437-25-2

Usage

Uses

Used in Research Applications:
4-Fluoro-N,N-diphenylbenzenamine is employed as a research chemical, serving as a valuable compound for scientific investigations and experiments. Its unique structure and properties make it a useful tool in the exploration of various chemical and physical phenomena.
Used in Industrial Applications:
In the industrial sector, 4-Fluoro-N,N-diphenylbenzenamine is used as a chemical intermediate, playing a crucial role in the synthesis of more complex molecules and materials. Its presence in the production process can contribute to the development of new products and technologies.
Used in Pharmaceutical Development:
4-Fluoro-N,N-diphenylbenzenamine is utilized as a building block in the pharmaceutical industry, where it can be incorporated into the design and synthesis of new drug molecules. Its potential to form various chemical bonds and interactions with other compounds makes it a promising candidate for the development of novel therapeutic agents.
Used in Material Science:
In the field of material science, 4-Fluoro-N,N-diphenylbenzenamine is used as a component in the creation of advanced materials with specific properties. Its incorporation into the molecular structure of these materials can lead to the enhancement of their performance, such as improved stability, reactivity, or conductivity.

Upstream product

• 352-34-1 4-fluoro-1-iodobenzene 
• 122-39-4 diphenylamine 
• 2350-01-8 4-aminotriphenylamine 
• 17425-91-1 N-(trimethylsilyl)-diphenylamine 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 352-33-0 1-Chloro-4-fluorobenzene 
• 108-90-7 chlorobenzene 
• 62-53-3 aniline 
• 350-46-9 4-Fluoronitrobenzene 
• 66003-76-7 Diphenyliodonium triflate 
• 371-40-4 4-fluoroaniline 
• 1195-45-5 para-fluorophenyl isocyanate 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 108-86-1 bromobenzene 

Downstream Products

• 57103-14-7 p-fluorophenyl-9 carbazole 

Relevant academic research and scientific papers

Benzyloxycalix[8]arene supported Pd-NHC cinnamyl complexes for Buchwald-Hartwig C-N cross-couplings

The scalable synthesis of Pd-NHC cinnamyl complexes supported on benzyloxycalix[8]arene is reported. These catalysts are very active for Buchwald-Hartwig cross-coupling reactions, allowing the coupling of aryl chlorides and bromides with a wide variety of alkyl and aryl amines using low catalytic loadings. The supported complexes also successfully afforded attractive unsymmetrical triarylamines, and in one case, promoted the synthesis of an unprecedented Pd-catalyzed C-H activation product. Thanks to the calixarenic support, the target products could be isolated with low levels of residual palladium, and in some cases, even below the restrictive toxic metal standards applied by the pharmaceutical industry. Through an easy to implement procedure, these perfectly characterised catalysts thus combine the best of homogeneous and heterogeneous catalysis: high efficiency (similar to or even better than the corresponding homogeneous complexes) and low Pd leaching levels expected from heterogeneous catalysts.

Transition-Metal-Free Diarylation of Isocyanates with Arynes

A facile method for the transition-metal-free diarylation of isocyanates with arynes in the presence of cesium fluoride has been developed, which affords functionalized diaryl amines in moderate to excellent yields. This reaction has good functional group tolerance and provides excellent regioselectivity by utilizing a methoxy-substituted aryne precursor.

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.

Buchwald–Hartwig Amination of Nitroarenes

The Buchwald–Hartwig amination of nitroarenes was achieved for the first time by using palladium catalysts bearing dialkyl(biaryl)phosphine ligands. These cross-coupling reactions of nitroarenes with diarylamines, arylamines, and alkylamines afforded the corresponding substituted arylamines. A catalytic cycle involving the oxidative addition of the Ar?NO2 bond to palladium(0) followed by nitrite/amine exchange is proposed based on a stoichiometric reaction.

Nano PdAu Bimetallic Alloy as an Effective Catalyst for the Buchwald-Hartwig Reaction

It is highly challenging but desirable to develop efficient heterogeneous catalysts for C-Cl bond activation in coupling reactions. Here, we succeeded in synthesizing bimetallic Pd-Au nanoparticles through a convenient one-pot wet chemical route. The composition and alloyed structure of the as-prepared nanoparticles were fully characterized. We have evaluated the catalytic activity of these Pd-Au alloy catalysts in Buchwald-Hartwig reactions of aryl chlorides. The excellent catalytic activity of the as-obtained Pd-Au nanoparticles indicates that exploiting the catalytic power of nano-alloy catalysts could enable effective C-Cl bond activation suitable for cross-coupling reactions.

Solvent-Free Buchwald-Hartwig (Hetero)arylation of Anilines, Diarylamines, and Dialkylamines Mediated by Expanded-Ring N-Heterocyclic Carbene Palladium Complexes

A highly efficient solvent-free protocol for the Buchwald-Hartwig (hetero)arylation of anilines, diarylamines, and dialkylamines mediated by the expanded-ring N-heterocyclic carbene palladium complex (THP-Dipp)Pd(cinn)Cl [THP-Dipp = 1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene; cinn = cinnamyl, 3-phenylallyl] was developed. The catalytic protocol was efficient for the coupling of amines and (hetero)aryl chlorides and bromides bearing donor, acceptor, and bulky substituents.

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.

Photochemical Synthesis of Complex Carbazoles: Evaluation of Electronic Effects in Both UV- and Visible-Light Methods in Continuous Flow

An evaluation of both a visible-light- and UV-light-mediated synthesis of carbazoles from various triarylamines with differing electronic properties under continuous-flow conditions has been conducted. In general, triarylamines bearing electron-rich groups tend to produce higher yields than triarylamines possessing electron-withdrawing groups. The incorporation of nitrogen-based heterocycles, as well as halogen-containing arenes in carbazole skeletons, was well tolerated, and often synthetically useful complementarity was observed between the UV-light and visible-light (photoredox) methods.

Method for producing hydroxytriarylamine (by machine translation)

PROBLEM TO BE SOLVED: To economically provide arylamines such as triarylamine. SOLUTION: An arylamine compound represented by formula (1) and an aryl compound having a leaving group represented by formula (2): X-Ar2-X1, are subjected to an arylamination reaction in the presence of a basic group, an alkaline metal salt and/or an alkaline earth metal salt, and an iron catalyst to thereby obtain arylamines such as triarylamines. In formula (1), Ar and Ar1are identical or different, and denote a substituted or non-substituted aryl group, and may be ring-condensed; and a denotes 1 or 2. In formula (2), X and X1are identical or different, and denote at least one leaving group selected from the group consisting of H or Br, I, CMs (mesylate), OTf (triflate) and OTs (tosylate), provided that X and X1are not simultaneously H, and have at least one leaving group; and Ar2denotes a substituted or non-substituted aryl group. COPYRIGHT: (C)2012,JPO&INPIT

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.