21650-51-1

Usage

Uses

Used in Textile Industry:
(E)-4,4'-Dichloroazobenzene is used as a dye in the textile industry for coloring fabrics. Its vibrant yellow hue and ability to adhere to fibers make it a valuable component in the production of textiles.
Used in Plastics Industry:
In the plastics industry, (E)-4,4'-Dichloroazobenzene is utilized as a dye to impart color to various plastic products. Its compatibility with plastic materials and stability during processing contribute to its widespread use in this sector.
Used in Paints and Coatings Industry:
(E)-4,4'-Dichloroazobenzene is also employed as a dye in the manufacturing of paints and coatings. Its colorfastness and resistance to fading make it a preferred choice for enhancing the visual appeal and durability of painted surfaces.
Used as a Precursor in Synthesis:
(E)-4,4'-Dichloroazobenzene serves as a precursor in the synthesis of other azo compounds. Its chemical structure allows for further reactions and modifications, leading to the creation of a diverse range of azo-based products.
Used as a Reagent in Organic Chemistry:
(E)-4,4'-Dichloroazobenzene is also used as a reagent in organic chemical reactions, where it can participate in various processes, such as coupling or substitution reactions, to produce desired products.
Safety and Environmental Considerations:
It is crucial to handle (E)-4,4'-Dichloroazobenzene with care due to its toxicity. It can cause irritation to the eyes, skin, and respiratory system. Additionally, it is considered a potential environmental hazard, and proper disposal measures should be taken to prevent contamination of water and soil.

Upstream product

• 106-47-8 4-chloro-aniline 
• 100-00-5 4-chlorobenzonitrile 
• 614-26-6 4,4'-bis(chloro)azoxybenzene 
• 696-62-8 para-iodoanisole 
• 156741-60-5 17-Nitro-tricyclo[11.3.1.1^5,9]octadeca-1⁽¹⁶⁾,5,7,9⁽¹⁸⁾,13⁽¹⁷⁾,14-hexaene 
• 156741-59-2 6-Nitro-tricyclo[11.3.1.1^5,9]octadeca-1⁽¹⁶⁾,5,7,9⁽¹⁸⁾,13⁽¹⁷⁾,14-hexaene 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 614-26-6 (Z)-1,2-bis(4-chlorophenyl)diazene 1-oxide 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 953-14-0 N,N'-bis(4-chlorophenyl)hydrazine 
• 693-13-0 diisopropyl-carbodiimide 
• 99-92-3 p-aminobenzophenone 
• 94-09-7 p-aminoethylbenzoate 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 953-14-0 N,N'-bis(4-chlorophenyl)hydrazine 
• 106-47-8 4-chloro-aniline 
• 1421276-55-2 2-(4-chlorophenyl)-3-phenyl-5-chloro-2H-indazole 
• 1374253-93-6 (E)-1-(4-chloro-2-iodophenyl)-2-(4-chlorophenyl)diazene 

Relevant academic research and scientific papers

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.

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.

Bifunctional Cs?Au/Co3O4 (Basic and Redox)-Catalyzed Oxidative Synthesis of Aromatic Azo Compounds from Anilines

An eco-friendly alkali-promoted (Cs?Au/Co3O4) catalyst, with redox and basic properties for the oxidative dehydrogenative coupling of anilines to symmetrical and unsymmetrical aromatic azo compounds, was developed. We realized a base additive- and molecular O2 oxidant-free process (using air), with reasonable reusability of the catalyst achieved under milder reaction conditions. Notably, the enhanced catalytic activity was also linked to the increased basic site concentration, low reduction temperatures, and the effect of lattice oxygen on the nanomaterials. The increased basic strength of the cation-promoted catalyst improved the electron density of the active Au species, resulting in higher yields of the desired aromatic azo compounds.

Oxidative dehydrogenation of hydrazines and diarylamines using a polyoxomolybdate-based iron catalyst

We report an efficient method for the oxidative dehydrogenation of hydrazines and diarylamines in aqueous ethanol using Anderson-type polyoxomolybdate-based iron(iii) as a catalyst and hydrogen peroxide as an oxidant. A series of azo compounds and tetraarylhydrazines were obtained in moderate to excellent yields. The reaction conditions and substrate scopes are complementary or superior to those of more established protocols. In addition, the catalyst shows good stability and reusability in water. The preliminary mechanistic studies suggest that a radical process is involved in the reaction.

Tuneable Copper Catalysed Transfer Hydrogenation of Nitrobenzenes to Aniline or Azo Derivatives

A highly versatile and flexible copper nanoparticle (Cu(0) NPs) catalytic system has been developed for the controlled and selective transfer hydrogenation of nitroarene. Interestingly, the final catalytic product is strongly dependent on the nature of the hydrogen donor source. The yield of nitrobenzene reduction to aniline increased from 20% to an almost quantitative yield over a range of alcohols, diols and aminoalcohols. In glycerol at 130 °C aniline was isolated in 93% yield. In ethanolamine, the reaction was conveniently performed at a lower temperature (55 °C) and gave selectively substituted azobenzene (92% yield). Experimental studies provide support for a reaction pathway in which the Cu(0) NPs catalysed transfer hydrogenation of nitrobenzene to aniline proceeds via the condensation route. The high chemoselectivity of both protocols has been proved in experiments on a panel of variously substituted nitroarenes. Enabling technologies, microwaves and ultrasound, used both separately and in combination, have successfully increased the reaction rate and reaction yield. (Figure presented.).

Trichloroisocyanuric Acid Mediated Oxidative Dehydrogenation of Hydrazines: A Practical Chemical Oxidation to Access Azo Compounds

A highly efficient, metal-free, chemical oxidation of hydrazines has been implemented using environmentally friendly TCCA as oxidant. This benign protocol provides straightforward access to a wide range of azo compounds in THF in excellent yield. Altogether, 35 azo compounds were obtained in this way and scale-up preparations were performed. Additionally, a plausible mechanism was also proposed. Step-economical process, mild reaction conditions, operational simplicity, high reaction efficiency, and easy scale-up highlight the practicality of this methodology.

Iron and Nitrogen Co-Doped Mesoporous Carbon-Based Heterogeneous Catalysts for Selective Reduction of Nitroarenes

A facile fabrication of Fe and N co-doped mesoporous carbon (MC), as an efficient heterogeneous catalyst for the highly selective reduction of nitroarenes, is described. The Fe and N co-doped MC nanosheets are easily synthesized via a hydrothermal reaction between citrate acid and magnesium citrate, followed by calcination in the presence of melamine and potassium ferrocyanide. The Fe?N complex provides a unique active site for the selective reduction of 1-chloro-4-nitrobenzene, leading to the production of (E)-1,2-bis(4-chlorophenyl)diazene with a selectivity of >96%, in 40 mins. Control experiments based on non-doped, N-doped, and Fe-doped MC nanosheets demonstrate that selectivity greatly depends on the catalyst active component type, and that non-doped MC significantly contributes to the high efficiencies observed in the selective synthesis of azoxy compound intermediates. A broad range of substrates, including extra-functional groups on the nitroarenes rings, were successfully converted to the corresponding azo compounds at mild conditions with high selectivity. (Figure presented.).

Electrochemical dehydrogenation of hydrazines to azo compounds

A strategy for the electrochemical dehydrogenation of hydrazine compounds is disclosed under ambient conditions. This protocol proceeded smoothly in ethanol by employing electrons as clean oxidants. Its synthetic value is well demonstrated by the highly efficient synthesis of symmetric and unsymmetric azo compounds. It is an environmentally friendly transformation and the present protocol was effective on a large scale.

Cage Encapsulated Gold Nanoparticles as Heterogeneous Photocatalyst for Facile and Selective Reduction of Nitroarenes to Azo Compounds

A discrete nanoscopic organic cage (OC1R) has been synthesized from a phenothiazine based trialdehyde treating with chiral 1,2-cyclohexanediamine building block via dynamic imine bond formation followed by reductive amination. The cage compound has been characterized by several spectroscopic methods, which advocate that OC1R has trigonal prismatic shape formed via [2 + 3] self-assembled imine condensation followed by imine reduction. This newly designed cage has aromatic walls and porous interior decorated with two cyclic thioether and three vicinal diamine moieties suitable for binding gold ions to engineer the controlled nucleation and stabilization of ultrafine gold nanoparticles (AuNPs). The functionalized confined pocket of the cage has been used for the controlled synthesis of AuNPs with narrow size distribution via encapsulation of Au(III) ions. Inductively coupled plasma mass spectrometric (ICP-MS) analysis revealed that the composite Au@OC1R has very high (?68 wt %) gold loading. In distinction, reduction of gold salts in absence of the cage yielded structureless agglomerates. The fine-dispersed cage anchored AuNPs (Au@OC1R) have been finally used as potential heterogeneous photocatalyst for very facile and selective conversion of nitroarenes to respective azo compounds at ambient temperature in just 2 h reaction time. Exceptional chemical stability and reusability without any agglomeration of AuNPs even after several cycles of use are the potential features of this material. The composite Au@OC1R represents the first example of organic cage supported gold nanoparticles as photocatalyst.

A metal-catalyst-free oxidative coupling of anilines to aromatic azo compounds in water using bleach

A simple route toward the synthesis of symmetrical and unsymmetrical aromatic azo compounds through oxidative coupling of anilines using widely available NaOCl is presented. This metal catalyst-free protocol is performed in water and affords the desired products in high yields.