637-47-8

Upstream product

• 99-99-0 1-methyl-4-nitrobenzene 
• 60-29-7 diethyl ether 
• 925-90-6 ethylmagnesium bromide 
• 501-60-0 1,2-di(p-tolyl)diazene 
• 955-98-6 4,4'-Dimethyl-azoxybenzol 
• 71-43-2 benzene 
• 302-01-2 hydrazine 
• 106-49-0 p-toluidine 
• 73183-34-3 bis(pinacol)diborane 
• 106-43-4 para-chlorotoluene 
• 955-98-6 1,2-bis(4-methylphenyl)diazene oxide 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 
• 501-60-0 (E)-4,4'-dimethylazobenzene 

Downstream Products

• 63546-89-4 2,3-di(4-methylphenyl)-2,3-dihydrophthalazin-1,4-dione 
• 22264-20-6 3-(N,N'-Di-p-tolyl-hydrazinocarbonyl)-propionic acid methyl ester 
• 121014-14-0 1,2-Bis(4-methylphenyl)perhydro-3,7-diazepindion 
• 114038-65-2 4,4-dimethyl-1,2-bis(4-methylphenyl)pyrazolidin-3,5-dione 
• 30724-66-4 N,N’-dimethyl-bis(4-methylphenyl)hydrazine 
• 13556-70-2 N-(4-methylphenyl)-5-methyl-1,2-phenylenediamine 
• 501-60-0 1,2-di(p-tolyl)diazene 
• 106-49-0 p-toluidine 
• 501-60-0 (E)-4,4'-dimethylazobenzene 
• 121014-15-1 1,2-Bis<4-(brommethyl)phenyl>perhydro-3,6-pyridazindion 
• 114038-66-3 1,2-Bis<4-(brommethyl)phenyl>-4,4-dimethyl-3,5-pyrazolidindion 
• 121014-16-2 1,2-Bis<4-(brommethyl)phenyl>-perhydro-3,7-diazepindion 
• 125879-63-2 1-acetyl-1,2-bis(4-methylphenyl)hydrazine 
• 55908-53-7 1,2-dihydro-5-methyl-1,2-bis(4-methylphenyl)-3H-pyrazol-3-one 

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.

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.

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.

Tandem selective reduction of nitroarenes catalyzed by palladium nanoclusters

We report a catalytic tandem reduction of nitroarenes by sodium borohydride (NaBH4) in aqueous solution under ambient conditions, which can selectively produce five categories of nitrogen-containing compounds: anilines, N-aryl hydroxylamines, azoxy-, azo- and hydrazo-compounds. The catalyst is in situ-generated ultrasmall palladium nanoclusters (Pd NCs, diameter of 1.3 ± 0.3 nm) from the reduction of Pd(OAc)2 by NaBH4. These highly active Pd NCs are stabilized by surface-coordinated nitroarenes, which inhibit the further growth and aggregation of Pd NCs. By controlling the concentration of Pd(OAc)2 (0.1-0.5 mol% of nitroarene) and NaBH4, the water/ethanol solvent ratio and the tandem reaction sequence, each of the five categories of N-containing compounds can be obtained with excellent yields (up to 98%) in less than 30 min at room temperature. This tunable catalytic tandem reaction works efficiently with a broad range of nitroarene substrates and offers a green and sustainable method for the rapid and large-scale production of valuable N-containing chemicals.

Method for preparing 4, 4'-disubstituted-2, 2'-diaminodiphenyl and hydrochloride thereof through reductive coupling

The invention discloses a method for preparing 4, 4'-disubstituted-2, 2'-diaminodiphenyl and hydrochloride thereof based on 4-substituted nitrobenzene and through reductive coupling. The method comprises the following steps: in the presence of an organic

Selective Photoinduced Reduction of Nitroarenes to N-Arylhydroxylamines

We report the selective photoinduced reduction of nitroarenes to N-arylhydroxylamines. The present methodology facilitates this transformation in the absence of catalyst or additives and uses only light and methylhydrazine. This noncatalytic photoinduced transformation proceeds with a broad scope, excellent functional-group tolerance, and high yields. The potential of this protocol reflects on the selective and straightforward conversion of two general antibiotics, azomycin and chloramphenicol, to the bioactive hydroxylamine species.

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.

Transfer Hydrogenation of Azo Compounds with Ammonia Borane Using a Simple Acyclic Phosphite Precatalyst

Tris(quinolin-8-yl)phosphite, P(Oquin)3, promotes the dehydrogenation of H3N·BH3 (AB) and the transfer hydrogenation of azoarenes using ammonia borane (AB) as H2 source. The metal-free reduction of azoarenes proceeds under mild reaction conditions upon which several diphenylhydrazine derivatives are obtained in high yields. The reactivity of P(Oquin)3 toward AB was evaluated through NMR in situ tests. The rate of the reaction, activation parameters, deuterium kinetic isotope effect (DKIE) and linear-free energy relationship were investigated. Such mechanistic and kinetic studies suggest that P(Oquin)3 is a precatalyst and that AB is likely involved in more than one stage of the reaction pathway. Furthermore, the kinetic data indicate that the reaction proceeds through an ordered transition state, possibly associative.

Bi(I)-Catalyzed Transfer-Hydrogenation with Ammonia-Borane

A catalytic transfer-hydrogenation utilizing a well-defined Bi(I) complex as catalyst and ammonia-borane as transfer agent has been developed. This transformation represents a unique example of low-valent pnictogen catalysis cycling between oxidation states I and III, and proved useful for the hydrogenation of azoarenes and the partial reduction of nitroarenes. Interestingly, the bismuthinidene catalyst performs well in the presence of low-valent transition-metal sensitive functional groups and presents orthogonal reactivity compared to analogous phosphorus-based catalysis. Mechanistic investigations suggest the intermediacy of an elusive bismuthine species, which is proposed to be responsible for the hydrogenation and the formation of hydrogen.

Chemoselective hydrogenation of nitrobenzenes activated with tuned Au/h-BN

The azo- and hydrazo compounds are of great importance in pharmaceuticals, agrochemicals, and chemistry. The controlled reduction of nitroarenes to their coupled products such as aromatic azo and hydrazo compounds has been an interesting area of research synthetically and mechanistically. Herein, we report that the chemoselective catalytic hydrogenation of nitrobenzenes to hydrazobenzenes via azobenzenes can be achieved over gold nanoparticles supported by hexagonal boron nitride nanoplates. It is found that the catalytic process can be successfully conducted not only in N2 but also in air with isopropanol alcohol/KOH. Complete conversion of nitrobenzenes and high selectivity of azobenzenes and hydrazobenzenes have been achieved in one pot under N2 or air atmosphere. Furthermore, as usual unstable intermediates in the reduction process of nitrobenzenes, azobenzenes and hydrazobenzenes can be alternatively harvested as the main product by controlling reaction time or atmosphere. This work shows promise for direct and chemoselective synthesis of azo- and hydrazo compounds under mild conditions in a controllable manner.