782-74-1

Usage

Uses

Used in Pharmaceutical Synthesis:
1,2-bis(2-chlorophenyl)hydrazine is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic benefits.
Used in Agrochemical Production:
In the agrochemical industry, 1,2-bis(2-chlorophenyl)hydrazine is utilized as a precursor in the production of agrochemicals, which are essential for enhancing crop protection and yield.
Used in Dye and Pigment Manufacturing:
1,2-bis(2-chlorophenyl)hydrazine is employed as a building block in the manufacturing of dyes and pigments, contributing to the creation of a wide range of colorants used in various industries, such as textiles, plastics, and printing inks.
Used in Research and Development:
1,2-bis(2-chlorophenyl)hydrazine is used as a research chemical for studying its potential biological activity and exploring its applications in the treatment of certain medical conditions, thereby contributing to advancements in medical science.

InChI:InChI=1/C12H10Cl2N2/c13-9-5-1-3-7-11(9)15-16-12-8-4-2-6-10(12)14/h1-8,15-16H

Upstream product

• 88-73-3 2-Chloronitrobenzene 
• 7334-33-0 2,2'-dichloroazobenzene 
• 13556-84-8 2,2'-azoxychlorobenzene 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 71-43-2 benzene 
• 49795-06-4 (E)-bis(2-chlorophenyl)diazene 
• 91-94-1 3,3'-dichlorobenzidine 
• 13556-84-8 2,2'-dichloroazoxybenzene 
• 95-51-2 o-chloroaniline 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 

Downstream Products

• 137182-65-1 4-acetyl-1,2-bis(2-chlorophenyl)-1,2-dihydro-5-methyl-3H-pyrazol-3-one 
• 55908-54-8 1,2-bis(2-chlorophenyl)-1,2-dihydro-5-methyl-3H-pyrazol-3-one 
• 7334-33-0 2,2'-dichloroazobenzene 
• 91-94-1 3,3'-dichlorobenzidine 
• 95-51-2 o-chloroaniline 
• 122-66-7 diphenyl hydrazine 
• 91-94-1 3,3'-dichlorobenzidine HCl 
• 49795-06-4 (E)-bis(2-chlorophenyl)diazene 

Relevant academic research and scientific papers

Visible-Light-Promoted Diboron-Mediated Transfer Hydrogenation of Azobenzenes to Hydrazobenzenes

A visible-light-promoted transfer hydrogenation of azobenzenes has been developed. In the presence of B2pin2 and upon visible-light irradiation, the reactions proceeded smoothly in methanol at ambient temperature. The azobenzenes with diverse functional groups have been reduced to the corresponding hydrazobenzenes with a yield of up to 96%. Preliminary mechanistic studies indicated that the hydrogen atom comes from the solvent and the transformation is achieved through a radical pathway.

Visible-light-promoted decarboxylative addition cyclization of: N -aryl glycines and azobenzenes to access 1,2,4-triazolidines

Methods for the synthesis of 1,2,4-triazolidines are scarce. Herein, we report a visible-light-promoted decarboxylative addition cyclization of N-aryl glycines and azobenzenes to access such important compounds. Using commercially available methylene blue (MB) as an organic photocatalyst, the reaction proceeded smoothly in the absence of transition-metal catalysts at ambient temperature, affording the corresponding products, 1,2,4-triaryl 1,2,4-triazolidines, in good to excellent yields. This work demonstrates a new synthetic application of readily available azobenenes and provides a novel strategy for constructing 1,2,4-triazolidines.

Convenient semihydrogenation of azoarenes to hydrazoarenes using H2

The high atom-economical and eco-benign nature of hydrogenation reactions make them much more superior to conventional reduction and transfer hydrogenation. Herein, a convenient and highly selective hydrogenation reaction of azoarenes using molecular hydrogen to access diverse hydrazoarenes is reported. The present catalytic method is general and operationally simple, and it operates under exceedingly mild conditions (room temperature and 1 atm of hydrogen pressure). The reusability of catalysts used in this method is also successfully demonstrated.

Production process of 3, 3'-dichlorobenzidine hydrochloride

The invention relates to a production process of 3, 3'-dichlorobenzidine hydrochloride, which belongs to the field of organic chemical industry, and is characterized in that o-nitrochlorobenzene is used as a main raw material to carry out catalytic hydrogenation reduction reaction, the obtained reduction product is rectified, and then the rectified target product 2, 2-dichlorohydroazobenzene is subjected to transposition and separation to obtain the 3, 3'-dichlorobenzidine hydrochloride. According to the method, zero emission of waste acid in production of 3, 3'-dichlorobenzidine is realized, waste acid pollution is completely eradicated, the key problem restricting production of 3, 3-dichlorobenzidine is solved, the byproduct 2-chloroaniline is realized, the economic benefit is improved, in addition, the production procedures are greatly reduced, the production efficiency is improved, and the energy consumption is reduced.

Synthesis of novel 1,2-diarylpyrazolidin-3-one–based compounds and their evaluation as broad spectrum antibacterial agents

There is a continuous need to develop new antibacterial agents with non-traditional mechanisms to combat the nonstop emerging resistance to most of the antibiotics used in clinical settings. We identified novel pyrazolidinone derivatives as antibacterial hits in an in-house library screening and synthesized several derivatives in order to improve the potency and increase the polarity of the discovered hit compounds. The oxime derivative 24 exhibited promising antibacterial activity against E. coli TolC, B. subtilis and S. aureus with MIC values of 4, 10 and 20 μg/mL, respectively. The new lead compound 24 was found to exhibit a weak dual inhibitory activity against both the E. coli MurA and MurB enzymes with IC50 values of 88.1 and 79.5 μM, respectively, which could partially explain its antibacterial effect. A comparison with the previously reported, structurally related pyrazolidinediones suggested that the oxime functionality at position 4 enhanced the activity against MurA and recovered the activity against the MurB enzyme. Compound 24 can serve as a lead for further development of novel and safe antibiotics with potential broad spectrum activity.

A switchable-selectivity multiple-interface Ni-WC hybrid catalyst for efficient nitroarene reduction

Selective reduction of nitroarenes is extremely valuable in industrial chemical production. The main reduced products are usually aniline derivatives obtained using single-component noble- or transition-metal catalysts; however, other important products such as hydrazobenzene derivatives always involve in harsh conditions and multiple reaction steps. Here, we realize an unexpected switchable reduction of nitroarenes into aniline or hydrazobenzene derivatives with high yield and selectivity just by controlling the molar ratio of nitroarenes to N2H4·H2O with a nickel–tungsten carbide composite nanocatalyst loaded on carbon (Ni-WC/C). A series of control experiments and density functional theory (DFT) calculations indicate that the multiple interfaces between Ni and WC can induce a synergistic effect, significantly modulating the electronic structure of the Ni-WC/C catalyst, and endowing the catalyst with switchable selectivity and high activity for the reduction of nitroarenes by hydrogenation. This synergistic multi-interfacial catalyst may offer a new way to design and explore highly efficient and selective catalysts for the controllable reduction of nitroarenes and similar hydrogenation reactions.

A concerted transfer hydrogenolysis: 1,3,2-diazaphospholene-catalyzed hydrogenation of Ni-34;N bond with ammonia-borane

1,3,2-diazaphospholenes catalyze metal-free transfer hydrogenation of a Ni-34;N double bond using ammonia-borane under mild reaction conditions, thus allowing access to various hydrazine derivatives. Kinetic and computational studies revealed that the rate-determining step involves simultaneous breakage of the B-H and N-H bonds of ammonia-borane. The reaction is therefore viewed as a concerted type of hydrogenolysis. On the double: Diazaphospholenes catalyze the transfer hydrogenation of a Ni-34;N bond under mild reaction conditions, allowing access to various hydrazine derivatives. The catalytic cycle involves two key steps, and the catalyst maintains the PIII oxidation state throughout the catalytic cycle. The reaction mechanism involves a hydrogenolysis of the exocyclic P-N bond of the intermediate by ammonia-borane, and it proceeds in a concerted double-hydrogen-transfer fashion.

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.

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.

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