50670-49-0

Usage

Uses

4-Bromo-4'-methylbiphenyl is used as pharmaceutical intermediate.

Upstream product

• 201230-82-2 carbon monoxide 
• 5720-05-8 4-methylphenylboronic acid 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 92-86-4 4-(4-bromophenyl)bromobenzene 
• 74-88-4 methyl iodide 
• 589-87-7 1,4-bromoiodobenzene 
• 108-88-3 toluene 
• 108-86-1 bromobenzene 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 106-37-6 1.4-dibromobenzene 
• 149104-90-5 4-acetylphenylboronic acid 
• 18412-57-2 p-tolyltriethoxysilane 
• 624-31-7 4-tolyl iodide 
• 53034-21-2 α-(4-bromophenylazo)triphenylmethane 

Downstream Products

• 60916-53-2 Hydroxy-tris-(4'-methyl-biphenylyl-⁽⁴⁾)-methan 
• 50670-50-3 p-(p-tolyl)benzonitrile 
• 586-76-5 4-Bromobenzoic acid 
• 50670-57-0 4-bromo-4'-(bromomethyl)-1,1'-biphenyl 
• 117713-14-1 4-(but-3-en-1-yl)-4'-methyl-1,1'-biphenyl 
• 1381960-58-2 4,4,5,5-tetramethyl-2-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolane 
• 1204-78-0 4-(4-methylphenyl)aniline 
• 393870-04-7 (4'-methyl[1,1'-biphenyl]-4-yl)boronic acid 
• 644-08-6 4-Methylbiphenyl 
• 1351395-29-3 3-methyl-4,4-bis(4'-methylbiphenyl-4-yl)-N-(perfluorophenyl)but-3-enamide 

Relevant academic research and scientific papers

Copper catalysed Gomberg-Bachmann-Hey reactions of arenediazonium tetrafluoroborates and heteroarenediazonium o-benzenedisulfonimides. Synthetic and mechanistic aspects

Gomberg-Bachmann-Hey reactions were carried out in the presence of copper as a catalyst and gave rise to biaryls or heterobiaryls in good yields and in mild reaction conditions. A computational study of some key points of the reaction was performed. The results are coherent with the experimental data and confirm some aspects of the mechanism. The reaction free energies for the reduction in benzene by CuI of a set of 40 (hetero)arenediazonium tetrafluoroborates were calculated. Both the experiments and the calculations showed that in the coupling with substituted solvents (toluene, bromobenzene, nitrobenzene and anisole) the binding to the ortho position was always favoured.

Palladium (II)–Salan Complexes as Catalysts for Suzuki–Miyaura C–C Cross-Coupling in Water and Air. Effect of the Various Bridging Units within the Diamine Moieties on the Catalytic Performance

Water-soluble salan ligands were synthesized by hydrogenation and subsequent sulfonation of salens (N,N’-bis(slicylidene)ethylenediamine and analogues) with various bridging units (linkers) connecting the nitrogen atoms. Pd (II) complexes were obtained in reactions of sulfosalans and [PdCl4]2?. Characterization of the ligands and complexes included extensive X-ray diffraction studies, too. The Pd (II) complexes proved highly active catalysts of the Suzuki–Miyaura reaction of aryl halides and arylboronic acid derivatives at 80 ?C in water and air. A comparative study of the Pd (II)–sulfosalan catalysts showed that the catalytic activity largely increased with increasing linker length and with increasing steric congestion around the N donor atoms of the ligands; the highest specific activity was 40,000 (mol substrate) (mol catalyst × h)?1. The substrate scope was explored with the use of the two most active catalysts, containing 1,4-butylene and 1,2-diphenylethylene linkers, respectively.

Visible-Light-Promoted, Catalyst-Free Gomberg-Bachmann Reaction: Synthesis of Biaryls

Biaryls were synthesized via a novel visible-light-promoted Gomberg-Bachmann reaction that does not require a photosensitizer or any metal reagents. The formation of an electron donor-acceptor complex between aryl diazonium salts and pyridine allows, under visible-light irradiation, the synthesis of biaryls in moderate-to-high yields.

Synthesis, characterization, and nonlinear optical (NLO) properties of truxene-cored diphenylamine derivatives

Three star-shaped compounds based on a truxene core (FS11, FS12 and FS13) were prepared. The truxene core is incorporating with asymmetric diphenylamines, including one phenyl of diphenylamine substituted by methoxy group and the other phenyl substituted by tolyl, fluorophenyl and phenylethynyl for FS11, FS12 and FS13, respectively. Their one-photon, two-photon absorption, geometric structures, electrochemical behavior and thermal properties were investigated. The absorption maxima of charge transfer band for FS11, FS12 and FS13 are 375?nm, 373?nm and 383?nm, and the corresponding molar extinction coefficients of FS11, FS12 and FS13 is 79,950?M??1?cm??1, 67,220?M??1?cm??1 and 108,780?M??1?cm??1. The “pull-push” structure promotes charge transfer between asymmetric diphenylamine branches and the truxene core. Their two-photon absorbtion property is measured by two-photon induced fluorescence. The maximum two-photon cross-sections values of FS11, FS12 and FS13 are excited at 750?nm, which are 260 GM, 204GM and 367 GM, respectively.

Polymer biquinolyl-containing complexes of Pd(ii) as efficient catalysts for cyanation of aryl and vinyl halides with K4Fe(CN)6

A catalytic system for cyanation of aryl and vinyl halides with K4Fe(CN)6 based on a structurally tunable and nontoxic polymer backbone of polyamic type with biquinolyl fragments in the polymer chain capable of coordination to PdII ions is developed. The catalyst is eligible for thermal and microwave activation; in the latter case the reaction time is dramatically decreased. Cyanation of vinyl bromides occurs stereoselectively, and the configuration of the starting alkene is retained; even for Z-isomers the impact of configuration inversion is less than 5%. The polymer-based Pd catalyst is applicable for one-pot multi-step synthesis of the precursors of mesogenic structures of biphenyl type. Consecutive cross-coupling and cyanation reactions can be performed in the presence of the same portion of catalyst, in the same solvent, without isolation of intermediate products.

High Fluorescence Efficiencies and Large Stokes Shifts of Folded Fluorophores Consisting of a Pair of Alkenyl-Tethered, π-Stacked Oligo-p-phenylenes

A series of pure hydrocarbon fluorophores containing a pair of π-stacked oligo-p-phenylenes have been synthesized and analyzed by NMR and X-ray crystallography. They show good fluorescence in solutions and enhanced fluorescence in the aggregated state. Large Stokes shifts (up to 214 nm) have been achieved in these folded fluorophores in virtue of intramolecular energy transfer, and balanced structural rigidity and flexibility. These folded fluorophores provide perfect models for understanding the energy and charge transfer process in π-stacked systems.

C-Aryl glucoside SGLT2 inhibitors containing a biphenyl motif as potential anti-diabetic agents

A series of highly active C-aryl glucoside SGLT2 inhibitors containing a biphenyl motif were designed and synthesized for biological evaluation. Among the compounds tested, compound 16l demonstrated high inhibitory activity against SGLT2 (IC50 = 1.9 nM) with an excellent pharmacokinetic profile. Further study indicated that the in vivo efficacy of compound 16l was comparable to that of dapagliflozin, suggesting that further development would be worthwhile.

Palladium(II) complexes of 1,2,4-triazole-based N-heterocyclic carbenes: Synthesis, structure, and catalytic activity

Six palladium(II) complexes bearing three different triazole-based N-heterocyclic carbene (NHC) ligands, [1-tert-butyl-4-{2-[(N,N-dimethylamino) methyl]phenyl}-3-phenyl-1H-1,2,4-triazol-4-ium-5-ide, 1-tert-butyl-4-(2- methoxyphenyl)-3-phenyl-1H-1,2,4-triazol-4-ium-5-ide, and 1-tert-butyl-4-(4- methylphenyl)-3-phenyl-1H-1,2,4-triazol-4-ium-5-ide], were synthesized and fully characterized. NMR spectroscopy and X-ray diffraction analysis revealed that the amino-group-substituted NHC ligand is coordinated in bidentate fashion, forming a monocarbene chelate complex with an additional intramolecular Pd ← N bond with the nitrogen donor atom. The 4-methylphenyl- and 2-methoxyphenyl-substituted NHC ligands coordinate as C-monodentate donors, forming simple biscarbene Pd(II) complexes. The evaluation of the catalytic performance in the Suzuki-Miyaura cross-coupling reaction revealed very promising performance of the intramolecularly coordinated monocarbene complexes under relatively mild conditions even in direct comparison with the commercially available PEPPSI catalyst. In contrast, the biscarbene complexes proved inactive in this catalytic process. According to theoretical calculations (EDA and NOCV analysis), functionalization of the 1,2,4-triazole-based NHC with the 2-[(N,N-dimethylamino)methyl]phenyl group has a significant effect on the stability of the NHC-metal bond.

Copper-catalyzed cross-coupling of aryl- and heteroaryltriethoxysilanes with aryl and heteroaryl iodides and bromides

Copper(I)-catalyzed coupling of aryl- and heteroaryltriethoxysilanes with aryl and heteroaryl iodides is described. The transformation also proceeds with activated aryl bromides, but in this case it requires a stoichiometric amount of the catalyst for best product yields. The current reaction requires a P,N-based bidentate ligand for aryl-aryl coupling while it proceeds without external ligands for aryl-heteroaryl coupling to afford good product yields. The reaction protocol can also be applied to achieve biarylation of diiodoarenes in reasonable yields. Georg Thieme Verlag Stuttgart New York.

Pd/C-catalyzed cross-coupling of arenediazonium salts with potassium aryltrifluoroborates

A convenient protocol for the synthesis of biaryls from arenediazonium salts and potassium aryltrifluoroborates in refluxing methanol catalyzed by Pd/C is described. The protocol is simple to execute and gives moderate to high yields of cross-coupling products in most cases.