13620-57-0

Basic information

• Product Name: 2,2'-DIMETHOXYAZOXYBENZENE
• Synonyms: 2,2'-DIMETHOXYAZOXYBENZENE;1-(2-Methoxyphenyl-ONN-azoxy)-2-methoxybenzene;2,2'-(ONN-Azoxy)bis(1-methoxybenzene);2,2'-(ONN-Azoxy)dianisole;2,2'-Azoxyanisole;2,2'-Azoxydianisole
• CAS NO: 13620-57-0
• Molecular Formula: C₁₄H₁₄N₂O₃
• Molecular Weight: 258.27256
• Mol File: 13620-57-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2'-DIMETHOXYAZOXYBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-DIMETHOXYAZOXYBENZENE(13620-57-0)
• EPA Substance Registry System: 2,2'-DIMETHOXYAZOXYBENZENE(13620-57-0)

Safety Data

• Hazardous Substances Data: 13620-57-0(Hazardous Substances Data)

Usage

Uses

Used in Polymer Production Industry:
2,2'-DIMETHOXYAZOXYBENZENE is used as a radical initiator for [the purpose of initiating polymerization reactions], which is essential in the production of various polymers. Its role in this process is critical for creating a wide range of polymeric materials with diverse applications.
Used in Scientific Research:
In the field of scientific research, particularly in electron paramagnetic resonance (EPR) spectroscopy, 2,2'-DIMETHOXYAZOXYBENZENE is used as a spin label for [the purpose of studying the dynamics and interactions of molecules in various environments]. This application aids researchers in gaining insights into molecular behavior and structural information that might not be accessible through other methods.

Upstream product

• 610-67-3 1-ethoxy-2-nitrobenzene 
• 124-41-4 sodium methylate 
• 88-73-3 2-Chloronitrobenzene 
• 91-23-6 2-Nitroanisole 
• 787-77-9 N,N'-bis-(2-methoxy-phenyl)-hydrazine 
• 71-43-2 benzene 
• 67-56-1 methanol 
• 90-04-0 2-methoxy-phenylamine 
• 123-91-1 1,4-dioxane 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 17075-26-2 2-nitrosoanisole 
• 35758-76-0 N-(2-methoxyphenyl)hydroxylamine 
• 64-17-5 ethanol 
• 50-99-7 D-glucose 

Downstream Products

• 1229-55-6 sudan red G 
• 613-55-8 2,2'-dimethoxyazobenzene 
• 787-77-9 N,N'-bis-(2-methoxy-phenyl)-hydrazine 
• 119-90-4 3,3'-dimethoxy-(1,1'-biphenyl)-4,4'-diamine 
• 90-04-0 2-methoxy-phenylamine 

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.

Selective Oxidation of Anilines to Azobenzenes and Azoxybenzenes by a Molecular Mo Oxide Catalyst

Aromatic azo compounds, which play an important role in pharmaceutical and industrial applications, still face great challenges in synthesis. Herein, we report a molybdenum oxide compound, [N(C4H9)4]2[Mo6O19] (1), catalyzed selective oxidation of anilines with hydrogen peroxide as green oxidant. The oxidation of anilines can be realized in a fully selectively fashion to afford various symmetric/asymmetric azobenzene and azoxybenzene compounds, respectively, by changing additive and solvent, avoiding the use of stoichiometric metal oxidants. Preliminary mechanistic investigations suggest the intermediacy of highly active reactive and elusive Mo imido complexes.

Preparation of niobium or tantalum complex and application of niobium or tantalum complex in catalyzing aromatic amine to generate oxidized azobenzene compound

The invention provides a preparation method of niobium or tantalum complex and an application of the niobium or tantalum complex in catalyzing aromatic amine to generate an oxidized azobenzene compound. The preparation method of the complex comprises A hydration oxide preparation, @timetime@ niobium oxide or tantalum oxide and strong base in 300 - 800 °C melting calcination 2 - 8h, adding water to dissolve and filter, and then adjusting pH through 4-6, suction filtration and drying. The B complex is prepared by mixing a hydrated oxide with a molar ratio 10-25: 1 with hydrogen peroxide, adding an organic acid and a cationic precursor after clarifying the solution, and evaporating and drying to obtain a niobium complex or a tantalum complex. The molar ratio @timetime@: 1-3. In the method for synthesizing the oxidized azobenzene compound by using niobium or tantalum complex as a catalyst, ethanol is used as a solvent, hydrogen peroxide is used as an oxidant, niobium complex or tantalum complex is used as a catalyst, and the addition amount is ppm.

Tandem selective reduction of nitroarenes catalyzed by palladium nanoclusters

We report a catalytic tandem reduction of nitroarenes by sodium borohydride (NaBH4) in aqueous solution under ambient conditions, which can selectively produce five categories of nitrogen-containing compounds: anilines, N-aryl hydroxylamines, azoxy-, azo- and hydrazo-compounds. The catalyst is in situ-generated ultrasmall palladium nanoclusters (Pd NCs, diameter of 1.3 ± 0.3 nm) from the reduction of Pd(OAc)2 by NaBH4. These highly active Pd NCs are stabilized by surface-coordinated nitroarenes, which inhibit the further growth and aggregation of Pd NCs. By controlling the concentration of Pd(OAc)2 (0.1-0.5 mol% of nitroarene) and NaBH4, the water/ethanol solvent ratio and the tandem reaction sequence, each of the five categories of N-containing compounds can be obtained with excellent yields (up to 98%) in less than 30 min at room temperature. This tunable catalytic tandem reaction works efficiently with a broad range of nitroarene substrates and offers a green and sustainable method for the rapid and large-scale production of valuable N-containing chemicals.

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.

A Green Chemoenzymatic Process for the Synthesis of Azoxybenzenes

An efficient chemoenzymatic process for the synthesis of azoxybenzenes was developed. A peracid was generated in situ by Novozym 435, and then a range of anilines were oxidized by the produced peracid to afford azoxybenzenes in yields ranging from 63.1 to 94.1 %. This method expands the application of lipase in organic synthesis and provides an alternative method for the synthesis of azoxybenzenes.

Unexpected observations during the total synthesis of calothrixin B-sodium methoxide as a source of hydride

During the total synthesis of calothrixin B, various novel and unexpected results were noticed such as cleavage of C-N bond in imine using sodium cyanoborohydride, sodium methoxide as a hydride source for reduction, deformylation in the presence of bromine, and deacylation using ceric ammonium nitrate (CAN). A detailed mechanism has been proposed for the unexpected results and a few of them are generalized. Temperature dependent NMR studies have been carried out for confirmation of the structure of one of the intermediates in the synthetic sequence.

Oxygen as moderator in the zinc-mediated reduction of aromatic nitro to azoxy compounds

A simple and useful protocol for the reduction of nitro arenes to their corresponding azoxy derivatives by employing zinc and NH4Cl in a mixture of [bmim][BF4] and water is described. The selective reduction of nitro to azoxy is attributed to the hitherto unknown moderating effect of oxygen on zinc metal.

Selective reduction of aromatic nitro compounds to azoxy compounds with zinc/aluminium chloride reagent

Aromatic azoxy compounds have been prepared in good yields by the selective reduction of aromatic nitro compounds with Zn/AlCl3 reagent.

An exceptionally stable Ti superoxide radical ion: A novel heterogeneous catalyst for the direct conversion of aromatic primary amines to nitro compounds

A matrix-bound superoxide radical anion, generated by treating Ti(OR)4 (R =iPr, nBu) with H2O2, is a selective heterogeneous catalyst for the oxidation of anilines to the corresponding nitroarenes with 50 % aqueous H2O2 [Eq. (1)]. Yields of 82-98 % are obtained, even with anilines bearing electron-withdrawing substituents (R = NO2, COOH).