4171-33-9

Basic information

• Product Name: 2,2'-Dinitroazobenzene
• Synonyms: 2,2'-Dinitroazobenzene;Bis(2-nitrophenyl)diazene
• CAS NO: 4171-33-9
• Molecular Formula: C₁₂H₈N₄O₄
• Molecular Weight: 272.22
• Mol File: 4171-33-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2'-Dinitroazobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Dinitroazobenzene(4171-33-9)
• EPA Substance Registry System: 2,2'-Dinitroazobenzene(4171-33-9)

Safety Data

• Hazardous Substances Data: 4171-33-9(Hazardous Substances Data)

Usage

General Description

2,2'-Dinitroazobenzene is an organic compound with the molecular formula C12H8N4O4. It is a bright orange to yellow crystalline solid that is primarily used in the production of dyes. 2,2'-Dinitroazobenzene is known for its aromatic properties and is classified as a potentially hazardous chemical due to its explosive nature. It is also known to be toxic and can cause irritation to the skin, eyes, and respiratory system upon exposure. Due to its potentially harmful effects, 2,2'-Dinitroazobenzene should be handled with caution and proper safety measures should be followed when working with this compound.

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

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

Relevant articles and documents

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.

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.

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.