582-69-4

Usage

Uses

Used in Textile Industry:
4,4'-AZOXYDIBENZOIC ACID is used as a precursor for azo dyes, which are extensively utilized in the textile industry for coloring fabrics. The dyes derived from 4,4'-AZOXYDIBENZOIC ACID offer a wide range of colors and are valued for their colorfastness and stability.
Used in Paper Industry:
In the paper industry, 4,4'-AZOXYDIBENZOIC ACID serves as a crucial component in the production of azo dyes for coloring paper products. The dyes provide vibrant hues and are known for their resistance to fading, making them ideal for various applications.
Used in Pharmaceutical Industry:
4,4'-AZOXYDIBENZOIC ACID is used as a chemical intermediate in the synthesis of pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Organic Compounds Synthesis:
4,4'-AZOXYDIBENZOIC ACID is also employed as an intermediate in the synthesis of other organic compounds, contributing to the creation of a diverse range of chemical products.
Safety Considerations:
Given its classification as a hazardous chemical, 4,4'-AZOXYDIBENZOIC ACID requires careful handling and disposal to prevent adverse effects on human health and the environment. Proper safety measures should be implemented during its use in various industries.

InChI:InChI=1/C14H10N2O5/c17-13(18)9-1-5-11(6-2-9)15-16(21)12-7-3-10(4-8-12)14(19)20/h1-8H,(H,17,18)(H,19,20)/b16-15-

Upstream product

• 619-73-8 4-nitrobenzyl chloride 
• 99-77-4 ethyl 4-nitrobenzoate 
• 619-68-1 4-nitrosobenzoic acid 
• 2387-74-8 1-(4-methoxyphenyl)-2-(4-nitrophenyl)ethane-1,2-dione 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 555-16-8 4-nitrobenzaldehdye 
• 64-19-7 acetic acid 
• 4329-74-2 4,4'-diformylazoxybenzene 
• 1066-30-4 chromium(lll) acetate 
• 71-23-8 propan-1-ol 
• 6819-41-6 sodium n-propoxide 
• 71-43-2 benzene 
• 50-99-7 glucose 
• 62-23-7 4-nitro-benzoic acid 

Downstream Products

• 23663-92-5 dimethyl 4,4'-azoxydibenzoate 
• 47163-83-7 4,4'-azoxydibenzoyl chloride 
• 76580-35-3 4-(4'-methoxy-phenylazo)benzoic acid methyl ester 
• 105299-45-4 4-(4-hydroxphenylazo)benzoic acid 
• 5320-91-2 4,4'-bismethoxycarbonylazobenzene 
• 586-91-4 azobenzene-4,4'-dicarboxylic acid 
• 62327-30-4 4,4'-hydrazo-di-benzoic acid 
• 6421-04-1 4,4'-azoxy-di-benzoic acid diethyl ester 
• 6421-25-6 4,4'-azoxy-di-benzoic acid diallyl ester 

Relevant academic research and scientific papers

In Vitro Reconstitution Reveals a Central Role for the N-Oxygenase PvfB in (Dihydro)pyrazine-N-oxide and Valdiazen Biosynthesis

The Pseudomonas virulence factor (pvf) operon is essential for the biosynthesis of two very different natural product scaffolds: the (dihydro)pyrazine-N-oxides and the diazeniumdiolate, valdiazen. PvfB is a member of the non-heme diiron N-oxygenase enzyme family that commonly convert anilines to their nitroaromatic counterparts. In contrast, we show that PvfB catalyzes N-oxygenation of the α-amine of valine, first to the hydroxylamine and then the nitroso, while linked to the carrier protein of PvfC. PvfB modification of PvfC-tethered valine was observed directly by protein NMR spectroscopy, establishing the intermediacy of the hydroxylamine. This work reveals a central role for PvfB in the biosynthesis of (dihydro)pyrazine-N-oxides and valdiazen.

Nb2O5 supported on mixed oxides catalyzed oxidative and photochemical conversion of anilines to azoxybenzenes

The synthesis of novel supported niobium oxide catalysts and their application for aniline conversion to azoxybenzenes is described. The catalysts were successfully prepared by thermal decomposition of layered double hydroxides (LDHs), containing M2+ (M = Mg2+ and/or Zn2+) and Al3+ as layer cations, followed by niobium oxide incorporation employing the wetness impregnation method. These catalysts were fully characterized by both experimental techniques and theoretical calculations, and then successfully applied to the selective conversion of anilines into azoxybenzene derivatives, with up to 98% conversion and 92% isolated yield in the presence of violet light. Control experiments and DFT calculations revealed that the catalyst has a dual role in this transformation, acting both as a Lewis acid in the oxidative step and as a photocatalyst in the dimerization of the nitrosobenzene intermediate.

Ultrasound-accelerated selective oxidation of primary aromatic amines to azoxy derivatives with trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane catalyzed by Preyssler acid-mediated nano-TiO2

Preyssler-type heteropolyacid supported on TiO2 nanoparticles has been explored as an efficient catalyst in selective oxidation of primary aromatic amines to azoxy derivatives using trans-3,5-dihydroperoxy-3,5-dimethyl- 1,2-dioxolane as oxidant. The reactions proceeded smoothly under mild and green ultrasound-accelerated conditions to afford the products in high yields. The catalyst recovered from the reaction mixture exhibits long-term stability with no significant drop in its catalytic activity. Graphical abstract: [Figure not available: see fulltext.].

Synthesis of E-1-(alkoxy-NNO-azoxy)-2-arylethenes by the reaction of bis(alkoxy-NNO-azoxy)methanes with benzyl halides under conditions of phase-transfer catalysis

Reaction of bis(methoxy- and ethoxy-NNO-azoxy)methane with benzyl halides and alkali under the conditions of a phase-transfer catalysis furnishes in one stage E-1-(alkoxy-NNO-azoxy)-2-arylethene in 21-55% yields. The intermediate products, 1,1-bis(alkoxy-NNO-azoxy)-2-arylethanes under the action of alkali eliminate one of the two alkoxy-NNO-azoxy groups with the formation of a double bond. The optimum solvent is DMSO, and as benzyl halides, benzyl chlorides. In the case of 4-bromobenzyl bromide a formation was found of a side bisbenzylation product, 1,3-bis(4-bromophenyl)-2,2-bis(methoxy-NNO-azoxy)propane.

Reduction of nitroarenes to azoxybenzenes by potassium borohydride in water

The synthesis of the azoxybenzenes by the reduction of nitroarenes with reducing agent potassium borohydride in water was reported for the first time. PEG-400 was used as a phase transfer catalyst and could effectively catalyze the reduction. The electronic effects of substituent groups play an important role in determining the reduction efficiencies. Electron-withdrawing substituents promote the formation of the azoxybenzene products, while electron-releasing groups retard the reductions to various degrees depending on the extent of their electron-donating ability.

An easy access to aromatic azo compounds under ultrasound/microwave irradiation

Chemoselective reduction of nitroarenes to azo and azoxy compounds was easily achieved using zinc powder and ammonium chloride in DMF or DMF-water (95:5) under high intensity ultrasound (US) or microwave (MW) irradiation, separately or combined. When carried out under conventional heating the reaction required much higher temperatures and gave lower yields. The addition of a small amount of water caused a dramatic increase in the reactivity, permitting the reduction of hindered nitroarenes at the expense of selectivity. A novel reactor for combined US/MW irradiation was employed which demonstrated additional beneficial effects. Georg Thieme Verlag Stuttgart.

Selective reduction of aromatic nitro compounds to azoxy compounds with zinc/aluminium chloride reagent

Aromatic azoxy compounds have been prepared in good yields by the selective reduction of aromatic nitro compounds with Zn/AlCl3 reagent.

Synthesis, Spectral Studies and C-S Bond Fission of Some Alkyl- Diacetates

Some methyl and ethyl diacetates have been synthesized and their structures were identified. A correlation was found between δ-values of benzylidene protons and ?-Hammett values. The internal chemical shift of the methylene proton was found to be structural and applied field dependent. The carbon-sulfur bond fission by the action of sodium hydroxide solution in 50 percent aqueous-dioxane medium, in addition to the alkaline ester hydrolysis was studied. 2- or 4-Nitro compounds gave dicarboxyazoxybenzenes. This led to the suggestion that the reaction might proceed through two intermediates namely diacetic acid and nitrosobenzoic acid. However, the C-S bond fission of other compounds gave aldehydes, supporting that, no α-proton abstraction took place for these compounds.

Nitrobenzyl (α-amino)phosphonates. Part 2[1]. Cleavage of 4-nitrobenzyl(α-amino)phosphonic acids in aqueous sodium hydroxide solution

4-Nitrobenzyl(α-amino)phosphonic acids treated with an excess of aqueous sodium hydroxide undergo a C-P bond cleavage and subsequent transformation into a mixture of azoxybenzene and azobenzene derivatives. The observed cleavage is an example of the intramolecular redox reaction. The phosphonate moiety is oxidized to phosphate, and the remaining part of the molecule is reduced to azoxybenzene derivative 2. After acidification of the reaction mixture two main products were isolated; 4,4′-diformylazoxybenzene (3) and 4-formyl-4′-hydroxyazobenzene (4). The product 4 was probably formed as a result of the Wallach type rearrangement of 3.

Oxidation of Primary Aromatic Amines, Catalyzed by Tungsten Compounds

Treatment of o-nitroanilines and o-aminobenzoic acids with 30 percent hydrogen peroxide in the presence of Na2WO4 and H3PO4 results in selective formation of corresponding nitroso derivatives.In other cases, the products are azoxy compounds.Oxidation of anilines containing alkyl or alkoxy groups in the ortho and para positions with hydrogen peroxide in the presence of Na2WO4 and tetrabutylammonium bromide quantitatively yields corresponding nitrosobenzenes.The H2O2-Na2WO4-H3PO4 system in the presence of tetrabutylammonium bromide is proposed for preparation of nitroso derivatives from anilines containing electron-acceptor meta and para substituents.