4316-54-5

Usage

Uses

Used in Pharmaceutical Production:
3-Methyltriphenylamine is used as a key intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and medicines.
Used in Agrochemical Production:
3-METHYLTRIPHENYLAMINE is utilized as a raw material in the production of agrochemicals, helping to create effective pesticides and other agricultural products.
Used in Dye Manufacturing:
3-Methyltriphenylamine is employed as a precursor in the synthesis of dyestuffs, contributing to the creation of a wide range of colors for various applications.
Used in Performance Materials:
3-METHYLTRIPHENYLAMINE is used as a component in the development of performance materials, such as advanced polymers and composites, due to its unique properties.
Used in Metal-Organic Frameworks:
3-Methyltriphenylamine is used as a ligand in the creation of metal-organic frameworks, which have potential applications in gas storage, catalysis, and sensing.
Used in Optoelectronics:
As an effective hole-transporter, 3-Methyltriphenylamine is utilized in the development of optoelectronic devices, such as organic light-emitting diodes (OLEDs) and solar cells, to improve their performance and efficiency.

InChI:InChI=1/C19H17N/c1-16-9-8-14-19(15-16)20(17-10-4-2-5-11-17)18-12-6-3-7-13-18/h2-15H,1H3

Upstream product

• 108-41-8 1-chloro-3-methylbenzene 
• 5864-44-8 potassium diphenylamide 
• 95-49-8 2-methylchlorobenzene 
• 591-50-4 iodobenzene 
• 1205-64-7 3-Methyldiphenylamine 
• 591-17-3 meta-bromotoluene 
• 122-39-4 diphenylamine 
• 108-44-1 1-amino-3-methylbenzene 
• 98-98-6 2-Picolinic acid 
• 586-62-9 Terpinolene 
• 625-95-6 3-Iodotoluene 
• 66003-76-7 Diphenyliodonium triflate 
• 108-94-1 cyclohexanone 
• 13482-23-0 4-methoxycyclohexanone 

Downstream Products

• 65181-78-4 4,4'-bis(m-tolylphenylamino)biphenyl 
• 717880-57-4 C₁₉H₁₆BrN 
• 1460283-98-0 C₁₉H₁₄Br₃N 

Relevant academic research and scientific papers

A Pd/Cu-Free magnetic cobalt catalyst for C-N cross coupling reactions: synthesis of abemaciclib and fedratinib

Herein, the synthesis of a nano-catalytic system comprising magnetic nanoparticles as the core and edible natural ligands bearing functional groups as supports for cobalt species is described. Subsequent to its characterization, the efficiency of the catalyst was investigated for C-N cross-coupling reactions using assorted derivatives of amines and aryl halides. This novel and easily accessible Pd- and Cu-free catalyst exhibited good catalytic activity in these reactions using γ-valerolactone (GVL) at room temperature; good recyclability bodes well for the future application of this strategy. The introduced catalytic system is attractive in view of the excellent efficiency in an array of coupling reactions and its versatility is illustrated in the synthesis of abemaciclib and fedratinib, which are FDA-approved new and significant anti-cancer medicinal compounds that are prepared under green reaction conditions.

Synthesis of unsymmetrically substituted triarylaminesviaacceptorless dehydrogenative aromatization using a Pd/C andp-toluenesulfonic acid hybrid relay catalyst

An efficient and convenient procedure for synthesizing triarylamines based on a dehydrogenative aromatization strategy has been developed. A hybrid relay catalyst comprising carbon-supported Pd (Pd/C) andp-toluenesulfonic acid (TsOH) was found to be effective for synthesizing a variety of triarylamines bearing different aryl groups starting from arylamines (diarylamines or anilines), using cyclohexanones as the arylation sources under acceptorless conditions with the release of gaseous H2. The proposed reaction comprises the following relay steps: condensation of arylamines and cyclohexanones to produce imines or enamines, dehydrogenative aromatization of the imines or enamines over Pd nanoparticles (NPs), and elimination of H2from the Pd NPs. In this study, an interesting finding was obtained indicating that TsOH may promote the dehydrogenation.

N/O-doped carbon as a "solid ligand" for nano-Pd catalyzed biphenyl- and triphenylamine syntheses

A series of N/O-doped porous carbon supported nanopalladium catalysts have been successfully prepared, in which the N/O doped carbons were controllably produced via polypyrrole/furan synthesis followed by carbonization. These catalysts exhibit good performance in biphenylamine and triphenylamine syntheses with nitrobenzene and cyclohexanone as starting materials. Their catalytic activity can be tuned efficiently by the N/O functional groups on the carbon surface. TEM, XRD, XPS and laser Raman methods were applied to probe the structure of these catalysts. These results indicate that the Pd nanoparticles were supported on N/O-doped porous carbon via the "coordination" between Pd nanoparticles and N/O functional groups including O-CO, CN and tertiary nitrogen, and better catalytic performance was obtained if carbon with the highest N-species loading was used as the support. In addition, a mechanistic study proved that the reaction starts with the catalytic reduction of nitrobenzene with cyclohexanone as the hydrogen source. During this reaction, aniline was formed and the cyclohexanone was transformed into phenol. Then biphenylamine and triphenylamine were generated through the reaction of aniline and cyclohexanone. This work should facilitate the controllable preparation of carbon supported nanocatalysts with specific activity, and open up a promising pathway for the development of new methodologies for N-containing fine chemical synthesis.

Synthesis of Triarylamines via Sequential C-N Bond Formation

A one-pot domino N-arylation protocol is described using diaryliodonium reagents under copper catalysis. The reaction uses both aryl groups of the diaryliodonium reagent to generate triarylamines starting from simple anilines, representing an atom-economical preparation of an important class of organic material building blocks.

An efficient heterogeneous ligand free C-N coupling reaction catalyzed by palladium supported on magnetic nanoparticles

The catalytic activity of palladium supported on magnetic nanoparticles in the amination coupling reaction of different nitrogen containing substrates with aryl halides was investigated. C-N bond formation was achieved in moderate to excellent yields and the catalyst could be separated by magnetic decantation.

A 1 - (2- [...] ) b cyclohexyl phosphine and its preparation method and application (by machine translation)

The invention provides 1-(2-arylindenyl) dicyclohexylphosphine which takes a good catalytic effect in carbon-nitrogen coupling reaction of chlorinated or brominated aromatic hydrocarbons and diphenylamine and has the general formulas shown in the specification. According to the preparation method of 1-(2-arylindenyl) dicyclohexylphosphine, 2-aryl indene serving as a raw material reacts with n-butyllithium in the presence of high-purity nitrogen to obtain 1-(2-arylindenyl) dicyclohexylphosphine. 1-(2-arylindenyl) dicyclohexylphosphine and the preparation method and application thereof have the beneficial effects that A, B, C, D, E and F can exist in the air stably; a catalyst consisting of a compound D and palladium dibenzylacetone can catalyze reactions between various chlorinated aromatic hydrocarbons and diphenylamine and the highest yield is high up to 82%; the reactions between brominated aromatic hydrocarbons with high steric hindrance and diphenylamine can be catalyzed by the catalyst and the highest yield is high up to 85%; the reactions between chlorinated or brominated heterocyclic aromatic hydrocarbons and diphenylamine can be catalyzed by the catalyst and the highest yield is high up to 62%.

The heterogeneous catalyst using the same and method of manufacturing hydroxytriarylamine compd. (by machine translation)

PROBLEM TO BE SOLVED: To provide an industrially-useful heterogeneous catalyst for coupling reaction, and a method for producing a triarylamine compound and/or triarylamine polymer using the heterogeneous catalyst. SOLUTION: The heterogeneous catalyst for coupling reaction includes a carrier, a palladium compound, and tri (tert-butyl) phosphine, and is characterized in that the palladium compound content in weight is 0.03 to 0.2 times the carrier weight in terms of palladium atom and the tri (tert-butyl) phosphine content in mole is 0.6 to 12 times one palladium atom mole in the palladium compound. In addition, the heterogeneous catalyst is used. COPYRIGHT: (C)2013,JPO&INPIT

Pd-indenyl-diphosphine: An effective catalyst for the preparation of triarylamines

A new Buchwald-type diphosphine ligand has been developed for applications in Pd-catalyzed amination reactions towards the preparation of triarylamines. The catalyst can be used to perform the amination of a diverse array of aryl and heteroaryl chlorides.

Nickel-catalyzed triarylamine synthesis: Synthetic and mechanistic aspects

An improved protocol was described for the amination of chloroarenes with diarylamines under NiCl2(PCy3)2 catalysis in the presence of a Grignard reagent as base. This method fully suits bromo-/iodoarene substrates as well, and even is expanded to certain aryl tosylates. A preliminary investigation into the mechanism suggests that this amination reaction might proceed through NiI and NiIII intermediates rather than via the usually expected Ni0-Ni II cycle.

Simple and convenient methods for N-arylation of heterocycles and diphenylamine

N-Arylation of NH-heterocycles and diphenylamine with various aryl halides, using a readily accessible ligand-free potassium tert-butoxide/iron(III) oxide/dimethyl sulfoxide reagent system, gives the corresponding N-aryl derivatives in 47-97% yields. Georg Thieme Verlag Stuttgart . New York.