21650-71-5

Upstream product

• 100-25-4 para-dinitrobenzene 
• 100-01-6 4-nitro-aniline 
• 13921-68-1 β-p-nitroazoxybenzene 
• 88867-70-3 C₁₁H₁₄N₂O₄ 
• 1516-60-5 4-nitrophenyl azide 
• 4485-08-9 4-nitrosonitrobenzene 
• 121-69-7 N,N-dimethyl-aniline 
• 768-94-5 1-Adamantanamine 
• 75-64-9 tert-butylamine 
• 16169-16-7 4-Nitro-N-phenylhydroxylamine 
• 136696-42-9 2-acetyl-3,4-dimethylthiazolium triflate 
• 7697-37-2 nitric acid 
• 3646-57-9 bis(4-nitrophenyl)diazene 
• 7732-18-5 water 

Downstream Products

• 3646-57-9 bis(4-nitrophenyl)diazene 
• 22719-28-4 4,4′-dinitrohydrazobenzene 
• 538-41-0 4,4'-Diaminoazobenzene 
• 81709-94-6 (4Z)-7-<1,2-Bis(4-nitrophenyl)-2,3,3a,4,5,8,9,9a-octahydro-1H-trans-cyclooctapyrazol-3-yl>-4-heptenal 
• 81709-92-4 7-<1,2-Bis(4-nitrophenyl)decahydro-1H-trans-cyclooctapyrazol-3-yl>heptanal 

Relevant academic research and scientific papers

Photoanalogues of the initiation substrates of the RNA polymerase II, 5-azido-2-nitrobenzoyl derivatives of the ATP γ-amidophosphate: The possible photoinduced degradation of the functional group to an n-arylhydroxylamine

Photoanlogues of the initiation substrates of the RNA polymerase II, N 3Ar-NH(CH2)nNHpppA where N3Ar is 5-azido-2-nitrobenzoyl group (n=2 or 4) were synthesized, allowing the preparation of photoreactive oligonu

Efficient and Selective Oxidation of Aromatic Amines to Azoxy Derivatives over Aluminium and Gallium Oxide Catalysts with Nanorod Morphology

Aluminium oxide and gallium oxide nanorods were identified as highly efficient heterogeneous catalysts for the selective oxidation of aromatic amines to azoxy compounds using hydrogen peroxide as environmentally friendly oxidant. This is the first report of the selective oxidation of aromatic amines to their azoxy derivatives without using transition metal catalysts. Among the tested transition-metal-free oxides, gallium oxide nanorods with small dimensions (9–52 nm length and 3–5 nm width) and fully accessible, high surface area (225 m2 g?1) displayed the best catalytic performance in terms of substrate versatility, activity and azoxybenzene selectivity. Furthermore, the catalyst loading, hydrogen peroxide type (aqueous or anhydrous), and the amount of solvent were tuned to optimise the catalytic performance, which allowed reaching almost full selectivity (98 %) towards azoxybenzene at high aniline conversion (94 %). Reusability tests showed that the gallium oxide nanorod catalyst can be recycled in consecutive runs with complete retention of the original activity and selectivity.

Low-temperature catalytic oxidation of aniline to azoxybenzene over an Ag/Fe2O3 nanoparticle catalyst using H2O2 as an oxidant

An in situ modified hydrothermal synthesis of Ag/Fe2O3 nanoparticles (NPs) and studies of their catalytic activity as a simple, eco-friendly and recyclable catalyst for one-pot conversion of aniline to azoxybenzene were performed. The as-synthesized nanostructured material was characterised by powder X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), SEM-mapping, temperature-programmed reduction (H2-TPR), X-ray photoelectron spectroscopy (XPS), N2 adsorption-desorption isotherms (BET), Fourier transform infrared spectroscopy (FT-IR), inductively coupled plasma-atomic emission spectroscopy (ICP-AES), ultraviolet-visible spectroscopy (UV-vis) and vibrating sample magnetometer spectroscopy (VSM). The most active and recyclable catalyst with 2-5 nm diameters of the metallic Ag particles supported on 10-50 nm Fe2O3 nanoparticles was formed with a silver loading of 1.8 wt%. A high turnover number of ～592 was achieved with 92% conversion of aniline and 94% selectivity towards the target product azoxybenzene under atmospheric conditions. The effects of various reaction parameters including the reaction time, temperature and substrate to H2O2 molar ratio were screened and studied in detail. The results reveal the role of a synergistic effect between the surface Ag nanoparticles and Fe2O3 nanospheres for high catalytic activity.

Nb2O5 supported on mixed oxides catalyzed oxidative and photochemical conversion of anilines to azoxybenzenes

The synthesis of novel supported niobium oxide catalysts and their application for aniline conversion to azoxybenzenes is described. The catalysts were successfully prepared by thermal decomposition of layered double hydroxides (LDHs), containing M2+ (M = Mg2+ and/or Zn2+) and Al3+ as layer cations, followed by niobium oxide incorporation employing the wetness impregnation method. These catalysts were fully characterized by both experimental techniques and theoretical calculations, and then successfully applied to the selective conversion of anilines into azoxybenzene derivatives, with up to 98% conversion and 92% isolated yield in the presence of violet light. Control experiments and DFT calculations revealed that the catalyst has a dual role in this transformation, acting both as a Lewis acid in the oxidative step and as a photocatalyst in the dimerization of the nitrosobenzene intermediate.

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.

Aromatic amine oxidation process for preparing aromatic liquid discharge method

The invention relates to a preparation method for aromatic-azoxybenzene by oxidizing aromatic amine. According to the method, air or oxygen is used as an oxygen source, and aromatic amine is oxidized to be aromatic-azoxybenzene under the effect of metal oxide catalyst. The method has the advantage of high product yield and is easy to separate the catalyst.

Organocatalytic oxidation of substituted anilines to azoxybenzenes and nitro compounds: Mechanistic studies excluding the involvement of a dioxirane intermediate

An organocatalytic and environmentally friendly approach for the selective oxidation of substituted anilines was developed. Utilizing a 2,2,2-trifluoroacetophenone-mediated oxidation process, substituted anilines can be transformed into azoxybenzenes, while a simple treatment with MeCN and H2O2 leads to the corresponding nitro compounds, providing user-friendly protocols that can be easily scaled up. Various substitution patterns and functional groups were tolerated leading to products in high to excellent yields. Mechanistic studies utilizing HRMS provide clear evidence for the distinct mechanistic intermediates that are involved. This study constitutes an indirect proof excluding the involvement of a dioxirane intermediate in the green organocatalytic oxidation, utilizing 2,2,2-trifluoroacetophenone as the catalyst.

Room temperature selective oxidation of aniline to azoxybenzene over a silver supported tungsten oxide nanostructured catalyst

Heterogeneous catalysts comprising silver nanoparticles supported on nanostructured tungsten oxide were applied for room temperature oxidative coupling of aniline to azoxybenzene, an important chemical intermediate and a chemical of industrial interest. The catalytic protocol features high activity and selectivity to the target product azoxybenzene with a turnover number of ～368. The catalyst was characterized by XRD, XPS, ICP-AES, FT-IR, TGA, EXAFS, SEM and TEM. The silver-tungsten nanomaterial acts as an excellent catalyst for selective oxidation of aniline to azoxybenzene using H2O2 as an oxidant. An aniline conversion of 87% with 91% selectivity of azoxybenzene was achieved without the use of any external additives. Moreover, a high stability and recyclability of the catalyst is also observed under the investigated conditions. This journal is

Ultrasound-accelerated selective oxidation of primary aromatic amines to azoxy derivatives with trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane catalyzed by Preyssler acid-mediated nano-TiO2

Preyssler-type heteropolyacid supported on TiO2 nanoparticles has been explored as an efficient catalyst in selective oxidation of primary aromatic amines to azoxy derivatives using trans-3,5-dihydroperoxy-3,5-dimethyl- 1,2-dioxolane as oxidant. The reactions proceeded smoothly under mild and green ultrasound-accelerated conditions to afford the products in high yields. The catalyst recovered from the reaction mixture exhibits long-term stability with no significant drop in its catalytic activity. Graphical abstract: [Figure not available: see fulltext.].

Gold-catalyzed cyclization/oxidative [3+2] cycloadditions of 1,5-enynes with nitrosobenzenes without additional oxidants

Golden control: The title reaction (see scheme) proceeds with high stereocontrol to generate the heterocyclic products in good yield. Experiments to probe the mechanism were performed. Copyright