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Usage

Uses

Used in Pharmaceutical Research:
1-(4-chlorophenyl)-2-phenylhydrazine is used as a reagent for [application reason] in pharmaceutical research. It serves as an important intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapies.
Used in Organic Synthesis:
1-(4-chlorophenyl)-2-phenylhydrazine is used as an intermediate for [application reason] in organic synthesis. Its unique chemical structure allows for the creation of a wide range of organic compounds, making it a valuable component in the synthesis of various agrochemicals and other products.
Used in Cancer Treatment:
1-(4-chlorophenyl)-2-phenylhydrazine is used as a potential therapeutic agent for [application reason] in the treatment of cancer. Its cytotoxic properties are being studied for their potential to target and eliminate cancer cells, offering a new avenue for cancer treatment and management.
Used in Anticonvulsant Development:
1-(4-chlorophenyl)-2-phenylhydrazine is used as a compound with potential anticonvulsant properties for [application reason] in the development of treatments for seizure disorders. Its ability to modulate certain neurological pathways may provide a new approach to managing epilepsy and other related conditions.

Upstream product

• 4340-77-6 4-chloroazobenzene 
• 6141-95-3 trans-(4-chloro-phenyl)-phenyl-diazene 
• 3457-98-5 4-phenylazoaniline hydrochloride 
• 106-47-8 4-chloro-aniline 
• 98-95-3 nitrobenzene 
• 100-00-5 4-chlorobenzonitrile 
• 586-96-9 Nitrosobenzene 

Downstream Products

• 13065-93-5 4-amino-4'-chlorodiphenylamine 
• 68406-47-3 4-chloro-N₂-phenylbenzene-1,2-diamine 
• 106-47-8 4-chloro-aniline 
• 92-87-5 p,p'-diaminobiphenyl 
• 4340-77-6 4-chloroazobenzene 
• 62-53-3 aniline 
• 308817-89-2 2-(4'-aminophenyl)-4-chloroaniline 
• 6141-95-3 trans-(4-chloro-phenyl)-phenyl-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.

Chemoselective Hydrogenation of Nitroarenes Using an Air-Stable Base-Metal Catalyst

The reduction of nitroarenes to anilines as well as azobenzenes to hydrazobenzenes using a single base-metal catalyst is reported. The hydrogenation reactions are performed with an air-and moisture-stable manganese catalyst and proceed under relatively mild reaction conditions. The transformation tolerates a broad range of functional groups, affording aniline derivatives and hydrazobenzenes in high yields. Mechanistic studies suggest that the reaction proceeds via a bifunctional activation involving metal-ligand cooperative catalysis.

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.

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.

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.

Dehydrogenation of the NH?NH Bond Triggered by Potassium tert-Butoxide in Liquid Ammonia

A novel strategy for the dehydrogenation of the NH?NH bond is disclosed using potassium tert-butoxide (tBuOK) in liquid ammonia (NH3) under air at room temperature. Its synthetic value is well demonstrated by the highly efficient synthesis of aromatic azo compounds (up to 100 % yield, 3 min), heterocyclic azo compounds, and dehydrazination of phenylhydrazine. The broad application of this strategy and its benefit to chemical biology is proved by a novel, convenient, one-pot synthesis of aliphatic diazirines, which are important photoreactive agents for photoaffinity labeling.

Reactions of Azoarenes with Tributyltin Hydride

Tributyltin hydride when reacted with a series of substituted azoarenes afforded hydrazo compounds with high chemoselectivity and good to high yields.With ortho-substituted azoarenes, mixtures of hydrazo derivatives and N-heterocycles or cyclic products only were obtained.The kinetic law of the process was determined in the presence and in the absence of AIBN; with the radical initiator the reaction proceeds via a radical chain mechanism, whereas without AIBN the presence of stannyl free radicals could be discarded.The mechanism of the noninitiated reaction is discussed.EPR characterization of spin adducts obtained by reacting group IVB organometallic radicals with azo compounds is reported.

Heterogeneous Photocatalytic Reactions of Azobenzenes on Titanium Dioxide Powder in Methanolic Solution

Irradiation of a TiO2 powder suspension in a methanolic solution of an azobenzene results in the formation of 1,2,4-triphenyl-1,2,4-triazolidines and a 2-phenylindazole in moderate yields.