13556-84-8

Basic information

• Product Name: 2,2'-dichloroazoxybenzene
• Synonyms: 2,2'-dichloroazoxybenzene;2,2′-Dichlorazoxybenzol;Azoxybenzene, 2,2'-dichloro-;Diazene, 1,2-bis(2-chlorophenyl)-, 1-oxide;Diazene, bis(2-chlorophenyl)-, 1-oxide;Einecs 236-941-0;Nsc 83589
• CAS NO: 13556-84-8
• Molecular Formula: C₁₂H₈Cl₂N₂O
• Molecular Weight: 267.11072
• EINECS: 236-941-0
• Mol File: 13556-84-8.mol
• Article Data: 30

Chemical Properties

• Melting Point: 56 °C
• Boiling Point: 409.7°Cat760mmHg
• Flash Point: 201.6°C
• Appearance: /
• Density: 1.33g/cm³
• CAS DataBase Reference: 2,2'-dichloroazoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-dichloroazoxybenzene(13556-84-8)
• EPA Substance Registry System: 2,2'-dichloroazoxybenzene(13556-84-8)

Safety Data

• Hazardous Substances Data: 13556-84-8(Hazardous Substances Data)

Usage

General Description

2,2'-dichloroazoxybenzene is a chemical compound with the molecular formula C12H8Cl2N2O. It is an organic compound that is derived from azobenzene and contains two chlorine atoms. It is used as a reagent in organic chemistry for the oxidation of alcohols to carbonyl compounds. 2,2'-dichloroazoxybenzene is known for its potential as a mutagen and carcinogen, and it is considered toxic and hazardous to human health and the environment. Therefore, it should be handled with care and with proper safety precautions. Its use and disposal should be regulated to minimize the risk of exposure and contamination.

Upstream product

• 50-99-7 D-glucose 
• 88-73-3 2-Chloronitrobenzene 
• 67-56-1 methanol 
• 71-43-2 benzene 
• 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 
• 932-33-2 o-Chloronitrosobenzene 
• 64-17-5 ethanol 
• 19519-75-6 1-bromo-2-nitrosobenzene 
• 124-41-4 sodium methylate 
• 13259-29-5 sodium isobutoxide 

Downstream Products

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

Relevant articles and documents

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 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

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.

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.