51786-49-3

Basic information

• Product Name: 3,5-Dimethyltriphenylamine
• Synonyms: 3,5-dimethyltriphenylamine;Benzenamine,3,5-dimethyl-N-phenyl-;3,5imethyltriphenylamine;3,5-Dimethyl-N-phenylbenzenamine
• CAS NO: 51786-49-3
• Molecular Formula: C₁₄H₁₅N
• Molecular Weight: 273.37
• Mol File: 51786-49-3.mol
• Article Data: 31

Chemical Properties

• Melting Point: 57 °C
• Boiling Point: 319.5±11.0 °C(Predicted)
• Appearance: /
• Density: 1.049±0.06 g/cm3(Predicted)
• PKA: 1.15±0.50(Predicted)
• CAS DataBase Reference: 3,5-Dimethyltriphenylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dimethyltriphenylamine(51786-49-3)
• EPA Substance Registry System: 3,5-Dimethyltriphenylamine(51786-49-3)

Safety Data

• Hazardous Substances Data: 51786-49-3(Hazardous Substances Data)

Usage

General Description

3,5-Dimethyltriphenylamine is a chemical compound with the molecular formula C24H21N. It is a substituted triphenylamine, where three phenyl groups are attached to the amine nitrogen atom. 3,5-Dimethyltriphenylamine is a dark-colored solid that is soluble in common organic solvents. 3,5-Dimethyltriphenylamine is commonly used as a hole transporting material in organic electronic devices such as organic light-emitting diodes (OLEDs) and organic photovoltaic cells (OPVs), due to its high thermal and chemical stability, as well as its high charge carrier mobility. Additionally, it has been studied for its potential application as a sensitizer in dye-sensitized solar cells. The compound is also under investigation for its potential use in organic synthesis and as a building block for the synthesis of other organic compounds.

Upstream product

• 108-69-0 3,5-dimethylaminoaniline 
• 108-90-7 chlorobenzene 
• 100-63-0 phenylhydrazine 
• 515-42-4 sodium phenylsulfonate 
• 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 
• 108-91-8 cyclohexylamine 
• 62-53-3 aniline 
• 108-86-1 bromobenzene 
• 22445-41-6 3,5-dimethylphenyl iodide 

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 articles and documents

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.

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

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.