1215-42-5

Usage

Uses

Used in Organic Synthesis:
4,4'-DIBROMOAZOXYBENZENE is used as a reagent in organic synthesis for the preparation of various organic compounds. Its unique chemical properties make it a valuable component in the synthesis of a wide range of products.
Used in Azo Dyes and Pigments Production:
In the dye and pigment industry, 4,4'-DIBROMOAZOXYBENZENE is used as a key intermediate in the production of azo dyes and pigments. These dyes and pigments are widely used in various applications, such as textiles, plastics, and printing inks, due to their vibrant colors and stability.
Used as a Pharmaceutical Intermediate:
4,4'-DIBROMOAZOXYBENZENE also finds application in the pharmaceutical industry as an intermediate in the synthesis of various drugs. Its unique structure allows for the development of new and innovative pharmaceutical compounds.
However, it is important to note that 4,4'-DIBROMOAZOXYBENZENE has been classified as a mutagen, posing potential health and environmental hazards. Therefore, it is crucial to handle and store this chemical compound with caution and in compliance with safety regulations to minimize any risks associated with its use.

InChI:InChI=1/C12H8Br2N2O/c13-9-1-5-11(6-2-9)15-16(17)12-7-3-10(14)4-8-12/h1-8H/b16-15-

Upstream product

• 64-17-5 ethanol 
• 10468-46-9 N-(4-bromophenyl)hydroxylamine 
• 586-96-9 Nitrosobenzene 
• 2372-45-4 sodium butanolate 
• 586-78-7 para-nitrophenyl bromide 
• 71-43-2 benzene 
• 16109-68-5 4-bromo-1-phenyl-NNO-azoxybenzene 
• 6831-82-9 potassium isopropoxide 
• 95-20-5 2-methyl-1H-indole 
• 3623-23-2 4-bromonitrosobenzene 
• 3463-40-9 2,4,6-tribromonitrobenzene 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 64-19-7 acetic acid 

Downstream Products

• 1601-98-5 (E)-bis(4-bromophenyl)diazene 
• 81701-88-4 5-bromo-2-(4-bromophenylazo)phenol 
• 81701-91-9 C₁₂H₈Br₂N₂O 
• 1601-98-5 1,2-bis(4-bromophenyl)diazene 
• 3035-94-7 4-((p-bromophenyl)diazenyl)phenol 
• 19717-43-2 4,4'-dibromo-N,N'-diphenylhydrazine 
• 21865-50-9 6-bromo-1,2,3,4-tetrahydro-9H-carbazole 

Relevant academic research and scientific papers

Efficient Solar-Driven Hydrogen Transfer by Bismuth-Based Photocatalyst with Engineered Basic Sites

Photocatalytic organic conversions involving a hydrogen transfer (HT) step have attracted much attention, but the efficiency and selectivity under visible light irradiation still needs to be significantly enhanced. Here we have developed a noble metal-free, basic-site engineered bismuth oxybromide [Bi24O31Br10(OH)] that can accelerate the photocatalytic HT step in both reduction and oxidation reactions, i.e., nitrobenzene to azo/azoxybenzene, quinones to quinols, thiones to thiols, and alcohols to ketones under visible light irradiation and ambient conditions. Remarkably, quantum efficiencies of 42% and 32% for the nitrobenzene reduction can be reached under 410 and 450 nm irradiation, respectively. The Bi24O31Br10(OH) photocatalyst also exhibits excellent performance in up-scaling and stability under visible light and even solar irradiation, revealing economic potential for industrial applications.

Selective oxidation of primary substituted aromatic amines to azoxy products using lacunary catalyses

Some of the substituted anilines were selectively converted in to the corresponding azoxy and azobenzenes by oxidation with 30% aqueous hydrogen peroxide. The reactions were catalyzed by various heteropolyoxometalates, at boiling point of the used solvent

Cadmium chloride-zinc catalysed selective reduction of nitro aromatics to azoxy compounds

Treatment of aromatic nitro compounds with cadmium chloride-metallic zinc combination systems has been shown to display a good reaction selectivity in the formation of symmetrical azoxy compounds in high yields.

Zr(OH)4-Catalyzed Controllable Selective Oxidation of Anilines to Azoxybenzenes, Azobenzenes and Nitrosobenzenes

The selective oxidation of aniline to metastable and valuable azoxybenzene, azobenzene or nitrosobenzene has important practical significance in organic synthesis. However, uncontrollable selectivity and laborious synthesis of the expensive required catalysts severely hinders the uptake of these reactions in industrial settings. Herein, we have pioneered the discovery of Zr(OH)4 as an efficient heterogeneous catalyst capable of the selective oxidation of aniline, using either peroxide or O2 as oxidant, to selectively obtain various azoxybenzenes, symmetric/unsymmetric azobenzenes, as well as nitrosobenzenes, by simply regulating the reaction solvent, without the need for additives. Mechanistic experiments and DFT calculations demonstrate that the activation of H2O2 and O2 is primarily achieved by the bridging hydroxyl and terminal hydroxyl groups of Zr(OH)4, respectively. The present work provides an economical and environmentally friendly strategy for the selective oxidation of aniline in industrial applications.

Convergent Paired Electrochemical Synthesis of Azoxy and Azo Compounds: An Insight into the Reaction Mechanism

A convergent paired electrochemical method was developed for the synthesis of azoxy and azo compounds starting from the corresponding nitroarenes. We propose a unique mechanism for electrosynthesis of azoxy and azo compounds. We find that both anodic and cathodic reactions are responsible for the synthesis of these compounds. The synthesis of azoxy and azo derivatives have been successfully performed in an undivided cell, using carbon rod electrodes, by constant current electrolysis at room temperature.

Continuous Flow Synthesis of Azoxybenzenes by Reductive Dimerization of Nitrosobenzenes with Gel-Bound Catalysts

In the search for a new synthetic pathway for azoxybenzenes with different substitution patterns, an approach using a microfluidic reactor with gel-bound proline organocatalysts under continuous flow is presented. Herein the formation of differently substituted azoxybezenes by reductive dimerization of nitrosobenzenes within minutes at mild conditions in good to almost quantitative yields is described. The conversion within the microfluidic reactor is analyzed and used for optimizing and validating different parameters. The effects of the different functionalities on conversion, yield, and reaction times are analyzed in detail by NMR. The applicability of this reductive dimerization is demonstrated for a wide range of differently substituted nitrosobenzenes. The effects of these different functionalities on the structure of the obtained azoxyarenes are analyzed in detail by NMR and single-crystal X-ray diffraction. Based on these results, the turnover number and the turnover frequency were determined.

SO2F2-mediated oxidation of primary and tertiary amines with 30% aqueous H2O2 solution

A highly efficient and selective oxidation of primary and tertiary amines employing SO2F2/H2O2/base system was described. Anilines were converted to the corresponding azoxybenzenes, while primary benzylamines were transformed into nitriles and secondary benzylamines were rearranged to amides. For tertiary amine substrates quinolines, isoquinolines and pyridines, their oxidation products were the corresponding N-oxides. The reaction conditions are very mild and just involve SO2F2, amines, 30% aqueous H2O2 solution, and inorganic base at room temperature. One unique advantage is that this oxidation system is just composed of inexpensive inorganic compounds without the use of any metal and organic compounds.

Selective Oxidation of Anilines to Azobenzenes and Azoxybenzenes by a Molecular Mo Oxide Catalyst

Aromatic azo compounds, which play an important role in pharmaceutical and industrial applications, still face great challenges in synthesis. Herein, we report a molybdenum oxide compound, [N(C4H9)4]2[Mo6O19] (1), catalyzed selective oxidation of anilines with hydrogen peroxide as green oxidant. The oxidation of anilines can be realized in a fully selectively fashion to afford various symmetric/asymmetric azobenzene and azoxybenzene compounds, respectively, by changing additive and solvent, avoiding the use of stoichiometric metal oxidants. Preliminary mechanistic investigations suggest the intermediacy of highly active reactive and elusive Mo imido complexes.

Shape-dependent reactivity and chemoselectivity of nanogold towards nitrophenol reduction in water

Although the catalytic activity of nano-gold surfaces for the reduction of nitro compounds has been known, the effect of their shape has been rarely evaluated. Here, the synthesis, characterization, and application of both gold nanoworms (GNW) and gold nanospheres (GNS) are described. Both GNW and GNS were characterized using SEM, TEM, UV–Vis, FTIR, and XPS spectroscopy. The catalytic efficiency of GNW with an average dimensions of 2 × 250 nm (D × L) towards the hydrogenation of nitrophenol, a pollutant present in industrial wastewater, is higher (TOF 3675 h?1) than that of spherical GNS (10 ± 1 nm), for which TOF is 1838 h?1 in water using NaBH4 as the reductant. The selectivity of 4-aminophenol is 100% for both GNS and GNW.

Palladium Nanoparticles on Silica Nanospheres for Switchable Reductive Coupling of Nitroarenes

Abstract: In this study, we synthesized a robust and sustainable Pd/SiO2 nanospheres catalyst. Further, its catalytic activity was demonstrated for the direct reductive coupling of nitroarenes under mild conditions. While the reaction with Pd nanoparticles on other supporting materials such as modified carbon materials and TiO2, under similar conditions, resulted formation of amines exclusively. Therefore, it was confirmed that the SiO2 was found to be the best supporting material towards the selective reductive coupling of nitroarenes. Also, the catalyst could be recycled up to five cycles with a marginal loss of product yield ( 2% yield). Graphic Abstract: [Figure not available: see fulltext.].