4329-74-2

Basic information

• Product Name: Azoxybenzene-4,4'-dicarbaldehyde
• Synonyms: 4,4'-ONN-Azoxybisbenzaldehyde;Azoxybenzene-4,4'-dicarbaldehyde
• CAS NO: 4329-74-2
• Molecular Formula: C₁₄H₁₀N₂O₃
• Molecular Weight: 254.24
• Mol File: 4329-74-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Azoxybenzene-4,4'-dicarbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: Azoxybenzene-4,4'-dicarbaldehyde(4329-74-2)
• EPA Substance Registry System: Azoxybenzene-4,4'-dicarbaldehyde(4329-74-2)

Safety Data

• Hazardous Substances Data: 4329-74-2(Hazardous Substances Data)

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 4329-72-0 1-(4'-nitrobenzyl)pyridinium chloride 
• 104060-84-6 2-(4-nitro-benzylsulfanyl)-benzoic acid 
• 7597-44-6 3-(4-nitro-benzylsulfanyl)-propionic acid 
• 619-73-8 4-nitrobenzyl chloride 
• 110-80-5 2-ethoxy-ethanol 
• 62-53-3 aniline 
• 100-14-1 4-nitrobenzyl chloride 
• 10359-18-9 N-(4-nitrobenzyl)aniline 
• 272786-88-6 1-(N-butylamino)-4'-nitrobenzylphosphonic acid 
• 63207-57-8 1-amino-4'-nitrobenzylphosphonic acid 
• 6421-26-7 bis-[4-(phenylimino-methyl)-phenyl]-diazene-N-oxide 
• 7664-93-9 sulfuric acid 
• 7705-08-0 iron(III) chloride 

Downstream Products

• 122724-63-4 4,4'-azoxy-di-benzaldehyde bis-phenylhydrazone 
• 105122-76-7 4,4'-(4,4'-azoxy-bis-benzylidenamino)-di-benzoic acid diethyl ester 
• 582-69-4 azoxybenzene-4,4'-dicarboxylic acid 
• 88237-19-8 4,4'-azoxy-di-benzaldehyde dihydrazone 
• 37797-35-6 bis-(4-chloromethyl-phenyl)-diazene-N-oxide 
• 130956-40-0 4,4'-azoxy-di-benzaldehyde bis thiosemicarbazone 
• 907177-51-9 4,4''-azoxy-di-chalcone 
• 6421-26-7 bis-[4-(phenylimino-methyl)-phenyl]-diazene-N-oxide 

Relevant articles and documents

Visible light mediated homo- and heterocoupling of benzyl alcohols and benzyl amines on polycrystalline cadmium sulfide

The oxidative coupling of sp3 hybridized carbon atoms by photocatalysis is a valuable synthetic method as stoichiometric oxidation reagents can be avoided and dihydrogen is the only byproduct of the reaction. Cadmium sulfide, a readily available semiconductor, was used as a visible light heterogeneous photocatalyst for the oxidative coupling of benzyl alcohols and benzyl amines by irradiation with blue light. Depending on the structure of the starting material, good to excellent yields of homocoupling products were obtained as mixtures of diastereomers. Cross-coupling between benzyl alcohols and benzyl amines gave product mixtures, but was selective for the coupling of tetrahydroisoquinolines to nitromethane. The results demonstrate that CdS is a suitable visible light photocatalyst for oxidative bond formation under anaerobic conditions.

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.

Mechanism of the Reaction of Sodium Hydroxide and Nitrobenzylsulphones

Aqueous sodium hydroxide reacts with sulphonyl>acetic acid (1) to give 4,4'-diformylazoxybenzene and 4,4'-dicarboxyazoxybenzene as the main products, while in 50percent water-dioxane medium the products are 4,4'-dihydroxymethylazoxybenzene, 4,4'-dicarboxyazoxybenzene besides 4-carboxy, 4'-hydroxymethylazoxybenzene and its isomer. 4-Nitrosobenzaldehyde is an intermediate in this reaction which via a Cannizzaro reaction gives the reaction products.Other 2-, 3- and 4-nitrobenzyl sulphones are studied.