1601-98-5

Usage

Uses

Used in Pharmaceutical Industry:
1,2-Bis(4-bromophenyl)diazene is used as a chemical intermediate for the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique structure and reactivity allow for the creation of diverse molecular entities with potential medicinal properties.
Used in Agrochemical Industry:
In the agrochemical sector, 1,2-Bis(4-bromophenyl)diazene serves as a precursor in the production of various agrochemicals, such as pesticides and herbicides. Its involvement in the synthesis of these compounds helps address challenges in crop protection and agricultural management.
Used in Materials Science:
1,2-Bis(4-bromophenyl)diazene is utilized as a building block in the development of advanced materials with specific properties for applications in materials science. Its chemical versatility enables the creation of materials with tailored characteristics for use in various industries, including electronics, coatings, and polymers.
It is crucial to handle 1,2-Bis(4-bromophenyl)diazene with care, as it may pose hazards if not used properly, ensuring safety in research, development, and industrial applications.

InChI:InChI=1/C12H8Br2N2/c13-9-1-5-11(6-2-9)15-16-12-7-3-10(14)4-8-12/h1-8H/b16-15+

Upstream product

• 17333-82-3 4-bromo-benzenediazonium ion 
• 586-78-7 para-nitrophenyl bromide 
• 106-50-3 1,4-phenylenediamine 
• 19717-43-2 4,4'-dibromo-N,N'-diphenylhydrazine 
• 1227476-15-4 Azobenzene 
• 4418-84-2 4-bromoazobenzene 
• 106-40-1 4-bromo-aniline 
• 110-86-1 pyridine 
• 72437-42-4 [(4-bromophenyl)diazenyl](phenyl)methyl hydroperoxide 
• 5194-50-3 (E,Z)-2,4-hexadiene 
• 118622-96-1 N-(4-bromophenylaminothio)phthalimide 
• 2101-88-4 1-azido-4-bromobenzene 
• 131367-95-8 1,3-bis(p-bromophenyl)-2,4-bis(o-methoxyphenyl)-1,3,2,4-diazadiarsetidine 
• 1215-42-5 4,4'-dibromoazoxybenzene 

Downstream Products

• 19717-43-2 4,4'-dibromo-N,N'-diphenylhydrazine 
• 1215-42-5 4,4'-dibromoazoxybenzene 
• 111122-29-3 1,2-Bis-(4-bromo-phenyl)-tetrahydro-pyridazine-3,6-dione 
• 106-40-1 4-bromo-aniline 
• 148-85-6 4,4'-bis(4-carboxyphenyl)azobenzene 
• 81701-88-4 5-bromo-2-(4-bromophenylazo)phenol 
• 38224-46-3 5-bromo-2-(4-bromophenyl)-2H-benzo[d][1,2,3]triazole 
• 7702-38-7 N-(4-bromophenyl)benzamide 
• 2491-52-3 4-nitroazobenzene 

Relevant academic research and scientific papers

Catalytic oxidation of primary aromatic amines with sodium periodate catalyzed by Mn(III)salophen complex supported on polystyrene-bound imidazole

The catalytic activity of Mn(III)salophen complex supported on polystyrene-bound imidazole, [Mn(salophen)Cl-PSI], was studied in the oxidation of primary aromatic amines in acetonitrile/water, using sodium periodate as an oxygen source. Amines were oxidized efficiently to their corresponding azo derivatives in the presence of this catalyst. The heterogeneous catalyst showed high stability and reusability in the oxidation reactions and could be reused several times without loss of its activity. The effect of different solvents was studied in the oxidation of p-toluidine and CH3CN/H2O was chosen as the solvent.

Cytochrome P-450 dependent monooxygenases model system: Rapid and efficient oxidation of primary aromatic amines to azo derivatives with sodium periodate catalyzed by manganese(III) Schiff base complexes

Rapid and efficient oxidation of primary aromatic amines was investigated. Mn(III)-salophen catalyst can catalyze the oxidation of primary aromatic amines to azo derivatives with sodium periodate. The ability of various Schiff base complexes in this oxidation system was also investigated.

Formal [4+2] cycloaddition of 3-ethoxycyclobutanones with azo compounds

Azobenzenes reacted with 3-ethoxycyclobutanoes to give 2,3-dihydro-pyridazin-4(1H)-ones by using EtAlCl2as a Lewis acid. Thus, ring cleavage of 3-ethoxycyclobutanones took place to form a zwitterionic intermediate by activation with EtAlCl2, and intermolecular formal [4+2] cycloaddition of the zwitterionic intermediate proceeded with azobenzenes to give 2,3-dihydro-pyridazin-4(1H)-ones after elimination of ethanol. Regioselectivity for cycloaddition of unsymmetrical azobenzenes, ring contraction and chemoselective reduction of 2,3-dihydro-pyridazin-4(1H)-ones, and [4+2] cycloaddition to 4-phenyl-1,2,4-triazolin-3,5-dione are also described.

Synthesis, characterization and photophysical studies of self-assembled azo biphenyl urea derivatives

We reported the synthesis of a new series of azobiphenyl based urea derivatives 7 and their stimulus-responsive supramolecular structures in the form of sheet like self-assembled formations. The self-assembled nanostructural formations of azo derivatives

Continuous and green microflow synthesis of azobenzene compounds catalyzed by consecutively prepared tetrahedron CuBr

An environmentally friendly and cross-selective process intensification for the continuous synthesis of symmetric aromatic azo compounds by using self-made cuprous bromide as the catalyst under mild conditions in the microreactor was developed. A novel tetrahedron cuprous bromide catalyst which shows outstanding catalytic activity and satisfactory stability has been synthesized in continuous flow microreactor. The online immobilization of self-made cuprous bromide on the catalyst bed achieved oxidative coupling of aromatic amines (oxygen as oxidant) and high-performance gas–liquid–solid three-phase reaction, which strongly limited the possibility of undesired reaction pathways, improving product selectivity and reducing waste generation. Meanwhile, the yield of azo-coupling reaction was up to 98% under optimized condition. As compared with earlier traditional method (diazotization reaction) for synthesizing azobenzene, the designed micro-flow process displays signi?cant advances in terms of selectivity, waste emissions, sustainability and productivity. The combination of online immobilization of self-made cuprous bromide and precise and safe control through the microreactor provides a green solution for the industrial production of valuable aromatic azo compounds.

Aerobic Oxidative coupling of aniline catalyzed by one-dimensional manganese hydroxide nanomaterials

The aerobic oxidative coupling of aniline is an effective process for producing aromatic azo compounds, which are widely used in the organic chemical industry. The development of heterogeneous catalysts for this reaction would be advantageous because of their recyclability and convenience in posttreatment. In this work, one-dimensional Mn(OH) 2 nanostructure with various shapes were synthesized through the adjustment of various surfactants. The as-synthesized Mn(OH) 2 nanobelts and nanowires showed superior catalytic activity in the activation of oxygen and aniline. Aromatic azo compounds with a variety of substituents were produced through the coupling of the corresponding anilines without additives under ambient conditions.

Efficient Catalytic Oxidation of Primary Aromatic Amines to Azo Derivatives by Manganese(III) Tetraphenylporphyrin

The oxidation of primary aromatic amines to the corresponding azo derivatives has been observed in catalytic systems containing manganese(III) tetraphenylporphyrin and sodium periodate in the presence of heterocyclic nitrogen bases acting as axial ligands.

Correlation studies in the oxidation of Vanillin Schiff bases by acid bromate - A kinetic and semi-empirical approach

Kinetics and mechanistic aspects of oxidation of Vanillin Schiff bases (obtained from Vanillin and p-substituted anilines) by bromate in acid medium has been studied at 313 ?K. The reaction exhibited first order in [bromate] and less than unity order each in [Vanillin Schiff base] and [acid]. The increase in the rate of reaction with decrease in dielectric constant of the medium is observed with all the studied substrates. The reaction failed to induce the polymerization of acrylonitrile. Electron withdrawing substituents in the aniline ring moiety of Vanillin Schiff base accelerate the rate of oxidation to a large extent and electron releasing substituents retard the rate. The order of reactivity is found to be p-nitro ?> ?p-bromo ?> ?p-chloro ?> ?–H ?> ?p-fluoro ?> ?p-methyl ?> ?p-methoxy ?> ?p-ethoxy and the sensitivity of the substrates towards the reaction rate is further supported by the semi-empirical calculation of electronic properties and global descriptors of the substrates (Vanillin Schiff bases) with different substituents in the aniline ring moiety. The observed trend in the reactivity of the substrates was correlated with the calculated descriptors like electronegativity, chemical potential, electrophilicity index, chemical hardness and frontier molecular orbitals. The linear free-energy relationship is characterized by a straight line in the Hammett's plot of log k versus σ. The ρ values are positive and increase with increase in temperature. From the Exner and Arrhenius plots, the isokinetic relationship is discussed. Oxidation products identified are p-substituted azobenzene and vanillic acid. Based on the experimental observations, a plausible mechanism is proposed and rate law is derived.

Electrosynthesis of Azobenzenes Directly from Nitrobenzenes

The electrochemical reduction strategy of nitrobenzenes is developed. The chemistry occurs under ambient conditions. The protocol uses inert electrodes and the solvent, DMSO, plays a dual role as a reducing agent. Its synthetic value has been demonstrated by the highly efficient synthesis of symmetric, unsymmetric and cyclic azo compounds.

Metal- and oxidant-free electrochemically promoted oxidative coupling of amines

The selective oxidation of amines into imines is a priority research topic in organic synthesis and has attracted much attention over the past few decades. However, the oxidation of amines generally suffers from the drawback of transition-metal, even noble-metal catalysts. Thus, the strategy of metal- and oxidant-free selective synthesis of imines is highly desirable yet largely unmet. This paper unravels a metal-free and external oxidant-free electrochemical strategy for the oxidative coupling methodology of amines. This general transformation is compatible with various functional amines and led to functionalized imines in moderate to satisfactory yields.