582-69-4

Basic information

• Product Name: 4,4'-AZOXYDIBENZOIC ACID
• Synonyms: P-AZOXY BENZOIC ACID;TIMTEC-BB SBB008586;4,4'-AZOXYDIBENZOIC ACID;4,4'-ONN-Azoxybisbenzoic acid;Azoxybenzene-4,4'-dicarboxylic acid;(4-carboxyphenyl)-(4-carboxyphenyl)imino-oxidanidyl-azanium;(4-carboxyphenyl)-(4-carboxyphenyl)imino-oxido-ammonium;(4-carboxyphenyl)-(4-carboxyphenyl)imino-oxidoazanium
• CAS NO: 582-69-4
• Molecular Formula: C₁₄H₁₀N₂O₅
• Molecular Weight: 286.24
• Mol File: 582-69-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: 114.5 °C
• Boiling Point: 562.5°C at 760 mmHg
• Flash Point: 294°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 1.72E-13mmHg at 25°C
• Refractive Index: 1.641
• CAS DataBase Reference: 4,4'-AZOXYDIBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-AZOXYDIBENZOIC ACID(582-69-4)
• EPA Substance Registry System: 4,4'-AZOXYDIBENZOIC ACID(582-69-4)

Safety Data

• Hazardous Substances Data: 582-69-4(Hazardous Substances Data)

Usage

General Description

4,4'-AZOXYDIBENZOIC ACID is a chemical compound with the molecular formula C14H10N2O5. It is a yellowish to orange crystalline powder and is soluble in organic solvents. 4,4'-AZOXYDIBENZOIC ACID is primarily used in the production of azo dyes, which are widely used in the textile and paper industries. It is also used as a chemical intermediate in the synthesis of pharmaceuticals and other organic compounds. 4,4'-AZOXYDIBENZOIC ACID is considered to be a hazardous chemical and its handling and disposal should be carried out with caution to prevent harm to human health and the environment.

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 articles and documents

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.

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.].

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.