97067-18-0

Basic information

• Product Name: 4'-METHYL-4-TRIFLUOROMETHYL-BIPHENYL
• Synonyms: 4-METHYL-4'-(TRIFLUOROMETHYL)-1,1'-BIPHENYL;4'-METHYL-4-TRIFLUOROMETHYL-BIPHENYL;4-METHYL-4'-TRIFLUOROMETHYL-BIPHENYL;AKOS BAR-1096
• CAS NO: 97067-18-0
• Molecular Formula: C₁₄H₁₁F₃
• Molecular Weight: 236.23
• Mol File: 97067-18-0.mol

Chemical Properties

• Melting Point: 121.2-121.3 °C
• Boiling Point: 273.7±35.0 °C(Predicted)
• Appearance: /
• Density: 1.155±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 4'-METHYL-4-TRIFLUOROMETHYL-BIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-METHYL-4-TRIFLUOROMETHYL-BIPHENYL(97067-18-0)
• EPA Substance Registry System: 4'-METHYL-4-TRIFLUOROMETHYL-BIPHENYL(97067-18-0)

Safety Data

• Hazardous Substances Data: 97067-18-0(Hazardous Substances Data)

Upstream product

• 455-13-0 4-Iodobenzotrifluoride 
• 5142-75-6 tri(p-tolyl)bismuth 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 6952-59-6 3-cyanobromobenzene 
• 623-00-7 4-bromobenzenecarbonitrile 
• 106-38-7 para-bromotoluene 
• 1201594-37-7 (4-[trifluoromethyl]phenyl) N,N-dimethylsulfamate 
• 90252-89-4 p-tolylzinc(II) chloride 
• 5720-05-8 4-methylphenylboronic acid 
• 496922-59-9 N-benzyl-N-(1-octynyl)-p-toluenesulfonamide 
• 106-43-4 para-chlorotoluene 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 613-33-2 (4,4'-dimethyl-1,1'-biphenyl) 
• 613241-14-8 4-(bromomethyl)-4'-(trifluoromethyl)biphenyl 
• 1381958-89-9 4,4,5,5-tetramethyl-2-(4'-(trifluoromethyl)-[1,1^,-biphenyl]-4-yl)-1,3,2-dioxaborolane 

Relevant articles and documents

Palladium-Catalyzed Three-Component Coupling of Ynamides

A palladium-catalyzed regioselective three-component coupling of ynamides was developed. The reaction proceeded smoothly to furnish the desired products when carried out at 70 °C in acetonitrile/water with potassium carbonate in the presence of 2.5 mol percent Pd2(dba)3·CHCl3 without a ligand. Various iodides and boronic acids were used in this reaction, and a carbon-carbon bond was formed with satisfactory regioselectivity from the ynamides.

Precursors: Synthesis, Reactivity, and Catalytic Application to the Suzuki-Miyaura Reaction

The complexes (Cy2PC3H6PCy2)Ni(η2-arene) (arene = toluene (3), naphthalene (4)) have been synthesized and studied in detail. Displacement reactions of the toluene ligand afford the complexes (Cy2PC3H6PCy2)Ni(η2-styrene) (5), (Cy2PC3H6PCy2)Ni(PhCN) (6), (Cy2PC3H6PCy2)Ni(CO)2 (7), (Cy2PC3H6PCy2)Ni(PPh3) (8), (Cy2PC3H6PCy2)Ni(PCy3) (9), {(Cy2PC3H6PCy2)Ni}2(μ-H)2 (10), (Cy2PC3H6PCy2)Ni(η2-CO2) (11), and [(Cy2PC3H6PCy2)Ni]2(μ,η2-1,5-COD) (12). The relative rates of ArCl oxidative addition at Ni complexes 3, 4, 6, 8, and 12 have been evaluated experimentally, and the mechanism has been calculated by DFT. Complexes 3 and 4 are efficient catalysts for the Suzuki-Miyaura reaction between chloroarenes and Ar′B(OH)2.

Ruthenium-catalyzed oxidative homocoupling of arylboronic acids in water: Ligand tuned reactivity and mechanistic study

Molecular catalysts based on water-soluble arene-Ru(II) complexes ([Ru]-1-[Ru]-5) containing aniline (L1), 2-methylaniline (L2), 2,6-dimethylaniline (L3), 4-methylaniline (L4), and 4-chloroaniline (L5) were designed for the homocoupling of arylboronic acids in water. These complexes were fully characterized by 1H, 13C NMR, mass spectrometry, and elemental analyses. Structural geometry for two of the representative arene-Ru(II) complexes [Ru]-3 and [Ru]-4 was established by single-crystal X-ray diffraction studies. Our studies showed that the selectivity toward biaryls products is influenced by the position and the electronic behavior of various substituents of aniline ligand coordinated to ruthenium. Extensive investigations using 1H NMR, 19F NMR, and mass spectral studies provided insights into the mechanistic pathway of homocoupling of arylboronic acids, where the identification of important organometallic intermediates, such as σ-aryl/di(σ-aryl) coordinated arene-Ru(II) species, suggested that the reaction proceeds through the formation of crucial di(σ-aryl)-Ru intermediates by the interaction of arylboronic acid with Ru-catalyst to yield biaryl products.

Pincer-Nickel-Catalyzed Cross-Coupling of Aryl Sulfamates with Arylzinc Chlorides

The nickel N,N,N-pincer complex 2 was demonstrated to effectively catalyze the cross-coupling of aryl sulfamates with arylzinc chlorides under mild conditions. The reaction is suitable for a wide range of substrates, and tolerates various functional groups. A nickel N,N,N-pincer complex effectively catalyzes the cross-coupling of aryl sulfamates with arylzinc chlorides under mild conditions. The reaction is suitable for a wide range of substrates, and tolerates various functional groups.

Scope of the desulfinylative palladium-catalyzed cross-coupling of aryl sulfinates with aryl bromides

Herein is described the full scope of a desulfinylative cross-coupling of aryl sulfinates with aryl bromides. Optimized conditions were established and a bidentate phosphine ligand was found to be the key in obtaining good cross-coupling yields. Preliminary efforts to elucidate the reaction mechanism suggest that a Pd(0)-catalyzed mechanism is operative. Georg Thieme Verlag Stuttgart · New York.

Nickel/magnesium-lanthanum mixed oxide catalyst in the Kumada-coupling

A new, heterogeneous, magnesium-lanthanum mixed oxide solid base-supported nickel(ii) catalyst was developed. The catalyst was used successfully in the Kumada coupling of aryl halides, especially aryl bromides. The optimal reaction conditions of the coupling were determined.

Structure-reactivity relationships in negishi cross-coupling reactions

Competition experiments have been performed to determine the relative reactivities of substituted bromobenzenes and of different arylzinc reagents in the [Pd(PPh3)4]-catalyzed Negishi cross-coupling reaction in THF at 25 °C. The crosscoupling reactions are accelerated by electron acceptors in the bromobenzenes, the effect of which increases in the order ortho a larger effect than substituent variations in the arylzinc halides (ρ = -0.98).

A new palladium catalyzed protocol for atom-efficient cross-coupling reactions of?triarylbismuths with aryl halides and triflates

A new palladium catalyzed protocol for an atom-efficient cross-coupling reaction of triarylbismuths with aryl halides and triflates has been described. The palladium catalytic system with Cs2CO3 base was found to be very efficient in DMA solvent to furnish excellent yields of cross-coupled functionalized biaryls in short reaction times.