1230-85-9

Basic information

• Product Name: Diazene, bis(3-nitrophenyl)-, 1-oxide
• CAS NO: 1230-85-9
• Molecular Formula: C12H8N4O5
• Molecular Weight: 288.219
• Mol File: 1230-85-9.mol

Chemical Properties

• CAS DataBase Reference: Diazene, bis(3-nitrophenyl)-, 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Diazene, bis(3-nitrophenyl)-, 1-oxide(1230-85-9)
• EPA Substance Registry System: Diazene, bis(3-nitrophenyl)-, 1-oxide(1230-85-9)

Safety Data

• Hazardous Substances Data: 1230-85-9(Hazardous Substances Data)

Upstream product

• 99-65-0 meta-dinitrobenzene 
• 4103-30-4 3,3'-dinitroazobenzene 
• 99-09-2 3-nitro-aniline 
• 17122-21-3 1-nitro-3-nitrosobenzene 
• 97-02-9 2,4-Dinitroanilin 
• 610-31-1 1,2,4-trinitrobenzene 
• 7664-93-9 sulfuric acid 
• 64-17-5 ethanol 
• 141-78-6 ethyl acetate 
• 67-56-1 methanol 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 62-53-3 aniline 
• 1516-59-2 3-nitrophenyl azide 

Downstream Products

• 99-09-2 3-nitro-aniline 
• 150295-35-5 (3-Nitro-benzol)-(1azo4)-(2-nitro-phenol) 
• 101-13-3 3,3'-diaminoazoxybenzene 
• 4103-30-4 3,3'-dinitroazobenzene 

Relevant articles and documents

Peculiarities of the interaction of dinitrobenzenes with t-BuNHMgBr and t-BuNHLi

Reactions of m- and p-dinitrobenzenes with t-BuNHMgBr and t-BuNHLi were studied.The reactions afford azo- and azoxy-derivatives and products of nucleophilic substitution.

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.

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.

Reduction of polyfunctional aromatic nitro compounds using lithium aluminium hydride

Aromatic nitro compounds containing yet another functional group are reduced using lithium aluminium hydride in ether. The reduction of nitrobenzanilides results in preferential reduction of amide functionality while the isomeric N-(nitrophenyl) benzamides results in preferential cleavage of the amide bond. Besides, the reduction of 2,2′-dinitrodiphenyl amine 5a, reduction of (bis-2-nitroanilino) methane 5b, 2,2′ -dinitrodiphenylether 5c, 2-nitrophenyl-2′-nitrophenoxymethane 5d, 1,3-dinitrobenzene 6a, 2-nitrobenzaldoxime 6b, 2-N(2′-nitrophenylmethyl) amino benzoic acid 6c, 2-nitrophenoxymethyl phenyl ketone 6d are carried out. Nitro group is found reluctant towards reduction in some cases whereas in some others it is reduced into different extents. This points to the limitation of the suggested azo test for aromatic nitro compounds.

Investigations of a novel process to the framework of benzo[c]cinnoline

A novel synthetic process leading to the framework of benzo[c]cinnoline has been discovered and investigated. The process is composed of two separate reactions, the first of which is a partial reduction of the nitro groups of the 2,2′-dinitrobiphenyl, a process that we believe proceeds via a SET mechanism to yield the hydroxyamino and nitroso groups. In the following step the cyclization takes place under formation of the -N=N- bond. We believe that this process take place via a radical mechanism through the nitroso radical anion. The novel process affords either benzo[c]cinnoline or benzo[c]cinnoline N-oxide, both in high yields, 93% and 91%, respectively. To obtain benzo[c]cinnoline, the reaction is conducted with an alcohol as solvent and an alkoxide as the base, while for benzo[c]cinnoline N-oxide, water is used as solvent with sodium hydroxide as the base. To establish the latter procedure, statistical experimental design and multivariate modeling were utilized to reveal the response surface for the reaction and to determine the optimal conditions for the reaction. A proposal for the complex reaction mechanism is given. During the corroboration of the mechanism, a new deoxygenation reaction for converting benzo[c]cinnoline N-oxide into benzo[c]cinnoline was discovered. The reaction is conducted by treating the N-oxide with sodium ethoxide at elevated temperature to achieve near-quantitative conversion into benzo[c]cinnoline in a yield of 96%.

Anti-androgenic activity of substituted azo- and azoxy-benzene derivatives.

Substituted phenylazo and phenylazoxy compounds were systematically prepared and their anti-androgenic activity was measured in terms of (1) the growth-inhibiting effect on an androgen-dependent cell line, SC-3, and (2) the binding affinity to nuclear androgen receptor. Generally, azo/azoxy compounds showed cell toxicity, and the growth-inhibiting effects on SC-3 cells correlated with the toxicity. However, some compounds, including 4,4'-dinitroazobenzene (25), 4,4'-dimethoxyazobenzene (33), and 2,2'-dichloroazoxybenzene (47), possessed potent anti-androgenic activity without apparent cell toxicity.

Reductive carbonylation of aromatic dinitro compounds with a palladium(phenanthroline)2(triflate)2 catalyst and an aromatic carboxylic acid as cocatalyst

Reductive carbonylation of aromatic dinitro compounds to afford valuable dicarbamates proceeds at reasonable rates and with high selectivities under the influence of a Pd(phenanthroline)2(triflate)2 catalyst in combination with an aromatic carboxylic acid as cocatalyst.

Oxidation of Primary Aromatic Amines, Catalyzed by Tungsten Compounds

Treatment of o-nitroanilines and o-aminobenzoic acids with 30 percent hydrogen peroxide in the presence of Na2WO4 and H3PO4 results in selective formation of corresponding nitroso derivatives.In other cases, the products are azoxy compounds.Oxidation of anilines containing alkyl or alkoxy groups in the ortho and para positions with hydrogen peroxide in the presence of Na2WO4 and tetrabutylammonium bromide quantitatively yields corresponding nitrosobenzenes.The H2O2-Na2WO4-H3PO4 system in the presence of tetrabutylammonium bromide is proposed for preparation of nitroso derivatives from anilines containing electron-acceptor meta and para substituents.

Catalytic selective oxidation of amines with hydroperoxides over molecular sieves: Investigations into the reaction of alkylamines, arylamines, allylamines and benzylamines with H2O2 and TBHP over TS-1 and CrS-2 as the new catalyst

The liquid phase oxidation of various substituted amines with dil H2O2 and tert-butyl hydroxyperoxide (TBHP) has been investigated over titanium and chromium silicates respectively. While TS-1/H2O2 combination exhibits a remarkable activity and selectivity in the oxidation of arylamines to produce the symmetrical azoxybenzenes, CrS-2 catalyzes the selective oxidation of various substituted amines to the corresponding nitro compounds by oxidation with 70% TBHP. The nature of the reactive intermediates during the oxidation of anilines to nitrobenzenes has been established using cyclic voltammetry experiments. Further, amines possessing α C-H bonds are selectively oxidized to either oximes or the carbonyl compounds on reaction with H2O2 catalyzed by TS-1.

Measurement of carbonyl compounds as the 2,4-dinitrophenylhydrazonate anion. Reaction mechanism and an automated measurement system

The standard procedure for determining carbonyl compounds involves the addition of strong caustic alkali to 2,4-dinitrophenylhydrazones formed upon the reaction of carbonyl compounds with 2,4-dinitrophenylhydrazine (DNPH).1 In strong base, the hydrazones form a dark red anion of quinonoid structure,2 while the corresponding product from the unreacted DNPH decomposes rapidly, resulting in a low blank. The mechanism of this decomposition has never been clearly understood. In this work, we describe a photometric flow injection analyzer for the automated measurement of the carbonyl content of alcohol ethoxylate samples. A detailed study of the mechanism of the alkaline decomposition is reported. Parameters affecting the performance of the automated system were studied. The final system attained nearly equivalent responses of C2-C9 aliphatic carbonyl compounds (within ± 12%), a sample throughput of 20 h-1, a limit of detection of 0.5 mg/L>C=O, and response linearity over 2 orders of magnitude. The method was applied to industrial samples, and the results compared well with those from the manual standard method. It should be applicable for the measurement of the carbonyl content in a variety of other organic matrices.