74447-72-6

Usage

Class

Aromatic organic compound

Structure

Biphenyl with a bromine atom and a methoxy group attached

Usage

Building block for constructing complex molecules in organic synthesis and chemical research

Applications

Development of pharmaceuticals, agrochemicals, and materials science

Utility

Versatile chemical with wide-ranging utility in organic chemistry

Potential

Serves as a starting material for the production of various organic compounds with specific functional groups or properties

Upstream product

• 108-86-1 bromobenzene 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 457-66-9 bis(4-methoxyphenyl)iodonium trifluoroacetate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 

Downstream Products

• 1358802-75-1 3-(2-hydroxyadamantan-2-yl)-4'-hydroxybiphenyl 
• 1358802-91-1 3-(2-methoxyadamantan-2-yl)-4'-hydroxybiphenyl 
• 1358802-87-5 3-(2-hydroxyadamantan-2-yl)-4'-methoxybiphenyl 

Relevant academic research and scientific papers

Platinum-catalyzed C-H arylation of simple arenes

This report describes the Na2PtCl4 catalyzed C-H arylation of arene substrates with diaryliodonium salts. The site selectivity of these reactions is predominantly controlled by steric factors. Remarkably, Na2PtCl4-catalyzed naphthalene arylation proceeds with opposite site selectivity compared to that obtained with Na2PdCl 4 as the catalyst. Preliminary mechanistic studies provide evidence for a PtII/PtIV catalytic cycle involving rate-limiting C-C bond-forming reductive elimination.

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.

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.

Generation of aryl radicals from arylboronic acids by manganese(III) acetate: Synthesis of biaryls and heterobiaryls

The efficient generation of aryl radicals from arylboronic acids by manganese(III) acetate is described. In aromatic solvents, in situ generated aryl radicals afford the corresponding biaryls in very good yields. This method works selectively, and yields

Manganese(III) acetate-mediated oxidative coupling of phenylhydrazines with benzene: A novel method for biaryl coupling

The reaction of phenylhydrazines with benzene in the presence of manganese(III) acetate affords biaryls in good yields. The same reaction was carried out with similar oxidants, such as CoIII, CeIV and PbIV; among these oxidants MnIII acetate shows higher efficiency and selectivity.