29418-25-5

Usage

Uses

Used in Organic Synthesis:
(E)-bis(2,4-dimethylphenyl)diazene is used as a reagent in organic synthesis for its high reactivity, allowing for the creation of various complex organic molecules.
Used in Chemical Reactions:
(E)-bis(2,4-dimethylphenyl)diazene serves as a reagent in chemical reactions, facilitating specific transformations and contributing to the advancement of organic chemistry.
Used in Pharmaceutical Industry:
(E)-bis(2,4-dimethylphenyl)diazene holds potential applications in the pharmaceutical industry, where its unique properties may be harnessed for the development of new drugs and therapies.
Used in Material Science:
In the field of material science, (E)-bis(2,4-dimethylphenyl)diazene may be utilized to develop novel materials with specific properties, such as improved reactivity or stability.
Overall, (E)-bis(2,4-dimethylphenyl)diazene is a versatile compound with a wide range of potential applications across various industries, making it a valuable subject of research and development.

Upstream product

• 70853-94-0 N-(2,4-dimethylphenyl)hydroxylamine 
• 95-68-1 2,4-Xylidine 
• 89-87-2 2,4-dimethylnitrobenzene 
• 53559-94-7 2,4-dimethyl-benzenediazonium; chloride 
• 64-17-5 ethanol 
• 7664-93-9 sulfuric acid 
• 25743-21-9 N,N'-bis(2,4-dimethylphenyl)hydrazine 
• 7647-01-0 hydrogenchloride 
• 99766-50-4 bis-(2,4-dimethyl-phenyl)-diazene-N-oxide 

Downstream Products

• 41825-73-4 2-bromo-4,6-dimethylaniline 
• 95-68-1 2,4-Xylidine 
• 25743-21-9 N,N'-bis(2,4-dimethylphenyl)hydrazine 
• 1584667-92-4 (E)-N-(2-((2,4-dimethylphenyl)diazenyl)-3,5-dimethylphenyl)-4-methylbenzenesulfonamide 
• 6328-77-4 N-(2,4-dimethylphenyl)benzamide 

Relevant academic research and scientific papers

Electrosynthesis of Azobenzenes Directly from Nitrobenzenes

The electrochemical reduction strategy of nitrobenzenes is developed. The chemistry occurs under ambient conditions. The protocol uses inert electrodes and the solvent, DMSO, plays a dual role as a reducing agent. Its synthetic value has been demonstrated by the highly efficient synthesis of symmetric, unsymmetric and cyclic azo compounds.

Azo synthesis meets molecular iodine catalysis

A metal-free synthetic protocol for azo compound formation by the direct oxidation of hydrazine HN-NH bonds to azo group functionality catalyzed by molecular iodine is disclosed. The strengths of this reactivity include rapid reaction times, low catalyst loadings, use of ambient dioxygen as a stoichiometric oxidant, and ease of experimental set-up and azo product isolation. Mechanistic studies and density functional theory computations offering insight into this reactivity, as well as the events leading to azo group formation are presented. Collectively, this study expands the potential of main-group element iodine as an inexpensive catalyst, while delivering a useful transformation for forming azo compounds.

Substrate-Controlled Transformation of Azobenzenes to Indazoles and Indoles via Rh(III)-Catalysis

Rh(III)-catalyzed substrate-controlled transformation of azobenzenes to indazoles and 2-acyl (NH) indoles is achieved via C-H functionalization. Generally, good functional groups tolerance, satisfying yields, and excellent regio-selectivity are achieved in this reaction. Mechanistically, the reaction with acrylates undergoes β-hydride elimination, while the reaction with vinyl ketones or acrylamides undergoes nucleophilic addition. Copper acetate was supposed to play different roles in the β-hydride elimination to furnish indazoles and nucleophilic addition of C-Rh bond to deliver 2-acyl (NH) indoles.

Formal [4+2] cycloaddition of 3-ethoxycyclobutanones with azo compounds

Azobenzenes reacted with 3-ethoxycyclobutanoes to give 2,3-dihydro-pyridazin-4(1H)-ones by using EtAlCl2as a Lewis acid. Thus, ring cleavage of 3-ethoxycyclobutanones took place to form a zwitterionic intermediate by activation with EtAlCl2, and intermolecular formal [4+2] cycloaddition of the zwitterionic intermediate proceeded with azobenzenes to give 2,3-dihydro-pyridazin-4(1H)-ones after elimination of ethanol. Regioselectivity for cycloaddition of unsymmetrical azobenzenes, ring contraction and chemoselective reduction of 2,3-dihydro-pyridazin-4(1H)-ones, and [4+2] cycloaddition to 4-phenyl-1,2,4-triazolin-3,5-dione are also described.

Rhenium-Catalyzed [4 + 1] Annulation of Azobenzenes and Aldehydes via Isolable Cyclic Rhenium(I) Complexes

The first Re-catalyzed [4 + 1] annulation of azobenzenes with aldehydes was developed to furnish 2H-indazoles via isolable and characterized cyclic ReI-complexes. For the first time, the acetate-acceleration effect is showcased in Re-catalyzed C-H activation reactions. Remarkably, mechanistic studies revealed an irreversible aldehyde-insertion step, which is in sharp contrast to those of previous Rh- and Co-systems. (Chemical Presented).

Rhenium-catalyzed C-H aminocarbonylation of azobenzenes with isocyanates

The first C-H aminocarbonylation of azobenzenes with isocyanates is achieved by using rhenium-catalysis, which provides an expedient and atom-economical access to varied o-azobenzamides from readily available starting materials. The reaction efficiency can be enhanced by the catalytic use of sodium acetate via accelerated C-H bond activation.

Facile Cu(I)-catalyzed oxidative coupling of anilines to azo compounds and hydrazines with diaziridinone under mild conditions

A mild and highly efficient Cu(I)-catalyzed oxidative coupling of anilines is described. Various primary and secondary anilines can be efficiently coupled under mild conditions to the corresponding azo compounds and hydrazines in high yields. This method provides a direct and practical access to these compounds and is also amenable to gram scale with no special precautions to exclude air or moisture.

Copper-catalyzed aerobic oxidative dehydrogenative coupling of anilines leading to aromatic azo compounds using dioxygen as an oxidant

In the air tonight: A novel approach to symmetric and unsymmetric aromatic azo compounds from simple anilines catalyzed by inexpensive CuBr has been disclosed. Air (or dioxygen) was used as an oxidant under mild reaction conditions, with H2O as the byproduct, to make this transformation environmentally benign and very easy to handle.

Sodium Arenetellurolate Catalyzed Selective Conversion of Nitroaromatics to Aromatic Azoxy or Azo Compounds and Its Application for Facile Preparation of 3,3'- and 4,4'-Bisazobenzenes from (3- and 4-Nitrophenyl)acetylenes

Treatment of aromatic nitro compounds with sodium borohydride in alkaline ethanol in the presence of a catalytic amount of diaryl ditelluride at room temperature affords the corresponding azoxy compounds selectively in fair to excellent yields.Under reflux aromatic azo compounds are obtained as major products.In situ generated sodium arenetellurolate (ArTeNa) is the active species to reduce nitroaromatics into aromatic nitroso compounds, the latter being easily converted into azoxy compounds in alkaline ethanol.Higher temperature enables ArTeNa to reduce the initially produced azoxy compounds into azo compounds.A new vinylic telluride having an azo group in the molecule, 3,3'-bisazobenzene, was prepared in one pot in 66-91percent isolated yield by treating (3-nitrophenyl)acetylene with a stoichiometric amount of ArTeNa in alkaline ethanol at reflux temperature, the structure of which was determined unambiguously by X-ray crystallography.The corresponding 4, 4'-isomer was similarly prepared, but in lower yield.