4171-33-9

Usage

Uses

Used in Dye Production Industry:
2,2'-Dinitroazobenzene is used as a key intermediate in the production of dyes for various applications, including textiles, plastics, and printing inks. Its vibrant color and chemical properties make it a valuable component in the synthesis of a range of dye products.
Given the potential hazards associated with 2,2'-Dinitroazobenzene, it is crucial to implement stringent safety protocols during its production, handling, and use to minimize risks to human health and the environment.

Upstream product

• 56-23-5 tetrachloromethane 
• 59483-70-4 N,N-dichloro-2-nitroaniline 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 88-74-4 2-nitro-aniline 
• 79-11-8 chloroacetic acid 
• 67-56-1 methanol 
• 64-19-7 acetic acid 
• 71-43-2 benzene 
• 7722-84-1 dihydrogen peroxide 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 5375-50-8 N,N'-bis-(2,4-dinitro-phenyl)-hydrazine 
• 5267-25-4 bis-(2,4-dinitro-phenyl)-diazene 

Relevant academic research and scientific papers

Conversion of anilines into azobenzenes in acetic acid with perborate and Mo(VI): correlation of reactivities

Azobenzenes are extensively used to dye textiles and leather and by tuning the substituent in the ring, vivid colours are obtained. Here, we report preparation of a large number of azobenzenes in good yield from commercially available anilines using sodium perborate (SPB) and catalytic amount of Na2MoO4 under mild conditions. Glacial acetic acid is the solvent of choice and the aniline to azobenzene conversion is zero, first and first orders with respect to SPB, Na2MoO4 and aniline, respectively. Based on the kinetic orders, UV–visible spectra and cyclic voltammograms, the conversion mechanism has been suggested. The reaction rates of about 50 anilines at 20–50?°C and their energy and entropy of activation conform to the isokinetic or Exner relationship and compensation effect, respectively. However, the reaction rates, deduced by the so far adopted method, fail to comply with the Hammett correlation. The specific reaction rates of molecular anilines, obtained through a modified calculation, conform to the Hammett relationship. Thus, this work presents a convenient inexpensive non-hazardous method of preparation of a larger number of azobenzenes, and shows the requirement of modification in obtaining the true reaction rates of anilines in acetic acid and the validity of Hammett relationship in the conversion process, indicating operation of a common mechanism.

Graphene oxide supported MnO2 nanorods: An efficient heterogeneous catalyst for oxidation of aromatic amines to azo-compounds

Graphene oxide supported MnO2 nanorods (GOnc), a composite material, has been synthesized and characterized by XRD, FE-SEM, EDX, BET surface area measurement, FTIR and Raman Spectroscopy. The composite material (GOnc) was found to be a highly efficient, reusable and cost effective heterogeneous catalyst for the one-pot, selective synthesis of azo-compounds from aromatic amines under an N2 atmosphere. After completion of the reaction, the catalyst is readily recovered by filtration and can be reused at least three times without significant loss in activity. This journal is

Meso-tetraphenylironporphyrin(III) chloride catalyzed oxidation of aniline and its substituents by m-chloroperbenzoic acid

The most fascinating feature of heme-enzymes such as cytochromes P450 is their ability to carry out oxidations with high selectivity. Metalloporphyrin complexes are used as replicate compounds for cytochrome P450. A kinetic analysis has been carried out with the aim of understanding the mechanistic studies on oxidation of anilines by m-chloroperbenzoic acid catalyzed by meso-tetraphenylironporphyrin(III) chloride in aqueous acetic acid medium. The order of the reaction is found to be second order with respect to the substrate and first order with respect to the catalyst and oxidant. Product analysis proves that azobenzene is the sole product in the catalytic oxidation. The increase of [H+] in this oxidation retards the rate of the reaction. The effects of substituents on the oxidation rate are studied with 19 ortho-, meta- and para- substituted anilines at five different temperatures. The thermodynamic parameters for the oxidation have been determined and discussed. The catalysed m-chloroperbenzoic acid oxidation with substituted anilines fulfills the isokinetic relationship and Exner correlation but not to any of the linear free energy relationships. The solvent interaction also plays a major role in leading the reactivity. Based on the kinetic results and product analysis a probable mechanism is proposed.

Mechanism and reactivity in perborate oxidation of anilines in acetic acid

Perborate but not percarbonate in acetic acid generates peracetic acid on standing and the peracetic acid oxidation of anilines is fast. The oxidation with a fresh solution of perborate in acetic acid is smooth and second order but the specific oxidation rate increases with increasing [perborate]0 or [boric acid]. Perborate on dissolution affords hydrogen peroxide and a borate; the latter assists the former in the oxidation. The oxidation rates of anilines under identical conditions do not conform to any of the linear free energy relationships but the reaction rates of molecular anilines do. Perborate oxidation proceeds via two reaction paths but the overall oxidation rates of molecular anilines conform to structure reactivity relationships; the transition states do not differ significantly. Analysis of the oxidation rates of perborate and percarbonate reveals that while perborate oxidation is faster than percarbonate it is at least as selective as the latter.

Lack of linear free energy relationship: Tungsten(VI) catalyzed perborate oxidation of anilines

Operation of linear free energy relationships in tungsten(VI) catalyzed perborate oxidation was studied with 29 para-, meta- and ortho-substituted anilines. The activation parameters were calculated from k*( = rate/[substrate]2) at 35, 40, 45, 50 and 55 °C using the Erying relationship by the method of least squares. The oxidation is not isoentropic; in an isoentropic series only enthalpy of activation determines the reactivity and the isokinetic temperature is at infinity. At the isokinetic temperature all the compounds of the reaction series react at equal rate, the variation of substituent at this temperature has no influence on the free energy of activation.

Efficient Catalytic Oxidation of Primary Aromatic Amines to Azo Derivatives by Manganese(III) Tetraphenylporphyrin

The oxidation of primary aromatic amines to the corresponding azo derivatives has been observed in catalytic systems containing manganese(III) tetraphenylporphyrin and sodium periodate in the presence of heterocyclic nitrogen bases acting as axial ligands.

Oxidative Cyclizations. VIII. Mechanisms of Oxidation of ortho-Substituted Benzenamines and Improved Cyclizations by Bis(acetato-O)phenyliodine

Published reports describe the oxidative cyclization of suitable ortho-substituted arenamines to form such products as 2,1-benzisoxazoles, benzofurazan 1-oxides and benzotriazoles, by using bis(acetato-O)phenyliodine at room temperature.However, the reactions are often inconveniently slow.We now report attempts to achieve short reaction times with more powerful iodine(III) oxidants.These often failed to give cyclic products, but the results enable us to argue that the reaction competing with cyclization involves the arenaminyl cation ArN+H.When such cations are predicted to be relatively unstable, the parent arenamine can be rapidly cyclized in high yield by oxidation with bis(acetato-O)phenyliodine in boiling benzene.

Kinetics of oxidative coupling of amines Oxidation of anilines by alkaline hexacyanoferrate(III)

The reaction of anilines with alkaline hexacyanoferrate(III) gave azobenzenes.The rate of the reaction was dependent on the first powers of the concentrations of substrate and oxidant, but was independent of the concentration of alkali in the range studied (0.0025 mol l-1 to 0.025 mol l-1).The Hammett plot gave a value of ρ+ = -1.0, indicating a radical intermediate.This radical intermediate was detected by ESR spectroscopy as four sets of 1:2:1 triplets.