13921-71-6

Basic information

• Product Name: 4-Dimethylaminoazoxybenzene
• Synonyms: N,N-Dimethyl-4-(phenyl-ONN-azoxy)benzenamine
• CAS NO: 13921-71-6
• Molecular Formula: C₁₄H₁₅N₃O
• Molecular Weight: 241.29
• Mol File: 13921-71-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Dimethylaminoazoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Dimethylaminoazoxybenzene(13921-71-6)
• EPA Substance Registry System: 4-Dimethylaminoazoxybenzene(13921-71-6)

Safety Data

• Hazardous Substances Data: 13921-71-6(Hazardous Substances Data)

Upstream product

• 13921-67-0 4-(phenyl-ONN-azoxy)-N,N-dimethylaniline amino oxide 
• 60-11-7 methyl yellow 
• 2747-31-1 4-(phenylazo)-N,N-dimethylaniline amino oxide 
• 77-78-1 dimethyl sulfate 
• 60-09-3 4-Aminoazobenzene 
• 3291-89-2 4-(phenyl-NNO-azoxy)-N,N-dimethylaniline 
• 50-00-0 formaldehyd 
• 95633-07-1 4-(phenyl-ONN-azoxy)aniline 
• 100-65-2 N-Phenylhydroxylamine 
• 138-89-6 p-dimethylaminonitrosobenzene 

Downstream Products

• 13921-67-0 4-(phenyl-ONN-azoxy)-N,N-dimethylaniline amino oxide 
• 63020-88-2 4-Dimethylamino-2-hydroxy-azobenzol 
• 4845-14-1 formic acid-(N-methyl-4-phenylazo-anilide) 
• 138-89-6 p-dimethylaminonitrosobenzene 
• 2496-15-3 4-hydroxy-4'-(N,N-dimethylamino)azobenzene 

Relevant articles and documents

Preparation, separation and identification of some para-substituted ONN and NNO trans-azoxybenzenes

A series of para-substituted azoxybenzenes was obtained as model compounds for the investigation on the mechanism of Wallach rearrangement. Oxidation of azobenzenes with hydrogen peroxide in acetic acid solution, provided mixtures of α and β isomers. Some

The Photochemistry of Some Methoxy and Dimethylamino Derivatives of Azoxybenzene

The photochemistry of the six azoxybenzene derivatives carrying a methoxy and/or a dimethylamino group in positions 4/4' has been examined in alcogols and in benzene and found to lead to different processes.The photo-Wallach rearrangement takes place for all except the disubstituted derivatives.This process involves an intermediate, which either gives back the starting azoxy or is converted to the final o-hydroxy derivative through acid catalysis as well as by the previously reported basic catalysis or via cleavage to diazonium ions, which can be trapped before recombination.Oxygen shift to yield the isomeric azoxy derivative (only one precedent known) is a general, one-way process, leading in every case to the azoxy benzene with the N->O group far from the ring carrying the stronger electron-donating substituent.Differently from the photo-Wallach rearrangement, this process shows little solvent dependence.The dimethylamino derivatives undergo also or exclusively different fragmentations, such as intramolecular hydrogen abstraction and cleavage of either the N=N or the C-N bond.The solvent and substituent effect upon electronic spectra, reaction quantum yield, and product distribution are discussed.The photochemistry is attributed to a ?,?* state with strong internal charge transfer.

Photochemical Decomposition of 4-Arylazo- and 4-Arylazoxy-N,N-dialkylaniline N-Oxides

The 4-aryl-N,N-dialkylaniline N-oxides (1a-c) decompose on u.v. irradiation in aprotic solvents, undergoing deoxygenation as well as intramolecular hydrogen abstraction, to give amides and dealkylated products.The latter process is more important for the diethyl derivative (1b) (photoCope elimination).Visible irradiation is ineffective.The 4-arylazoxy-N,N-dialkylaniline N-oxides (2a-d) undergo photochemical deoxygenation from the amino group (major process) as well as from the azo group.The mechanism of these photoprocesses is discussed in general and in relation to the possible involvement of these N-oxide derivatives in photofading of the related azo dyes.

POSITIONAL ISOMERS OF 4-PHENYLAZO-N,N-DIMETHYLANILINE N-OXIDES

A conclusive answer is given to the long-debated question concerning the structure of the N-oxidation products of the title compound. 4-Phenylazoxy-N,N-dimethylanilines were obtained by methylation of 4-phenylazoxyanilines, of established structure.UV spe