949-87-1

Usage

Uses

Used in Plastics Industry:
4-methylazobenzene is used as a dye to impart color to various types of plastics, enhancing their visual appeal and providing a distinctive appearance.
Used in Textile Industry:
In the textile industry, 4-methylazobenzene serves as a dye for coloring fabrics, offering a wide range of color options and contributing to the aesthetic quality of textiles.
Used in Ink Production:
4-methylazobenzene is utilized as a dye in the production of inks, ensuring vibrant and long-lasting color in various printing applications.
Used in Photoresponsive Materials:
Due to its potential photochromic properties, 4-methylazobenzene is studied for use in photoresponsive materials, which could change color or properties upon exposure to light.
Used in Sensor Applications:
The thermochromic properties of 4-methylazobenzene make it a candidate for use in sensors that respond to changes in temperature, offering potential applications in various industries.
It is crucial to handle 4-methylazobenzene with care, as it is classified as a hazardous material, and its use should adhere to proper safety measures.

InChI:InChI=1/C13H12N2/c1-11-7-9-13(10-8-11)15-14-12-5-3-2-4-6-12/h2-10H,1H3

Upstream product

• 106-49-0 p-toluidine 
• 64-19-7 acetic acid 
• 586-96-9 Nitrosobenzene 
• 98-95-3 nitrobenzene 
• 100-65-2 N-Phenylhydroxylamine 
• 15795-42-3 N-sulfinyl-4-methylaniline 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 62-53-3 aniline 
• 23438-23-5 4-hydroxy-4-methyl-cyclohexa-2,5-dienone 
• 100-63-0 phenylhydrazine 
• 722-25-8 4-(p-tolyl)azoaniline 
• 64-17-5 ethanol 
• 621-94-3 1-(4-methylphenyl)-2-phenylhydrazine 
• 99-99-0 1-methyl-4-nitrobenzene 

Downstream Products

• 17170-23-9 1.3.3.4.6.6-Hexaphenyl-2.5-di-p-tolyl-1.2.4.5-tetraaza-3.6-disila-cyclohexan 
• 70113-17-6 4,4'-Diphenylazo-stilben 
• 1562-93-2 4-(2-phenyldiazen-1-yl)benzoic acid 
• 85046-91-9 N,N'-Dibenzyl-N-phenyl-N'-p-tolyl-hydrazine 
• 94547-03-2 4-Methyl-4'-(p-toluolsulfonyl)-azobenzol 
• 17049-62-6 5-methyl-2-phenyl-1,2-dihydro-3H-indazol-3-one 
• 57340-21-3 1-(4-(bromomethyl)phenyl)-2-phenyldiazene 
• 106-49-0 p-toluidine 
• 62-53-3 aniline 
• 621-94-3 1-(4-methylphenyl)-2-phenylhydrazine 
• 582-85-4 5-Methyl-2-phenylazo-phenol 
• 20773-92-6 2-p-Tolylazo-phenol 
• 105972-26-7 5-methyl-N₁-phenylbenzene-1,2-diamine 
• 876479-63-9 acetic acid-(N'-phenyl-N-p-tolyl-hydrazide) 

Relevant academic research and scientific papers

Method for preparing azobenzene and azobenzene compound by electro-catalysis

The invention relates to a method for preparing azobenzene and azoxybenzene compounds through electrocatalysis. Under the conditions of room temperature and inert gas, an aromatic nitro compound is reduced and coupled with an aromatic amino compound to be oxidized through electro-catalysis, and an azoxybenzene compound is obtained. The method has the advantages of mild conditions, high efficiencyand selectivity, and high universality, and can realize the synthesis of asymmetric azobenzene and azoxybenzene compounds.

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.).

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.

Phenyl pyrazole compound containing azo structure and preparation method and application thereof (by machine translation)

The invention discloses a phenyl pyrazole compound containing an azo structure, a preparation method thereof and application, of the phenyl pyrazole compound with the azo structure shown in the formula I in the structure, shown by the invention. The phenyl pyrazole compound containing the azo structure according to the invention has good insecticidal activity, and can be used as a pesticide for pest control. (by machine translation)

TEMPO catalyzed oxidative dehydrogenation of hydrazobenzenes to azobenzenes

A metal-free direct oxidative dehydrogenation approach for the synthesis of azobenzenes from hydrazobenzenes has been developed by using TEMPO as an organocatalyst for the first time. The reaction proceeded in open air under mild reaction conditions. A wide range of hydrazobenzenes readily undergo dehydrogenation to give the corresponding azobenzenes in excellent yields.

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.

Synthetic method for aromatic azo compound based on cyclohexanone aromatization

The invention provides a synthetic method for an aromatic azo compound based on cyclohexanone aromatization, and belongs to the technical field of organic chemistry. The method provided by the invention comprises the step of using iodine and DMSO to promote a cyclohexanone compound and arylhydrazine to condensation and dehydrogenation aromatization, and generating the aromatic azo compound. The synthetic method provided by the invention is capable of conveniently synthesizing the asymmetrical aromatic azo compound, and moderate in condition, wide in substrate applicability, simple and convenient in operation, lower in cost, high in product purity, convenient for separation and purification, and is suitable for large-scale preparation without using acid and transition metal.

Photocatalyzed oxidative dehydrogenation of hydrazobenzenes to azobenzenes

Visible light mediated oxidative dehydrogenation of hydrazobenzenes under an ambient atmosphere using an organic dye as a photocatalyst was reported for the first time. The reaction provides an environmentally benign method for the preparation of azobenzenes in excellent yields with good functional group tolerance.

Preparation method of aromatic azo organic compounds

The invention discloses a preparation method of aromatic azo compounds so as to achieve high-yield preparation of the azo compounds from diaryl hydrazine low in cost and easy to obtain through oxydehydrogenation by an organic oxidant. According to different raw materials, the symmetrical or asymmetric azo compounds can be obtained, a catalyst is not needed, the reaction raw materials and the organic oxidant are low in cost and easy to obtain, conditions are mild and efficient, a reaction can be complete through only a few minutes, the reaction process is smooth and safe, products are easy to separate, and the preparation method accords with the development concept of green chemistry.

Responsive Self-Assembly of Supramolecular Hydrogel Based on Zwitterionic Liquid Asymmetric Gemini Guest

A low-molecular-weight supramolecular hydrogel has been fabricated based on host–guest interactions between β-cyclodextrin (β-CD) and an asymmetric gemini zwitterionic liquid (ZIL) containing an azobenzene and bis(trifluoromethanesulfonyl)imide. Reversible sol–gel phase transitions were triggered by light and temperature. The binding stoichiometry, mainly noncovalent interactions in the hydrogel, photo- and thermoresponsive mechanisms, and mode of inclusion in the complex were studied in detail by NMR spectroscopy, UV/Vis spectroscopy, isothermal titration calorimetry, and control experiments. Interestingly, the β-CD in the complex can be photo-manipulated to shuttle along the guest molecule, accompanied by a change in the circular dichroism signals. Reversible switching of the conductivity accompanies the sol–gel phase transition, which demonstrates the stability of the supramolecular hydrogel and its potential application in multi-stimuli-responsive electric sensor materials.