23663-92-5

Upstream product

• 186581-53-3 diazomethane 
• 582-69-4 azoxybenzene-4,4'-dicarboxylic acid 
• 67-56-1 methanol 
• 47163-83-7 4,4'-azoxydibenzoyl chloride 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 121986-07-0 p-nitromandelonitrile 
• 80466-34-8 2,4-hexadienal 
• 13170-28-0 methyl p-nitrosobenzoate 
• 555-16-8 4-nitrobenzaldehdye 
• 151-50-8 potassium cyanide 
• 62-53-3 aniline 
• 24226-29-7 N-[(4-methoxycarbonyl)phenyl]hydroxylamine 
• 74-88-4 methyl iodide 
• 7647-01-0 hydrogenchloride 

Relevant academic research and scientific papers

Continuous Flow Synthesis of Azoxybenzenes by Reductive Dimerization of Nitrosobenzenes with Gel-Bound Catalysts

In the search for a new synthetic pathway for azoxybenzenes with different substitution patterns, an approach using a microfluidic reactor with gel-bound proline organocatalysts under continuous flow is presented. Herein the formation of differently substituted azoxybezenes by reductive dimerization of nitrosobenzenes within minutes at mild conditions in good to almost quantitative yields is described. The conversion within the microfluidic reactor is analyzed and used for optimizing and validating different parameters. The effects of the different functionalities on conversion, yield, and reaction times are analyzed in detail by NMR. The applicability of this reductive dimerization is demonstrated for a wide range of differently substituted nitrosobenzenes. The effects of these different functionalities on the structure of the obtained azoxyarenes are analyzed in detail by NMR and single-crystal X-ray diffraction. Based on these results, the turnover number and the turnover frequency were determined.

Preparation of azoxy benzene (by machine translation)

[A] good workability and safety, cost, and, efficient production of the azoxy benzene azoxy benzene can be produced. [Solution] nitrobenzene ones, having the photocatalytic function with a dye, a reducing agent such as a fluorine resin or a transparent resin material is a mixed solution of 1 mm in diameter are inserted into the tube 4 does not inhibit the reaction, 4 LED lamp 5 emits visible from the outside of the tube moves within the tube 4 is provided with visible light within the tube 4 by a photocatalyst reaction mixed solution so as to obtain azoxy benzene compounds. Figure 2 [drawing] (by machine translation)

Au@zirconium-phosphonate nanoparticles as an effective catalytic system for the chemoselective and switchable reduction of nitroarenes

In the present paper, a novel inorganic-organic layered material, a zirconium phosphate aminoethyl phosphonate, ZP(AEP), bearing aminoethyl groups on the layer surface, was used to immobilize AuNPs by a two-step procedure. The gold-based catalyst, Au1@ZP(AEP), containing 1 wt% Au, was characterized in terms of physico-chemical properties and TEM analysis revealed that the AuNPs have a spherical shape and an average size of 7.8 (±2.4) nm. Au1@ZP(AEP) proved its high efficiency for the chemoselective reduction of nitroarenes under mild conditions. Both batch and flow condition protocols have been defined. The catalytic system has been proven to be able to easily switch chemoselectivity allowing the control of the reduction of a series of nitroaromatics towards their corresponding azoxyarenes (2a-k) or anilines (2a-l) in 96% EtOH or abs EtOH, respectively, by using NaBH4 as a reducing agent, in good to excellent yields. Recovery and reuse of the catalytic system has been investigated proving the benefits of the flow approach.

Mild, selective and switchable transfer reduction of nitroarenes catalyzed by supported gold nanoparticles

A highly versatile and flexible gold-based catalytic system has been developed for the controlled and selective transfer reduction of nitroarene using 2-propanol as a convenient hydrogen source under mild conditions. Depending on the specific reaction conditions, multiple products including azoxyarenes, symmetric or asymmetric azoarenes and anilines can be obtained respectively via a controlled reduction of the nitro aromatics with good to excellent yields in the presence of a reusable mesostructured ceria-supported gold (Au/meso-CeO2) catalyst. The overall operational simplicity, high chemoselectivity, functional-group tolerance and reusability of the catalyst make this approach an attractive and reliable tool for organic and process chemists. The Royal Society of Chemistry.

Nitrosobenzene as a hydrogen acceptor in rhodium catalysed dehydrogenation reactions of alcohols: Synthesis of aldehydes and azoxybenzenes

Acids, esters and amides have to date been the only isolated products from the dehydrogenation of primary alcohols with [Rh(trop2N)(L)] (trop = 5-H-dibenzo[a,d]cyclohepten-5yl) type complexes. With the reported method the available product family is finally to aldehydes. Using nitrosobenzene as a hydrogen acceptor the aldehydes could be isolated in up to 96% yield with substrate to catalyst ratios of up to 1000. Nitrosobenzene was found to be reductively coupled to azoxybenzene under the reaction conditions. Several symmetrically substituted azoxybenzene derivatives could be isolated in generally high yields after 2 to 4 h reaction time using a low catalyst loading. The Royal Society of Chemistry 2012.

Highly selective conversion of nitrobenzenes using a simple reducing system combined with a trivalent indium salt and a hydrosilane

Controlling the type of indium salt and hydrosilane enables a highly selective reduction of aromatic nitro compounds into three coupling compounds, azoxybenzenes, azobenzenes and diphenylhydrazines, and one reductive compound, anilines. The Royal Society of Chemistry 2010.

In situ generation of nitroso compounds from catalytic hydrogen peroxide oxidation of primary aromatic amines and their one-pot use in hetero-Diels-Alder reactions

A method for in situ generation of nitroso compounds from organoselenium-catalyzed oxidation of anilines by hydrogen peroxide was developed. The generated nitroso compounds were subsequently used in hetero-Diels-Alder reactions. A variety of oxazines were synthesized in reasonable to good yields by this one-pot procedure using primary aromatic amines with different substituents and various conjugated dienes. This strategy might facilitate the current methodologies for nitroso chemistry since no isolation or purification of the nitroso compounds is required. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Novel C-C bond cleavage from arylacetonitriles in alcohols to aryl carboxylic esters using potassium iodide and catalytic amount of samarium

A novel way to cleave the carbon-carbon bond from arylacetonitriles in alcohols to their corresponding aryl carboxylic esters using potassium iodide and a catalytic amount of samarium under mild and neutral conditions is described. Useful yields of the reaction can be obtained with electron-deficient subsistent groups in aromatic rings, and the yields are higher when the subsistent group is an electron-withdrawing group (EWG) rather than an electron-donating group (EDG). Products were characterized by IR, 1H NMR, 13C NMR, and MS. Copyright Taylor & Francis Group, LLC.

Aqueous manganese-mediated reductive coupling of nitroarenes to azoxybenzenes

Azoxy compounds have been prepared in good yields by reductive coupling of aromatic nitro compounds with manganese and a catalytic amount of acetic acid in aqueous conditions. Copyright Taylor & Francis Group, LLC.

Synthesis of N-arylhydroxylamines by antimony-catalyzed reduction of nitroarenes

Metallic antimony catalyzes the reduction of aromatic nitro compounds to the corresponding N-arylhydroxylamines in good yields with NaBH4 under mild conditions. The azoxybenzenes from autoxidation of N-arylhydroxylamines were also obtained in basic conditions.