1027-40-3

Usage

Uses

Used in Pharmaceutical Industry:
1,2-bis(4-methoxyphenyl)hydrazine is used as a building block for the synthesis of various pharmaceutical compounds for its versatile reactivity and ability to form biologically active molecules.
Used in Organic Chemistry:
1,2-bis(4-methoxyphenyl)hydrazine is used as a versatile reagent in organic chemistry for its solubility in organic solvents and its role in the preparation of various biologically active compounds.
Used in Anticancer and Antiviral Research:
1,2-bis(4-methoxyphenyl)hydrazine is used as a key intermediate in the synthesis of potential anticancer and antiviral agents due to its potential to form compounds with therapeutic properties.

Upstream product

• 100-17-4 para-methoxynitrobenzene 
• 104-94-9 4-methoxy-aniline 
• 501-58-6 bis(4-methoxyphenyl)diazene 
• 501-58-6 (E)-1,2-bis(4-methoxyphenyl)diazene 
• 1562-94-3 4,4'-azoxy anisole 

Downstream Products

• 501-58-6 bis(4-methoxyphenyl)diazene 

Relevant academic research and scientific papers

Regiospecific acylations of aromatics and selective reductions of azobenzenes over hydrated zirconia

Hydrated zirconia has been found to be an efficient and reusable catalyst for the regiospecific acylations of arenes and selective reductions of azobenzenes to produce benzophenones and hydrazabenzenes respectively.

Atomic Layer Deposition of Iron Sulfide and Its Application as a Catalyst in the Hydrogenation of Azobenzenes

The atomic layer deposition (ALD) of iron sulfide (FeSx) is reported for the first time. The deposition process employs bis(N,N′-di-tert-butylacetamidinato)iron(II) and H2S as the reactants and produces fairly pure, smooth, and well-crystallized FeSx thin films following an ideal self-limiting ALD growth behavior. The FeSx films can be uniformly and conformally deposited into deep narrow trenches with aspect ratios as high as 10:1, which highlights the broad applicability of this ALD process for engineering the surface of complex 3D nanostructures in general. Highly uniform nanoscale FeSx coatings on porous γ-Al2O3 powder were also prepared. This compound shows excellent catalytic activity and selectivity in the hydrogenation of azo compounds under mild reaction conditions, demonstrating the promise of ALD FeSx as a catalyst for organic reactions.

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.

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.

Hydrogen peroxide based oxidation of hydrazines using HBr catalyst

Azo compounds (RN = NR′) are an important class of organic molecules that find wide application in organic synthesis. Herein, we report an efficient, practical and metal-free oxidation of hydrazines (RNH-NHR’) to azo compounds using 5 mol% HBr and hydrogen peroxide as terminal oxidant. This new method has been demonstrated by 40 examples with excellent yields. In addition, we showcased two examples of the one-pot sequential reactions involving our hydrazine oxidation/hydrolysis/Heck reaction or Cu-catalyzed N-arylation with aryl boronic acid. The distinct advantages of this protocol include metal-free catalysis, waste prevention, and easy operation.

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.

Visible-light-promoted oxidative dehydrogenation of hydrazobenzenes and transfer hydrogenation of azobenzenes

Azo compounds are widely used in the pharmaceutical and chemical industries. Here, we report the use of a non-metal photo-redox catalyst, Eosin Y, to synthesize azo compounds from hydrazine derivatives. The use of visible-light with air as the oxidant makes this process sustainable and practical. Moreover, the visible-light-driven, photo-redox-catalyzed transfer hydrogenation of azobenzenes is compatible with a series of hydrogen donors such as phenyl hydrazine and cyclic amines. Compared with traditional (thermal/transition-metal) methods, our process avoids the issue of over-reduction to aniline, which extends the applicability of photo-redox catalysis and confirms it as a useful tool for synthetic organic chemistry.

Convenient reduction of azobenzenes and azoxybenzenes to hydrazobenzenes by sodium dithionite using dioctylviologen as an electron transfer catalyst

Various ezobenzenes and azoxybenzenes were reduced almost quantitatively to the corresponding hydrazobenzenes as sodium dithionite under mild conditions without the formation of aniline derivatives, using dioctyl viologen as an electron-transfer catalyst in acetonitrile-water.

Chemoselective reductive coupling of nitroarenes with magnesium in methanol via single electron transfer

A chemoselective reductive coupling of nitroarenes using magnesium in methanol has been reported at ambient temperature. While the cyano, formyl, methoxycarbonyl, methyl, methoxy, phenyl, amino, and chloro groups are unaffected, iodo and bromo groups undergo dehalogenation but in a slower reaction than the coupling of nitro group. The coupling is believed to be proceeding via SET from Mg to nitroarenes.