794-95-6

Upstream product

• 871876-73-2 2,3-dimethyl-4-nitroso-aniline 
• 28144-70-9 anthranilic acid amide 
• 138-89-6 p-dimethylaminonitrosobenzene 
• 620-05-3 iodomethylbenzene 
• 98-09-9 benzenesulfonyl chloride 
• 100-23-2 N,N-Dimethyl-4-nitroaniline 
• 64-17-5 ethanol 
• 60-29-7 diethyl ether 
• 100-63-0 phenylhydrazine 
• 86-73-7 9H-fluorene 
• 141-52-6 sodium ethanolate 
• 13463-40-6 iron pentacarbonyl 
• 108-98-5 thiophenol 
• 142-04-1 aniline hydrochloride 

Downstream Products

• 108900-20-5 N,N'-dimethyl-2,6,N,2',6',N'-hexanitro-4,4'-azoxy-di-aniline 
• 99-98-9 4-amino-N,N-dimethylaniline 
• 6257-64-3 methyl orange 

Relevant academic research and scientific papers

A Common, Facile and Eco-Friendly Method for the Reduction of Nitroarenes, Selective Reduction of Poly-Nitroarenes and Deoxygenation of N-Oxide Containing Heteroarenes Using Elemental Sulfur

A transition metal-free, environment-friendly and practical protocol was developed either for the reduction of nitroarenes or for the deoxygenation of N-oxide containing heteroarenes. The reaction proceeded with the use of a non-toxic and cheap feedstock as elemental sulfur in aqueous methanol under relatively mild conditions. Green chemistry credentials were widely favorable compared to traditional and industrial protocols with good E-factors and a low production of waste. The strategy allowed the efficient reduction of a large variety of substituted-nitroarenes including various o-nitroanilines as well as selective reduction of various poly-nitroarenes in excellent yields with a broad substrate scope. The protocol was successfully extended to the deoxygenation of some N-oxide containing heteroarenes, like benzofuroxans, phenazine N,N'-dioxides, pyridine N-oxides, 2H-indazole N1-oxides, quinoxaline N1,N4-dioxides and benzo[d]imidazole N1,N3-dioxides. A gram-scale example for the synthesis of luminol, in green conditions, was reported. A solid mechanism of reaction was proposed from experimental evidences.

Synthesis of Azoxybenzenes by Reductive Dimerization of Nitrosobenzene

Herein we report an effective and simple preparation method of substituted azoxybenzenes by reductive dimerization of nitrosobenzenes. This procedure requires no additional catalyst/reagent and can be applied to substrates with a wide range of substitution patterns.

Ruthenium nanoparticle-catalyzed, controlled and chemoselective hydrogenation of nitroarenes using ethanol as a hydrogen source

This communication describes a ruthenium nanoparticle-catalyzed reduction of nitroarenes giving azoxyarenes, azoarenes, or anilines in good to excellent yields using ethanol as a hydrogen source. Copyright

N,N,N′,N′-tetraalkylaminoazoxybenzene derivatives; convenient synthesis and mechanistic study

N,N,N′,N′-tetraalkyaminoazoxybenzene derivatives were conveniently prepared by the coupling of N,N-dialkylnitrosoaniline in the presence of acetone and KOH. The reaction mechanism was proposed and investigated, and the structure of compound 3b was also confirmed by single crystal X-ray diffractometry.

Nitrenium ions. ? reactions of N,N-dimethyl-p-benzoyloxyaniline-iminium chloride with indoles and indolizines. X-ray structure of unexpected [2-chloro-4-(4-dimethylaminophenyl-ONN-azoxy)-phenyl]dimethylamine (azoxy derivative)

N,N-Dimethyl-p-nitrosoaniline reacts with benzoyl chloride affording a complex salt containing a cation, a hybrid between a nitrenium ion and an iminium ion. The salt reacts with nucleophiles (indoles, indolizines) yielding compounds characterized by a new carbon-nitrogen bond, derived from the nitrenium ion form. According to the type of nucleophile, the reaction, to differing extents, is in competition with an electron transfer process which leads to the formation of the dimer of the nucleophile and of the azoxy corresponding to the N,N-dimethyl-p-nitrosoaniline. In one of the reactions studied, a chlorinated azoxy derivative was also isolated, and its structure was elucidated by X-ray analysis.

Metathesis and reduction reactions of nitroso compounds with metal carbenes and metal carbonyls

Reaction of nitroso compounds with metal-carbene complexes and metal carbonyls has been investigated.These reactions lead to reduction of the nitroso compounds, primarily to the corresponding azo- and azoxy compounds.Metal-nitrene complexes have been proposed as intermediates in these reactions.These intermediates couple rapidly with the unreacted nitroso compound, or enter into nitrene-like reactions with external or internal trapping agents.Reaction of metal carbonyls with nitrosoarenes and photolysis has been found to be an effective method for the reduction of nitrosoarenes to azoxyarenes, with few problems resulting from overreduction to amines or azo compounds.

The synthesis of anilines or azoxybenzenes from the reduction of nitrobenzenes in basic alcoholic media

Reduction of substituted nitrobenzenes in alkaline alcoholic solutions affords, depending on the experimental conditions used, either anilines or azoxybenzenes in good yields.In the presence of a methylketone, such as acetophenone, the reaction of nitroarenes with aqueous KOH in 2-propanol provides the corresponding anilines in high yields (80-90 percent).On the other hand, when the reaction is carried out in the CH3OH/toluene/KOH system, in the absence of methylketones, the azoxyderivatives are isolated in 70-90 percent yield.