398-36-7

Usage

Uses

Used in Pharmaceutical Industry:
4-(TRIFLUOROMETHYL)-BIPHENYL is used as a building block for the synthesis of various pharmaceuticals due to its unique chemical properties and stability, contributing to the development of new drugs with improved efficacy and safety profiles.
Used in Agrochemical Industry:
In the agrochemical sector, 4-(TRIFLUOROMETHYL)-BIPHENYL is utilized as a key component in the creation of agrochemicals, enhancing their performance and stability, which is crucial for effective pest control and crop protection.
Used in Organic Materials Synthesis:
4-(TRIFLUOROMETHYL)-BIPHENYL is employed as a precursor in the synthesis of organic materials, where its trifluoromethyl group imparts specific properties that are beneficial for the development of advanced materials with tailored characteristics for various applications.

InChI:InChI=1/C13H9F3/c14-13(15,16)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H

Upstream product

• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 185515-88-2 hexakis[4-(trifluoromethyl)phenyl]tellurium 
• 841-76-9 triphenylaluminium 
• 98-56-6 4-chlorobenzotrifluoride 
• 108-86-1 bromobenzene 
• 21856-96-2 Diphenyl<4-(trifluormethyl)phenyl>methanol 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 100-59-4 phenylmagnesium chloride 
• 38111-44-3 phenylzinc(II) bromide 
• 98-80-6 phenylboronic acid 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 455-13-0 4-Iodobenzotrifluoride 
• 603-33-8 triphenylbismuthane 
• 201230-82-2 carbon monoxide 

Downstream Products

• 80245-34-7 4-nitro-4’-(trifluoromethyl)biphenyl 
• 644-08-6 4-Methylbiphenyl 
• 92-89-7 4'-nitro-biphenyl-4-carboxylic acid 
• 1625-92-9 4-tert-butylbiphenyl 
• 255837-15-1 2-bromo-4’-trifluoromethyl-1,1’-biphenyl 
• 69231-87-4 4-bromo-4'-(trifluoromethyl)-1,1'-biphenyl 
• 420-56-4 trimethylsilyl fluoride 
• 30203-93-1 4-[(4-methylphenyl)methyl]-1,1’-biphenyl 
• 613-42-3 4-benzylbiphenyl 
• 102683-23-8 2-([1,1'-biphenyl]-4-ylmethyl)naphthalene 
• 1049014-97-2 4-(2,5-dimethylbenzyl)-1,1'-biphenyl 

Relevant academic research and scientific papers

Synthesis, structures and catalytic activity of cyclometalated rhenium complexes

Thermal reactions of aryl-substituted phosphines or phosphinites with Re2(CO)10 in chlorobenzene resulted in the corresponding five-membered cyclometalated rhenium complexes (1-5) via an intramolecular activation of the C(sp2)-H or C(sp3)-H bond. The only exception occurred in the case of (1-naphthyl)diisopropylphosphinite, which gave a diphosphinite-substituted dinuclear rhenium complex 6. Competition reaction indicated that the aromatic C(sp2)-H bond is more likely to be activated than the C(sp3)-H bond under the same conditions. Photolysis of 1 or 2 in CHX3 led to the cleavage of the Re-C σ bond to yield corresponding phosphine-substituted tetracarbonyl rhenium halides 7-10. Complex 1 reacted with CF3COOH in CH2Cl2 to give addition product 11. Photolysis of cyclorhenated complexes 1-3 with a series of aryl halides in benzene resulted in the stoichiometric formation of biphenyl, together with corresponding phosphine-substituted tetracarbonyl rhenium halides (7, 9, 10, 12, and 13). When base was introduced into the above reaction, a catalytic system was established. Under optimized conditions, complex 1 provided moderate yield of biphenyl in a couple of hours at a [Re] : substrate ratio of 1 : 200. Molecular structures of complexes 1, 6, 9, and 11 were determined by X-ray diffraction.

Cobalt-catalyzed cross-coupling reactions of aryl- And alkylaluminum derivatives with (hetero)aryl and alkyl bromides

A simple cobalt complex, such as Co(phen)Cl2, turned out to be a highly efficient and cheap precatalyst for a host of cross-coupling reactions involving aromatic and aliphatic organoaluminum reagents with aryl, heteroaryl and alkyl bromides. New C(sp2)-C(sp2) and C(sp2)-C(sp3) bonds were formed in good to excellent yields and with high chemoselectivity, under mild reaction conditions.

Synthesis of biaryl ketones and biaryl diketones via carbonylative Suzuki-Miyaura coupling reactions catalyzed by bridged bis(N-heterocyclic carbene)palladium(II) catalysts

This disclosure relates to bridged bis(N-heterocyclic carbene)palladium(II) complexes, methods of preparing the complexes, and methods of using the complexes in Suzuki-Miyaura coupling reactions.

Cobalt-catalyzed C(sp2)?CN bond activation: Cross-electrophile coupling for biaryl formation and mechanistic insight

Herein, we report a cross-electrophile coupling of benzonitrile derivatives and aryl halides with a simple cobalt-based catalytic system under mild conditions to form biaryl compounds. Even though the cobalt catalyst is able to activate the C(sp2)?CN bond alone, the use of the AlMe3 Lewis acid enhances the reactivity of benzonitriles and improves the cross-selectivity with barely any influence on the functional group compatibility. X-ray structure determination of an original low-valent cobalt species combined with catalytic and stoichiometric reactions reveals a catalytically active cobalt(I) species toward the aryl halide partner. On the other hand, experimental insights, including cyclic voltammetry experiments, suggest the involvement of a cobalt complex of a lower oxidation state to activate the benzonitrile derivative. Finally, density functional theory calculations support the proposed mechanistic cycle involving two low-valent cobalt species of different oxidation states to perform the reaction.

Transition-Metal-Free Oxidative Cross-Coupling of Tetraarylborates to Biaryls Using Organic Oxidants

Readily prepared tetraarylborates undergo selective (cross)-coupling through oxidation with Bobbitt's salt to give symmetric and unsymmetric biaryls. The organic oxoammonium salt can be used either as a stoichiometric oxidant or as a catalyst in combination with in situ generated NO2 and molecular oxygen as the terminal oxidant. For selected cases, oxidative coupling is also possible with NO2/O2 without any additional nitroxide-based cocatalyst. Transition-metal-free catalytic oxidative ligand cross-coupling of tetraarylborates is unprecedented and the introduced method provides access to various biaryl and heterobiaryl systems.

Novel and efficient bridged bis(N-heterocyclic carbene)palladium(II) catalysts for selective carbonylative Suzuki–Miyaura coupling reactions to biaryl ketones and biaryl diketones

Bridged N,N′-substituted bisbenzimidazolium bromide salts (L1, L2, and L3) were synthesized and fully characterized. Reactions of palladium acetate with L1, L2, and L3 afforded corresponding new bridged bis(N-heterocyclic carbene)palladium(II) complexes (C1, C2, and C3) in high yields. The X-ray structure of complex C1 showed that the Pd(II) ion is bonded to the two carbon atoms of the bis(N-heterocyclic carbene) and two bromido ligands are in the cis position, resulting in a distorted square planar geometry. The three Pd(NHC)2Br2 complexes C1, C2, and C3 were evaluated in carbonylative Suzuki–Miyaura coupling reactions of aryl boronic acids with aryl halides and displayed high catalytic activity with low catalyst loading. The coupling reactions of aryl bromides were selective towards the carbonylation product at higher carbon monoxide pressure.

Binuclear Palladium Complex Immobilized on Mesoporous SBA-16: Efficient Heterogeneous Catalyst for the Carbonylative Suzuki Coupling Reaction of Aryl Iodides and Arylboronic Acids Using Cr(CO)6 as Carbonyl Source

Abstract: In this study, a binuclear palladium complex immobilized on the organo-functionalized SBA-16 was prepared and structurally characterized by routine techniques. Characterizations indicated that the mesostructure of SBA-16 was maintained after the immobilization of palladium complex. Then, the prepared nanomaterial was applied as a heterogeneous catalyst in the carbonylative Suzuki coupling reaction of aryl iodides with arylboronic acids using Cr(CO)6 as carbonyl source. The catalyst was efficiently promoted the coupling reactions of various aryl iodides and arylboronic acids to give the corresponding diaryl ketones in excellent yields. Moreover, the catalyst was readily recovered by filtration and could be reused for seven cycles without losing its structural integrity and catalytic activity. Graphic Abstract: [Figure not available: see fulltext.].

Cu-Mediated arylselenylation of aryl halides with trifluoromethyl aryl selenonium ylides

An unprecedented arylselenylation of aryl halides with trifluoromethyl aryl selenonium ylides in the presence of copper is described. The reaction proceeded at 100-140 °C under ligand- and additive-free conditions for 3-20 h to form a variety of unsymmetrical diaryl selenides in good to high yields. Arylselenylation is easy to operate, has good functional group tolerance, and demonstrates the different reaction profiles of trifluoromethyl aryl selenonium ylides from the homologous trifluoromethyl aryl sulfonium ylides.

Palladium nanocatalysts in glycerol: Tuning the reactivity by effect of the stabilizer

Palladium nanoparticles (PdNPs) prepared in neat glycerol containing TPPTS (tris(3-sulfophenyl)phosphine trisodium salt) or cinchona-based alkaloids (cinchonidine, quinidine) as capping agents, were applied as catalysts in fluoride-free Hiyama couplings and conjugate additions with the aim of evaluating the influence of the stabilizer in the catalytic reactivity. Therefore, PdNPs stabilized by phosphine favored C–C cross-couplings, whereas those containing alkaloids showed enhanced suitability for C–C homo-couplings and conjugate additions. The metal/stabilizer coordination mode, i.e. Pd–P dative bond and π-π interaction between quinoline moiety and palladium surface, is certainly key for the stabilization of different active metallic species and then promoting distinctive catalytic pathways.

Facile routes to abnormal-NHC-cobalt(II) complexes

Deprotonation of [IPrPh]I (1) with Co{N(SiMe3)2}2 readily affords the abnormal N-heterocyclic carbene (aNHC) complex (aIPrPh)2CoI2 (2) (aIPrPh = 1,3-bis(2,6-iPr2C6H3)-2-phenyl-imidazol-4-ylidene). Treatment of 1 with NaHBEt3 yields (aIPrPh)BEt3 (3) that serves as an aNHC-transfer agent and yields (aIPrPh)Co{N(SiMe3)2}2 (4) on reaction with Co{N(SiMe3)2}2.