6242-98-4

Usage

Uses

Used in Pharmaceutical Industry:
4-BROMO-4'-NITROBIPHENYL is used as a building block for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique chemical structure allows for the creation of diverse organic compounds with potential medicinal properties.
Used in Agrochemical Industry:
In the agrochemical sector, 4-BROMO-4'-NITROBIPHENYL serves as an intermediate in the synthesis of various agrochemicals, including pesticides and herbicides. Its incorporation into these products aids in enhancing crop protection and yield.
Used in Dye and Pigment Production:
4-BROMO-4'-NITROBIPHENYL is utilized as an intermediate in the production of dyes and pigments, particularly for applications requiring specific color characteristics and stability. Its chemical properties enable the creation of a wide range of colorants for various industries, such as textiles, plastics, and printing inks.

Upstream product

• 92-93-3 1-phenyl-4-nitrobenzene 
• 7726-95-6 bromine 
• 7705-08-0 iron(III) chloride 
• 64-19-7 acetic acid 
• 7732-18-5 water 
• 540-80-7 tert.-butylnitrite 
• 109-63-7 boron trifluoride diethyl etherate 
• 5467-74-3 4-Bromophenylboronic acid 
• 100-01-6 4-nitro-aniline 
• 636-98-6 p-nitrobenzene iodide 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 98-95-3 nitrobenzene 
• 108-86-1 bromobenzene 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 

Downstream Products

• 586-76-5 4-Bromobenzoic acid 
• 62-23-7 4-nitro-benzoic acid 
• 38190-45-3 4-nitro-4''-amino-p-terphenyl 
• 92-93-3 1-phenyl-4-nitrobenzene 
• 69751-78-6 2-Amino-5-<4-brom-phenyl>-benzophenon 
• 69751-79-7 5-(4-bromo-phenyl)-3-phenyl-benzo[c]isoxazole 
• 881910-50-5 4''-ferrocenyl-4-nitro-1,1':4',1''-terphenyl 

Relevant academic research and scientific papers

Biaryl Coupling of Aryldiazonium Salts and Arylboronic Acids Catalysed by Gold

A gold-catalysed coupling of aryldiazonium salts with arylboronic acids is described. The reactions proceed in satisfactory yields under irradiation with blue LEDs in the presence of KF and a catalytic amount of ascorbic acid. Notably, 4-nitrobenzendiazonium tetrafluoroborate is sufficiently reactive to undergo the coupling with a variety of arylboronic acids in the absence of aryl radical initiators. The coupling is applicable for electron-donating and electron-withdrawing groups present at the para, ortho, and meta positions of both substrates.

Azo bond formation on metal surfaces

The formation of azo compounds via redox cross-coupling of nitroarenes and arylamines, challenging in solution phase chemistry, is achieved by on-surface chemistry. Reaction products are analyzed with a cryogenic scanning tunneling microscope (STM) and X-ray photoelectron spectroscopy (XPS). By using well-designed precursors containing both an amino and a nitro functionality, azo polymers are prepared on surface via highly efficient nitro-amino cross-coupling. Experiments conducted on other substrates and surface orientations reveal that the metal surface has a significant effect on the reaction efficiency. The reaction was further found to proceed from partially oxidized/reduced precursors in dimerization reactions, shedding light on the mechanism that was studied by DFT calculations.

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.

Modular and Selective Arylation of Aryl Germanes (C?GeEt3) over C?Bpin, C?SiR3 and Halogens Enabled by Light-Activated Gold Catalysis

Selective C (Formula presented.) –C (Formula presented.) couplings are powerful strategies for the rapid and programmable construction of bi- or multiaryls. To this end, the next frontier of synthetic modularity will likely arise from harnessing the coupling space that is orthogonal to the powerful Pd-catalyzed coupling regime. This report details the realization of this concept and presents the fully selective arylation of aryl germanes (which are inert under Pd0/PdII catalysis) in the presence of the valuable functionalities C?BPin, C?SiMe3, C?I, C?Br, C?Cl, which in turn offer versatile opportunities for diversification. The protocol makes use of visible light activation combined with gold catalysis, which facilitates the selective coupling of C?Ge with aryl diazonium salts. Contrary to previous light-/gold-catalyzed couplings of Ar–N2+, which were specialized in Ar–N2+ scope, we present conditions to efficiently couple electron-rich, electron-poor, heterocyclic and sterically hindered aryl diazonium salts. Our computational data suggest that while electron-poor Ar–N2+ salts are readily activated by gold under blue-light irradiation, there is a competing dissociative deactivation pathway for excited electron-rich Ar–N2+, which requires an alternative photo-redox approach to enable productive couplings.

Synthesis, characterization and catalytic performance of palladium supported on pyridine-based covalent organic polymer for Suzuki-Miyaura reaction

A bipyridine-based covalent organic polymer (COP) was successfully synthesized by condensation of trimesoyl chloride (TMC) and 2,2′-bipyridine-5,5′-diamine (Bpy) under ambient conditions. This material was modified by coordination of PdCl2 to COP framework, affording a hybrid material, Pd@TMC-Bpy COP, which was applied as a highly efficient heterogeneous catalyst for Suzuki-Miyaura reaction under ligand-free conditions in ethyl lactate. The catalyst could be reused for five times without obvious loss of its activity.

Gold catalysed Suzuki-Miyaura coupling of arenediazonium o-benzenedisulfonimides

Arenediazonium o-benzenedisulfonimides have been used as efficient electrophilic partners in Au(I) catalysed Suzuki coupling reactions. The synthetic protocol is general, easy and produced either biaryls or heteroaryl arenes in good yields (51 positive examples, average yield 80%). o-Benzenedisulfonimide was recovered at the end of the reactions and was reused to prepare the starting salts for further reactions. Mechanistic insights suggest that the o-benzenedisulfonimide anion act as an electron transfer agent and promotes a catalytic cycle which does not require the presence of photocatalysts or external oxidants.

Ni(II) catalyzed bromination of aryl C-H bonds

Bromination of unactivated aromatic C-H bonds without directing and/or chelating groups was achieved by employing an air stable N-heterocyclic Ni(II) complex. PhI(OAC)2 and N-bromosuccinimide have been used as the oxidizing agent and the bromin

Ni(II) catalyzed bromination of aryl C-H bonds

Bromination of unactivated aromatic C-H bonds without directing and/or chelating groups was achieved by employing an air stable N-heterocyclic Ni(II) complex. PhI(OAC)2and N-bromosuccinimide have been used as the oxidizing agent and the bromine source, respectively. Yields for bromination are as high as >99%, especially in presence of electron-withdrawing groups like -NO2and -CF3. This is a rare report on C-H bond activation with Ni(II) where, instead of homo C-C coupling, reductive elimination to form C-halogen could be achieved.

Selective Suzuki-Miyaura monocouplings with symmetrical dibromoarenes and aryl ditriflates for the one-pot synthesis of unsymmetrical triaryls

The various parameters that would permit selective Suzuki-Miyaura monocouplings of symmetrical dihaloarenes were studied. High selectivity and efficiency can be obtained for a broad range of substrates by using operationally simple conditions and widely available reagents. The 38 different examples described provide a valuable toolbox for the rapid access to unsymmetrical triaryls, as illustrated by the preparation of diarylpyridine 8, terphenyl 9, and diarylpyrrole 10. By studying several key parameters, the factors that allow selective Suzuki-Miyaura monocoupling of symmetrical dihaloarenes have been outlined. This study serves as the basis for the efficient synthesis of unsymmetrical triaryls from symmetrical dibromoarenes and aryl ditriflates by a one-pot desymmetrizing double Suzuki-Miyaura coupling. Copyright

Single and double Suzuki-Miyaura couplings with symmetric dihalobenzenes

(Chemical Equation Presented) m- or p-diiodobenzene undergoes selective double coupling reactions with arylboronic acids and esters. Selectivity for double coupling over single coupling is remarkably strong: even with a diiodobenzene:monoboronic acid ratio of 10:1, the products of double coupling are formed in good yields. Steric hindrance and electronic influences of the boronic acid or ester, and reaction conditions do not appear to impact significantly upon the outcome of the reaction. In contrast, m- and p-dibromobenzenes undergo single couplings with aryl boronic acids with high selectivity.