21650-49-7

Basic information

• Product Name: (E)-4-Methoxyazobenzene
• Synonyms: (E)-4-Methoxyazobenzene;Diazene, (4-methoxyphenyl)phenyl-, (E)-
• CAS NO: 21650-49-7
• Molecular Formula: C₁₃H₁₂N₂O
• Molecular Weight: 212.25
• Mol File: 21650-49-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (E)-4-Methoxyazobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-Methoxyazobenzene(21650-49-7)
• EPA Substance Registry System: (E)-4-Methoxyazobenzene(21650-49-7)

Safety Data

• Hazardous Substances Data: 21650-49-7(Hazardous Substances Data)

Upstream product

• 15516-72-0 (Z)-4-methoxyazobenzene 
• 71-43-2 benzene 
• 100-58-3 phenylmagnesium bromide 
• 953-12-8 1-(4-methoxyphenyl)-2-phenylhydrazine 
• 104-94-9 4-methoxy-aniline 
• 62-53-3 aniline 
• 98-95-3 nitrobenzene 
• 108-95-2 phenol 
• 100-17-4 para-methoxynitrobenzene 
• 77-78-1 dimethyl sulfate 
• 1689-82-3 trans-4-hydroxyazobenzene 
• 2396-60-3 4-methoxyazobenzene 
• 74-88-4 methyl iodide 
• 226065-37-8 N-phenyl-hydrazine carboxylic acid tert-butyl ester 

Downstream Products

• 120455-03-0 5-methoxy-2-phenyl-2H-indazole 
• 1578256-92-4 (E)-1-(4-methoxy-3-(trimethylsilyl)phenyl)-2-phenyldiazene 
• 1619236-86-0 (E)-1-(5-methoxy-[1,1’-biphenyl]-2-yl)-2-phenyldiazene 
• 82582-23-8 4-methoxy-N²-phenylbenzene-1,2-diamine 
• 62-53-3 aniline 
• 82582-25-0 1-benzoyl-1-(4-methoxyphenyl)-2-phenylhydrazine 

Relevant articles and documents

Zr(OH)4-Catalyzed Controllable Selective Oxidation of Anilines to Azoxybenzenes, Azobenzenes and Nitrosobenzenes

The selective oxidation of aniline to metastable and valuable azoxybenzene, azobenzene or nitrosobenzene has important practical significance in organic synthesis. However, uncontrollable selectivity and laborious synthesis of the expensive required catalysts severely hinders the uptake of these reactions in industrial settings. Herein, we have pioneered the discovery of Zr(OH)4 as an efficient heterogeneous catalyst capable of the selective oxidation of aniline, using either peroxide or O2 as oxidant, to selectively obtain various azoxybenzenes, symmetric/unsymmetric azobenzenes, as well as nitrosobenzenes, by simply regulating the reaction solvent, without the need for additives. Mechanistic experiments and DFT calculations demonstrate that the activation of H2O2 and O2 is primarily achieved by the bridging hydroxyl and terminal hydroxyl groups of Zr(OH)4, respectively. The present work provides an economical and environmentally friendly strategy for the selective oxidation of aniline in industrial applications.

Oxidative dehydrogenation of hydrazines and diarylamines using a polyoxomolybdate-based iron catalyst

We report an efficient method for the oxidative dehydrogenation of hydrazines and diarylamines in aqueous ethanol using Anderson-type polyoxomolybdate-based iron(iii) as a catalyst and hydrogen peroxide as an oxidant. A series of azo compounds and tetraarylhydrazines were obtained in moderate to excellent yields. The reaction conditions and substrate scopes are complementary or superior to those of more established protocols. In addition, the catalyst shows good stability and reusability in water. The preliminary mechanistic studies suggest that a radical process is involved in the reaction.

Design of phase-transition molecular solar thermal energy storage compounds: compact molecules with high energy densities

A series of compact azobenzene derivatives were investigated as phase-transition molecular solar thermal energy storage compounds that exhibit maximum energy storage densities around 300 J g?1. The relative size and polarity of the functional g

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.

The selective synthesis ofN-arylbenzene-1,2-diamines or 1-arylbenzimidazoles by irradiating 4-methoxy-4′-substituted-azobenzenes in different solvents

The solvent-controllable photoreaction of 4-methoxyazobenzenes to afford 1-aryl-1H-benzimidazoles orN-arylbenzene-1,2-diamines has been studied. The irradiation of 4-methoxyazobenzenes in DMF containing 0.5 M hydrochloric acid providedN2-aryl-4-methoxybenzene-1,2-diamines as the major product, while irradiation in acetal containing 0.16 M hydrochloric acid led to 1-aryl-6-methoxy-2-methyl-1H-benzimidazoles as the major product. A possible reaction mechanism explaining the selectivity was also discussed.

Selective Oxidation of Anilines to Azobenzenes and Azoxybenzenes by a Molecular Mo Oxide Catalyst

Aromatic azo compounds, which play an important role in pharmaceutical and industrial applications, still face great challenges in synthesis. Herein, we report a molybdenum oxide compound, [N(C4H9)4]2[Mo6O19] (1), catalyzed selective oxidation of anilines with hydrogen peroxide as green oxidant. The oxidation of anilines can be realized in a fully selectively fashion to afford various symmetric/asymmetric azobenzene and azoxybenzene compounds, respectively, by changing additive and solvent, avoiding the use of stoichiometric metal oxidants. Preliminary mechanistic investigations suggest the intermediacy of highly active reactive and elusive Mo imido complexes.

Bifunctional Cs?Au/Co3O4 (Basic and Redox)-Catalyzed Oxidative Synthesis of Aromatic Azo Compounds from Anilines

An eco-friendly alkali-promoted (Cs?Au/Co3O4) catalyst, with redox and basic properties for the oxidative dehydrogenative coupling of anilines to symmetrical and unsymmetrical aromatic azo compounds, was developed. We realized a base additive- and molecular O2 oxidant-free process (using air), with reasonable reusability of the catalyst achieved under milder reaction conditions. Notably, the enhanced catalytic activity was also linked to the increased basic site concentration, low reduction temperatures, and the effect of lattice oxygen on the nanomaterials. The increased basic strength of the cation-promoted catalyst improved the electron density of the active Au species, resulting in higher yields of the desired aromatic azo compounds.

Trichloroisocyanuric Acid Mediated Oxidative Dehydrogenation of Hydrazines: A Practical Chemical Oxidation to Access Azo Compounds

A highly efficient, metal-free, chemical oxidation of hydrazines has been implemented using environmentally friendly TCCA as oxidant. This benign protocol provides straightforward access to a wide range of azo compounds in THF in excellent yield. Altogether, 35 azo compounds were obtained in this way and scale-up preparations were performed. Additionally, a plausible mechanism was also proposed. Step-economical process, mild reaction conditions, operational simplicity, high reaction efficiency, and easy scale-up highlight the practicality of this methodology.

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.

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.