17478-75-0

Basic information

• Product Name: Diazene, (4-methoxyphenyl)phenyl-, 2-oxide
• CAS NO: 17478-75-0
• Molecular Formula: C13H12N2O2
• Molecular Weight: 228.25
• Mol File: 17478-75-0.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Diazene, (4-methoxyphenyl)phenyl-, 2-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Diazene, (4-methoxyphenyl)phenyl-, 2-oxide(17478-75-0)
• EPA Substance Registry System: Diazene, (4-methoxyphenyl)phenyl-, 2-oxide(17478-75-0)

Safety Data

• Hazardous Substances Data: 17478-75-0(Hazardous Substances Data)

Upstream product

• 2396-60-3 4-methoxyazobenzene 
• 100-17-4 para-methoxynitrobenzene 
• 98-95-3 nitrobenzene 
• 104-94-9 4-methoxy-aniline 
• 586-96-9 Nitrosobenzene 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 16046-28-9 N'-p-Toluolsulfonyloxy-N-phenyl-diimid-N-oxid 
• 16046-28-9 N-Phenyl-N'-tosyloxydiimid-N-oxid 
• 21650-49-7 (E)-1-(4-methoxyphenyl)-2-phenyldiazene 
• 17478-80-7 (4-methoxyphenyl)phenyldiazene 1-oxide 

Downstream Products

• 1334951-11-9 2-(4-methoxyphenyl)-3-phenyl-2H-indazole 
• 125415-14-7 methyl 2-(4-methoxyphenyl)-2H-indazole-3-carboxylate 
• 56661-22-4 2-hydroxy-4-methoxyazobenzene 
• 842-07-9 Sudan I 
• 2396-60-3 4-methoxyazobenzene 
• 2496-25-5 4-Hydroxy-4'-methoxyazobenzene 

Relevant articles and documents

Chemoselective electrochemical reduction of nitroarenes with gaseous ammonia

Valuable aromatic nitrogen compounds can be synthesized by reduction of nitroarenes. Herein, we report electrochemical reduction of nitroarenes by a protocol that uses inert graphite felt as electrodes and ammonia as a reductant. Depending on the cell voltage and the solvent, the protocol can be used to obtain aromatic azoxy, azo, and hydrazo compounds, as well as aniline derivatives with high chemoselectivities. The protocol can be readily scaled up to >10 g with no decrease in yield, demonstrating its potential synthetic utility. A stepwise cathodic reduction pathway was proposed to account for the generations of products in turn.

Synthesis of Unsymmetrical Aromatic Azoxy Compounds by Silver-Mediated Oxidative Coupling of Aromatic Amines with Nitrosoarenes

A silver(I) oxide-mediated synthesis of unsymmetrical aromatic azoxy compounds has been successfully achieved, wherein oxidative coupling reactions between aromatic amines and nitrosoarenes take place in ethanol under air. This reaction has very high economic value because silver(I) oxide is the only oxidant required and no other additive is needed. The resulted silver particles can be easily recovered, while the only other byproduct is water. This new procedure is compatible with various functional groups and proceeds under mild reaction conditions.

Oxidative Coupling of Aromatic Amines and Nitrosoarenes: Iodine-Mediated Formation of Unsymmetrical Aromatic Azoxy Compounds

I2/DABCO (iodine/1,4-diazabicyclo[2.2.2]octane)-mediated oxidative coupling of nitrosobenzenes with aromatic amines was revealed to lead to the production of unsymmetrical aromatic azoxy compounds, instead of azo compounds reported previously in Mills reaction. Our study illustrates that various aromatic amines can be efficiently coupled with nitrosobenzenes to produce unsymmetrical azoxy product, in which more than thirty unsymmetrical azoxybenzenes have been successfully prepared. The applicability to a broad range of substrates, scalability to large scales and mild reaction conditions make this new synthetic protocol very practical, providing a convenient and direct access to unsymmetrical azoxybenzenes. (Figure presented.).