenylsulfonate 
• 108-91-8 cyclohexylamine 
• 62-53-3 aniline 
• 100-63-0 phenylhydrazine 
• 108-90-7 chlorobenzene 

Downstream Products

• 1115314-63-0 (Z)-4-[(3,5-dimethylphenyl)phenylamino]-4-oxo-2-butenoic acid 
• 79735-32-3 1,3-dimethyl-10-phenyl-5,10-dihydrophenophosphazine 10-oxide 
• 79735-31-2 1,3-dimethyl-10-phenyl-5,10-dihydrophenophosphazine 

Relevant academic research and scientific papers

Electrochemical Reductive Arylation of Nitroarenes with Arylboronic Acids

The synthesis of diarylamine is extremely important in organic chemistry. Herein, a novel electrochemical reductive arylation of nitroarenes with arylboronic acids was developed. A variety of diarylamines were synthesized without the need for transition-metal catalysts. The reaction could be scaled up efficiently in a flow cell and several derivatization reactions were carried out smoothly. Cyclic voltammetry experiments and mechanism studies showed that acetonitrile, formic acid, and triethyl phosphite all played a role in promoting this reductive arylation transformation.

Chan-Evans-Lam C?N Coupling Promoted by a Dinuclear Positively Charged Cu(II) Complex. Catalytic Performance and Some Evidence for the Mechanism of CEL Reaction Obviating Cu(III)/Cu(I) Catalytic Cycle

In the present study, we report the synthesis of a series of copper(II) complexes with a wide range of ligands and their testing in the copper catalyzed Chan-Evans-Lam (CEL) coupling of aniline and phenylboronic acid. The efficiency of the coupling was directly connected with the ease of the reduction of Cu(II) to Cu(I) of the complexes. The most efficient catalyst was derived from 4-t-butyl-2,5-bis[(quinolinylimino)methyl]phenolate and two Cu(II) ions. Depending on the counter-anion nature and the concentration of the reaction mixture, the reaction can be directed to predominant C?N-bond formation. Forty-three derivatives of diphenylamine were prepared under the optimized conditions. The proposed mechanism of the catalysis was based on the reduction potential of a series of complexes, molecular weight measurements of the catalytic complex in MeOH and the kinetic studies of aniline and phenylboronic acid coupling. In addition, an 1H NMR experiment in a sealed NMR tube, without external oxygen supply available, proved that no complete Cu(II) to Cu(I) conversion was observed under the condition, ruling out the usually accepted mechanism of the C?N coupling, which included the oxygenation of the intermediately formed Cu(I) complexes after the key step of C?N conversion had already been completed. Instead, a mechanism was proposed, involving an oxygen molecule coordinated to two copper ions in the key C?N bond formation without any detectable conversion of the Cu(II) complexes to Cu(I).

Transition-metal-free synthesis of aromatic amines via the reaction of benzynes with isocyanates

An unexpected reaction between benzynes and isocyanates to generate aromatic amines has been developed under transition-metal-free conditions. The in situ prepared anions formed through cleavage of the N–C bond in isocyanates, reacted with aryne precursor

Synthesis of Arylamines via Non-Aerobic Dehydrogenation Using a Palladium/Carbon-Ethylene System

The reaction of cyclohexanones with amines proceeded under an ethylene atmosphere in the presence of a catalytic amount of palladium/carbon to afford a variety of arylamines in good to high yields. The present reaction was carried out under completely non-aerobic conditions, and which is in contrast with the previously reported aerobic system. has wide applicability affording a variety of aromatic amines, and co-product of the reaction is only gaseous ethane. Thus, this method is environmentally friendly. This protocol was applied intramolecularly to provide a novel method for the construction of quinoline and isoquinoline compounds. (Figure presented.).

Versatile routes for synthesis of diarylamines through acceptorless dehydrogenative aromatization catalysis over supported gold-palladium bimetallic nanoparticles

Diarylamines are an important class of widely utilized chemicals, and development of diverse procedures for their synthesis is of great importance. Herein, we have successfully developed novel versatile catalytic procedures for the synthesis of diarylamines through acceptorless dehydrogenative aromatization. In the presence of a gold-palladium alloy nanoparticle catalyst (Au-Pd/TiO2), various symmetrically substituted diarylamines could be synthesized starting from cyclohexylamines. The observed catalysis of Au-Pd/TiO2 was heterogeneous in nature and Au-Pd/TiO2 could be reused several times without severe loss of catalytic performance. This transformation needs no oxidants and generates molecular hydrogen (three equivalents with respect to cyclohexylamines) and ammonia as the side products. These features highlight the environmentally benign nature of the present transformation. Furthermore, in the presence of Au-Pd/TiO2, various kinds of structurally diverse unsymmetrically substituted diarylamines could successfully be synthesized starting from various combinations of substrates such as (i) anilines and cyclohexanones, (ii) cyclohexylamines and cyclohexanones, and (iii) nitrobenzenes and cyclohexanols. The role of the catalyst and the reaction pathways were investigated in detail for the transformation of cyclohexylamines. The catalytic performance was strongly influenced by the nature of the catalyst. In the presence of a supported gold nanoparticle catalyst (Au/TiO2), the desired diarylamines were hardly produced. Although a supported palladium nanoparticle catalyst (Pd/TiO2) gave the desired diarylamines, the catalytic activity was inferior to that of Au-Pd/TiO2. Moreover, the activity of Au-Pd/TiO2 was superior to that of a physical mixture of Au/TiO2 and Pd/TiO2. The present Au-Pd/TiO2-catalyzed transformation of cyclohexylamines proceeds through complex pathways comprising amine dehydrogenation, imine disproportionation, and condensation reactions. The amine dehydrogenation and imine disproportionation reactions are effectively promoted by palladium (not by gold), and the intrinsic catalytic performance of palladium is significantly improved by alloying with gold. One possible explanation of the alloying effect is the formation of electron-poor palladium species that can effectively promote the β-H elimination step in the rate-limiting amine dehydrogenation.

Room-Temperature CuI-Catalyzed Amination of Aryl Iodides and Aryl Bromides

A general and effective CuI/N′,N′-diaryl-1H-pyrrole-2-carbohydrazide catalyst system was developed for the amination of aryl iodides and bromides at room temperature with good chemoselectivity between -OH and -NH2 groups. Only 5 mol % of CuI and ligands was needed in this protocol to effect the amination of various aryl bromides and aryl iodides with a wide range of aliphatic and aryl amines (1.3 equiv).

The invention relates to a N, N - disubstituted hydrazide as ligand copper catalysis C - N coupling method (by machine translation)

The invention discloses a to N, N - disubstituted hydrazide as ligand copper catalysis C - N coupling method, the method uses the aromatic halides with amine compound as a raw material, in order to alcohol compound as the solvent, in order to copper or copper compound as a catalyst, in order to as formula I or formula II as shown by a N, N - disubstituted hydrazide as a ligand, the presence of a base, in the 10 - 130 °C generating C - N coupled reaction for generating N - aryl compound: the invention mild reaction conditions, high chemical selectivity, substrate and wide range of application, simplicity of operation, product is simple and easy to separation and environmental protection, the obtained product yield is higher. Wherein R1, R2 is selected from methyl, phenyl, 4 - methoxyphenyl, 4 - nitro-phenyl, 2 - methylphenyl, 2 - isopropyl phenyl; R3 is hydrogen or methoxy. (by machine translation)

A and quinoline derivatives thereof in organic electroluminescent the application in the field of

The invention relates to a compounded quindoline derivative as shown in the formula (1), wherein Ar1 and Ar2 are respectively independently selected from C6-C40 substituted or unsubstituted aromatic groups, or can be connected to form C3-C40 substituted or unsubstituted fused aromatic groups. The invention also relates to an application of the compound in organic electroluminescence devices, especially to an application of the compound used as a luminescence host material of OLED devices.

Highly Chemoselective Iridium Photoredox and Nickel Catalysis for the Cross-Coupling of Primary Aryl Amines with Aryl Halides

A visible-light-promoted iridium photoredox and nickel dual-catalyzed cross-coupling procedure for the formation C?N bonds has been developed. With this method, various aryl amines were chemoselectively cross-coupled with electronically and sterically diverse aryl iodides and bromides to forge the corresponding C?N bonds, which are of high interest to the pharmaceutical industries. Aryl iodides were found to be a more efficient electrophilic coupling partner. The coupling reactions were carried out at room temperature without the rigorous exclusion of molecular oxygen, thus making this newly developed Ir-photoredox/Ni dual-catalyzed procedure very mild and operationally simple.