61653-33-6

Usage

Uses

Used in Organic Chemistry Research:
(E)-bis(4-ethylphenyl)diazene is used as a research chemical for the development of new synthetic methodologies in the field of organic chemistry. Its unique structure, featuring the diazene double bond, makes it an important target for research and exploration of novel chemical reactions and processes.
Used in Chemical Synthesis:
In the chemical synthesis industry, (E)-bis(4-ethylphenyl)diazene is used as a reactive intermediate or building block for the creation of more complex molecules. Its reactivity and the presence of the diazene double bond allow for the formation of various chemical products through different synthetic pathways.

Upstream product

• 589-16-2 4-aminoethylbenzene 
• 29743-18-8 4-Methoxybenzyliden-4'-aethylanilin 
• 67302-66-3 (4-Ethyl-phenyl)-[1-(4-ethyl-phenyl)-meth-(E)-ylidene]-amine 
• 128654-33-1 1-azido-4-ethylbenzene 
• 90-04-0 2-methoxy-phenylamine 
• 536-90-3 m-Anisidine 
• 100-12-9 4-ethylnitrobenzene 
• 23595-86-0 1,2-bis(4-ethylphenyl)diazene oxide 
• 22955-65-3 1-ethyl-4-nitrosobenzene 
• 67302-70-9 4-nitrobenzylidene-4'-ethylaniline 
• 67302-68-5 RR 294 
• 58761-10-7 (4-Ethyl-phenyl)-[1-p-tolyl-meth-(E)-ylidene]-amine 
• 67302-67-4 N-benzylidene-4-ethylaniline 

Downstream Products

• 23595-86-0 1,2-bis(4-ethylphenyl)diazene oxide 
• 589-16-2 4-aminoethylbenzene 
• 821791-69-9 4-ethyl-2-fluoroaniline 

Relevant academic research and scientific papers

Manganese Catalyzed Hydrogenation of Azo (N=N) Bonds to Amines

We report the first example of homogeneously catalyzed hydrogenation of the N=N bond of azo compounds using a complex of an earth-abundant-metal. The hydrogenation reaction is catalyzed by a manganese pincer complex, proceeds under mild conditions, and yields amines, which makes this methodology a sustainable alternative route for the conversion of azo compounds. A plausible mechanism involving metal-ligand cooperation and hydrazine intermediacy is proposed based on mechanistic studies. (Figure presented.).

Metal- and oxidant-free electrochemically promoted oxidative coupling of amines

The selective oxidation of amines into imines is a priority research topic in organic synthesis and has attracted much attention over the past few decades. However, the oxidation of amines generally suffers from the drawback of transition-metal, even noble-metal catalysts. Thus, the strategy of metal- and oxidant-free selective synthesis of imines is highly desirable yet largely unmet. This paper unravels a metal-free and external oxidant-free electrochemical strategy for the oxidative coupling methodology of amines. This general transformation is compatible with various functional amines and led to functionalized imines in moderate to satisfactory yields.

Nitrate promoted mild and versatile Pd-catalysed C(sp2)-H oxidation with carboxylic acids

A nitrate-promoted Pd-catalysed mild cross-dehydrogenative C(sp2)-H bond oxidation of oximes or azobenzenes with diverse carboxylic acids has been developed. In contrast to the previous catalytic systems, this protocol features mild conditions (close to room temperature for most cases) and a broad substrate scope (up to 64 examples), thus constituting a versatile method to directly prepare diverse O-aryl esters. Moreover, the superiority of the nitrate additive in this mild transformation was further determined by experimental and computational evidence.

Tying the alkoxides together: An iron complex of a new chelating bulky bis(alkoxide) demonstrates selectivity for coupling of non-bulky aryl nitrenes

New chelating bis(alkoxide) ligand H2[OO]Ph and its iron(ii) complex Fe[OO]Ph(THF)2 are described. The coordination of the ligand to the metal center is reminiscent of the coordination of two monodentate alkoxides in previously reported Fe(OR)2(THF)2 species. Fe[OO]Ph(THF)2 catalyzes selective and efficient dimerization of non-bulky aryl nitrenes to yield the corresponding azoarenes.

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.

Palladium-catalyzed cyclizative carbonylation of azobenzenes toward 3H-Indazol-3-ones using formic acid as CO source

A palladium-catalyzed cyclizative carbonylation of azobenzenes has been developed to access 1-acyl 2-aryl 3H-indazol-3-ones in moderate to good yields with good functional compatibility. This procedure proceeded with the sequential ortho-C–H carbonylation and cyclization, where formic acid served as the CO source. The practicability of this transformation was further increased by the employment of facilely available azobenzenes derivatives as one-handled starting materials.

Single-atom dispersed Co-N-C catalyst: Structure identification and performance for hydrogenative coupling of nitroarenes

Co-N-C catalysts are promising candidates for substituting platinum in electrocatalysis and organic transformations. The heterogeneity of the Co species resulting from high-temperature pyrolysis, however, encumbers the structural identification of active sites. Herein, we report a self-supporting Co-N-C catalyst wherein cobalt is dispersed exclusively as single atoms. By using sub-?ngstr?m-resolution HAADF-STEM in combination with XAFS and DFT calculation, the exact structure of the Co-N-C is identified to be CoN4C8-1-2O2, where the Co center atom is coordinated with four pyridinic N atoms in the graphitic layer, while two oxygen molecules are weakly adsorbed on Co atoms in perpendicular to the Co-N4 plane. This single-atom dispersed Co-N-C catalyst presents excellent performance for the chemoselective hydrogenation of nitroarenes to produce azo compounds under mild reaction conditions.

A mild CuBr-NMO oxidative system for the coupling of anilines leading to aromatic azo compounds

An efficient, mild and cost-effective method has been developed utilizing CuBr with N-methylmorpholine N-oxide (NMO/NMMO) for the oxidative coupling of anilines to access symmetrical and unsymmetrical azo compounds in high yield. The reactivity was found to be governed by electronic and steric factors of anilines.

Synthesis of 2,5-diferrocenyl five-membered heterocyclic compounds and their electrochemistry

A series of 2,5-diferrocenyl substituted five-membered heterocyclic compounds, 2,5-diferrocenyl-1-phenylpyrrole (1), 2,5-diferrocenyl-1-(4- fluorophenyl)-pyrrole (2), 2,5-diferrocenyl-1-(4-ethoxyphenyl)-pyrrole (3), 2,5-diferrocenyl-1-(4-ethylphenyl)-pyrrole (4), 2,5-diferrocenylthiophene (5), and 2,5-diferrocenylfuran (6), were synthesized using one-pot cycloaddition of ferrocenyl alkyne and characterized by elemental analysis, FT-IR, MS, and NMR. The molecular structures of 1, 2, 5, and 6 were determined using single-crystal X-ray diffraction. Electronic communication between two ferrocenyl units of 1-6 was investigated using cyclic voltammetry. These compounds have two well-resolved electrochemically reversible one-electron-transfer processes using [NBu4][PF6] as the supporting electrolyte. The electrochemical studies reveal that electronic communication between two ferrocenyl units depend on the heteroatoms.