101-23-5

Usage

Uses

Used in Organic Synthesis:
N-phenyl-3-(trifluoromethyl)aniline is utilized as a key intermediate in the synthesis of complex organic molecules. The presence of the trifluoromethyl group enhances the reactivity of the compound, allowing for the creation of a wide range of chemical products with tailored properties.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, N-phenyl-3-(trifluoromethyl)aniline serves as a building block for the development of new drugs. Its incorporation into drug candidates can impart beneficial pharmacological activities and improve the bioavailability and metabolic stability of the resulting pharmaceutical compounds. This makes it an important component in the design and synthesis of novel therapeutic agents.
Used in Medicinal Chemistry:
N-phenyl-3-(trifluoromethyl)aniline is employed as a structural element in medicinal chemistry to influence the properties of drug molecules. The trifluoromethyl group can affect the compound's interaction with biological targets, potentially leading to improved efficacy and selectivity in drug action. This makes it a valuable tool for the design of compounds with specific functions in the treatment of various diseases.

InChI:InChI=1/C13H10F3N/c14-13(15,16)10-5-4-8-12(9-10)17-11-6-2-1-3-7-11/h1-9,17H

Upstream product

• 1198183-95-7 phenyl 1H-imidazole-1-sulfonate 
• 98-16-8 3-trifluoromethylaniline 
• 66950-63-8 phenyl N,N-dimethylsulfamate 
• 401-81-0 m-trifluoromethylphenyl iodide 
• 62-53-3 aniline 
• 530-78-9 flufenamic acid 
• 98-80-6 phenylboronic acid 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 591-50-4 iodobenzene 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 325142-82-3 4,4,5,5-tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane 
• 100-68-5 methyl-phenyl-thioether 
• 1423-26-3 (meta-(trifluoromethyl)phenyl)boronic acid 
• 108-90-7 chlorobenzene 

Downstream Products

• 106336-12-3 3-trifluoromethyl-N,N-diphenylaniline 
• 61231-45-6 1-(N,N-diphenylamino)naphthalene 
• 77826-10-9 N-Phenyl-N-(3-trifluoromethyl-phenyl)-benzamide 
• 1609171-52-9 N-phenyl-N-(3-(trifluoromethyl)phenyl)naphthalene-1-amine 
• 142621-02-1 N,N'-bis (3-trifluoromethylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine 
• 146-54-3 triflupromazine 
• 92-30-8 2-(trifluoromethyl)-10H-phenothiazine 
• 343-21-5 4-trifluoromethyl-10H-phenothiazine 
• 32086-01-4 C₁₄H₉ClF₃NO 
• 33414-30-1 BAS 01176608 
• 33414-29-8 10-(3-morpholin-4-yl-propionyl)-2-trifluoromethyl-10H-phenothiazine 
• 30223-48-4 Phthoracizin 

Relevant academic research and scientific papers

Facile synthesis of Fe@Pd nanowires and their catalytic activity in ligand-free CN bond formation in water

This work reports a facile synthesis of Fe@Pd nanowires. Ligand-free cross coupling reactions of arylboronic acids with various amines in aqueous medium proceed in very good to excellent yield with the use of Fe@Pd nanowires. Furthermore, the catalyst could be easily separated from the reaction mixture using a magnet and could be recycled several times without loss of catalytic activity.

Palladium-catalyzed amination of aryl sulfoxides

Amination of diaryl sulfoxides with anilines and alkylamines has been accomplished under palladium/N-heterocyclic carbene (NHC) catalysis. Owing to its electron deficiency, the leaving arenesulfenate anion would be smoothly released from the palladium center to result in uneventful catalyst turnover under milder reaction conditions in comparison with previous C-S bond amination reactions. This amination accommodated a wider range of functional groups such as silyl, boryl, methylsulfanyl, and halogen moieties. Regioselective amination of unsymmetrical diaryl sulfoxides was also executed by means of steric bias.

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).

Highly-chemoselective step-down reduction of carboxylic acids to aromatic hydrocarbons: Via palladium catalysis

Aryl carboxylic acids are among the most abundant substrates in chemical synthesis and represent a perfect example of a traceless directing group that is central to many processes in the preparation of pharmaceuticals, natural products and polymers. Herein, we describe a highly selective method for the direct step-down reduction of carboxylic acids to arenes, proceeding via well-defined Pd(0)/(ii) catalytic cycle. The method shows a remarkably broad substrate scope, enabling to direct the classical acyl reduction towards selective decarbonylation by a redox-neutral mechanism. The utility of this reaction is highlighted in the direct defunctionalization of pharmaceuticals and natural products, and further emphasized in a range of traceless processes using removable carboxylic acids under mild, redox-neutral conditions orthogonal to protodecarboxylation. Extensive DFT computations were conducted to demonstrate preferred selectivity for the reversible oxidative addition and indicated that a versatile hydrogen atom transfer (HAT) pathway is operable.

Copper-catalyzed, ceric ammonium nitrate mediated N-arylation of amines

Cu-Catalyzed, ligand- and base-free cross-coupling of aryl boronic acids with primary and secondary amines has been reported. This ‘Chan-Evans-Lam' reaction has revealed that at room temperature, with a catalytic amount of copper(ii) acetate and ceric ammonium nitrate (CAN) as an oxidant, N-arylation can result in an effective C-N bond formation. This air stable, practical, robust protocol enables tolerance towards a variety of functional groups on both boronic acid and amine partners.

Copper immobilized at a covalent organic framework: An efficient and recyclable heterogeneous catalyst for the Chan-Lam coupling reaction of aryl boronic acids and amines

A polyimide covalent organic framework (PI-COF) with high thermal and chemical stabilities has been readily prepared from commercially available and inexpensive reagents and was employed as an effective support for heterogeneous copper. It was demonstrated that the obtained Cu@PI-COF is a highly active heterogeneous catalyst which can effectively promote the Chan-Lam coupling reaction of aryl boronic acids and amines in an open flask without the aid of any base or additive. In addition, the catalyst could be readily recovered from the reaction mixture by simple filtration and reused for at least eight cycles without any observable change in structure and catalytic activity.

NIXANTPHOS: A highly active ligand for palladium catalyzed Buchwald-Hartwig amination of unactivated aryl chlorides

Xantphos is one of the two most common ligands used in palladium catalyzed Buchwald-Hartwig amination reactions, because of its broad scope and high probability of success. It does not, however, work well with unactivated aryl chlorides. Herein NIXANTPHOS is compared to Xantphos and an array of mono- and bidentate phosphines. NIXANTPHOS outperforms Xantphos and all other bidentate ligands examined. Under the optimal reaction conditions, unactivated aryl chlorides afford the expected products in good to excellent yield with as low as 0.05 mol% (500 ppm) palladium loading.

The first report on the preparation of peptide nanofibers decorated with zirconium oxide nanoparticles applied as versatile catalyst for the amination of aryl halides and synthesis of biaryl and symmetrical sulfides

We have reported the preparation of peptide nanofibers decorated with zirconium oxide nanoparticles for the first time as a novel, non-toxic, inexpensive and recyclable catalyst for the amination of aryl halides and synthesis of biaryl and symmetrical sulfides (via reaction of aryl halides with S8 or 2-thiobarbituric acid as sulfur transfer reagents). The structure of the catalyst was studied by Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), thermogravimetric analysis (TGA), atomic absorption spectroscopy (AAS), UV-visible absorption and fluorescence spectroscopy.

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.

Chan-Evans-Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem

The Chan-Evans-Lam reaction is a valuable C-N bond forming process. However, aryl boronic acid pinacol (BPin) ester reagents can be difficult coupling partners that often deliver low yields, in particular in reactions with aryl amines. Herein, we report effective reaction conditions for the Chan-Evans-Lam amination of aryl BPin with alkyl and aryl amines. A mixed MeCN/EtOH solvent system was found to enable effective C-N bond formation using aryl amines while EtOH is not required for the coupling of alkyl amines.