13556-84-8

Usage

Uses

Used in Organic Chemistry:
2,2'-dichloroazoxybenzene is used as a reagent for the oxidation of alcohols to carbonyl compounds, a critical transformation in organic synthesis for the production of various organic compounds and pharmaceuticals.
Used in Research and Development:
Due to its mutagen and carcinogen properties, 2,2'-dichloroazoxybenzene may be utilized in research settings to study the mechanisms of mutagenicity and carcinogenicity, potentially leading to the development of countermeasures or preventative strategies against these harmful effects.
Used in Regulatory and Safety Assessments:
Given its toxic and hazardous nature, 2,2'-dichloroazoxybenzene is also used in the context of regulatory and safety assessments to establish guidelines and protocols for its safe handling, use, and disposal, ensuring minimal risk to human health and the environment.

Upstream product

• 13259-29-5 sodium isobutoxide 
• 88-73-3 2-Chloronitrobenzene 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 71-43-2 benzene 
• 932-33-2 o-Chloronitrosobenzene 
• 13154-14-8 1-propenylmagnesium bromide 
• 50-99-7 D-glucose 
• 78-83-1 2-methyl-propan-1-ol 
• 98-95-3 nitrobenzene 
• 123-91-1 1,4-dioxane 
• 10468-16-3 2-chloro-N-hydroxybenzenamine 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 64-17-5 ethanol 

Downstream Products

• 95-51-2 o-chloroaniline 
• 7334-33-0 2,2'-dichloroazobenzene 
• 73626-14-9 3-chloro-4-(2-chloro-phenylazo)-phenol 
• 782-74-1 1,2-bis(2-chlorophenyl)hydrazine 

Relevant academic research and scientific papers

The effect of the catalyst on the synthesis of 2,2′- dichlorohydrazobenzene during the electrochemical reduction of o-chloronitrobenzene

In this paper, 2,2′-dichlorohydrazobenzene was synthesized by the electrochemical reduction of o-chloronitrobenzene using the ion-exchange membrane method. The effects of different catalysts (litharge, lead tetroxide, and lead nitrate) on the synthesis were investigated. The influence of different catalyst loading approaches on the electrochemical reduction were also examined. The structure and surface morphology of the catalysts were characterized by X-ray diffraction and scanning electron microscopy. Catalyst activity was examined by dynamic potential analyses and cyclic voltammetry. Litharge was found to induce the greatest improvement in the electrolysis reaction rate and also decreases the reaction time. Coating the catalyst on the cathode helps enhance the product yield. The possible reaction mechanism was studied, and the catalyst was found to play a key role in transforming raw substances into intermediates. However, there is little effect on intermediate product transformation into the desired product.

The reaction of 2-chloro-4-nitrophenol and the isomeric chloronitrobenzenes with LDA under aryne-forming conditions

The unprecedented base-initiated generation of a nitrobenzyne and subsequent addition of preformed arylacetonitrile anion nucleophiles is reported. In all cases, 2-amino-5-nitro-3-benzo[b]furans are obtained as major product with small amounts of 3-arylmethyl-2-cyano-4-nitrophenols. A mechanism involving ring closure of phenoxide and nitrile groups of the initial aryne-nitrile anion adduct is proposed to account for the formation of the benzofurans. The three isomeric chloronitrobenzynes, however, do not give aryne products when treated with LDA, but rather are reduced to the corresponding bis-dichloroazoxybenzenes.

The effect of water on the hydrogenation of o-chloronitrobenzene in ethanol, n-heptane and compressed carbon dioxide

Water as a clean solvent and promoter in the organic synthesis have attracted more attention, herein the effect of water was studied for the hydrogenation of o-chloronitrobenzene (o-CNB) over Pt/C and Pd/C catalysts in ethanol, n-heptane and compressed CO2. Very interesting, the reaction rate decreased in ethanol, but increased in n-heptane and compressed CO 2 with the addition of water. The role of water in the reaction was mainly discussed from the experimental data and phase behavior analysis, one is to activate the functional group of NO2 through the interactions via a hydrogen bonding, and the other is to affect the solubility of hydrogen in ethanol and n-heptane. The positive effect of the interaction between water and reactants may be counteracted by the negative effect of hydrogen solubility in ethanol. However, the concentration of o-CNB and hydrogen changed slightly in n-heptane with the addition of water, so the interaction of water with reactants may play a main role in improving the TOF. The combination of H2O and CO2 is more efficient than the pure H2O, CO 2 and H2O-n-heptane systems. The phase behavior may play important role also for the improved activity except for the interactions of H2O and CO2 with the reactants. o-CNB phase was expanded in the compressed CO2 and so the concentration of H2 in o-CNB phase increased due to the miscible of CO2 and H2, resulting in the enhancement of reaction rate and the maximum conversion at pressure of 9 MPa CO2, at which the volume was expanded to the largest one. The similar results were also obtained in the compressed CO 2 system without H2O. In addition, the stability of Pt/C and Pd/C was studied in H2O-n-heptane and H2O-CO 2. As a result, the H2O-CO2 media and Pt/C catalyst is one of the most effective systems for the hydrogenation of o-CNB.

Selective hydrogenation of chloronitrobenzene to chloroaniline in supercritical carbon dioxide over Ni/TiO2: Significance of molecular interactions

The hydrogenation of chloronitrobenzene to chloroaniline was investigated over Ni/TiO2 at 35 °C in supercritical CO2 (scCO2), ethanol, and n-hexane. The reaction rate followed the order of scCO2 > n-hexane > eth

METHOD OF REDUCING AROMATIC NITRO COMPOUNDS

A method for reducing a substrate selected from 2-methyl-5-nitropyridine and methyl 4-(2-fluoro-3-nitrobenzyl)piperazine-1-carboxylate is provided catalysed by a nitroreductase and a disproportionation agent.

Chemoselective electrochemical reduction of nitroarenes with gaseous ammonia

Valuable aromatic nitrogen compounds can be synthesized by reduction of nitroarenes. Herein, we report electrochemical reduction of nitroarenes by a protocol that uses inert graphite felt as electrodes and ammonia as a reductant. Depending on the cell voltage and the solvent, the protocol can be used to obtain aromatic azoxy, azo, and hydrazo compounds, as well as aniline derivatives with high chemoselectivities. The protocol can be readily scaled up to >10 g with no decrease in yield, demonstrating its potential synthetic utility. A stepwise cathodic reduction pathway was proposed to account for the generations of products in turn.

Preparation of niobium or tantalum complex and application of niobium or tantalum complex in catalyzing aromatic amine to generate oxidized azobenzene compound

The invention provides a preparation method of niobium or tantalum complex and an application of the niobium or tantalum complex in catalyzing aromatic amine to generate an oxidized azobenzene compound. The preparation method of the complex comprises A hydration oxide preparation, @timetime@ niobium oxide or tantalum oxide and strong base in 300 - 800 °C melting calcination 2 - 8h, adding water to dissolve and filter, and then adjusting pH through 4-6, suction filtration and drying. The B complex is prepared by mixing a hydrated oxide with a molar ratio 10-25: 1 with hydrogen peroxide, adding an organic acid and a cationic precursor after clarifying the solution, and evaporating and drying to obtain a niobium complex or a tantalum complex. The molar ratio @timetime@: 1-3. In the method for synthesizing the oxidized azobenzene compound by using niobium or tantalum complex as a catalyst, ethanol is used as a solvent, hydrogen peroxide is used as an oxidant, niobium complex or tantalum complex is used as a catalyst, and the addition amount is ppm.

The polyhedral nature of selenium-catalysed reactions: Se(iv) species instead of Se(vi) species make the difference in the on water selenium-mediated oxidation of arylamines

Selenium-catalysed oxidations are highly sought after in organic synthesis and biology. Herein, we report our studies on the on water selenium mediated oxidation of anilines. In the presence of diphenyl diselenide or benzeneseleninic acid, anilines react with hydrogen peroxide, providing direct and selective access to nitroarenes. On the other hand, the use of selenium dioxide or sodium selenite leads to azoxyarenes. Careful mechanistic analysis and 77Se NMR studies revealed that only Se(iv) species, such as benzeneperoxyseleninic acid, are the active oxidants involved in the catalytic cycle operating in water and leading to nitroarenes. While other selenium-catalysed oxidations occurring in organic solvents have been recently demonstrated to proceed through Se(vi) key intermediates, the on water oxidation of anilines to nitroarenes does not. These findings shed new light on the multifaceted nature of organoselenium-catalysed transformations and open new directions to exploit selenium-based catalysis.

Preparation of azoxy benzene (by machine translation)

[A] good workability and safety, cost, and, efficient production of the azoxy benzene azoxy benzene can be produced. [Solution] nitrobenzene ones, having the photocatalytic function with a dye, a reducing agent such as a fluorine resin or a transparent resin material is a mixed solution of 1 mm in diameter are inserted into the tube 4 does not inhibit the reaction, 4 LED lamp 5 emits visible from the outside of the tube moves within the tube 4 is provided with visible light within the tube 4 by a photocatalyst reaction mixed solution so as to obtain azoxy benzene compounds. Figure 2 [drawing] (by machine translation)

A Co2B Mediated NaBH4 Reduction Protocol Applicable to a Selection of Functional Groups in Organic Synthesis

A high-yielding and high-rate reduction method that operates with alkenes, alkynes, azides, nitriles, and nitroarenes was developed and optimized. The method makes use of sodium borohydride reduction of CoSO4 under release of hydrogen along with the formation of Co2B as a nanoparticle material. The produced Co2B activates the various functional groups for hydride reduction. The protocol was proven to operate with an assortment of functional groups to provide good to excellent yields. Furthermore, the reduction method was successfully adapted, implemented, and developed for a continuous flow approach using the multi-jet oscillating disk (MJOD) flow reactor platform at atmospheric pressure.