21232-47-3

Basic information

• Product Name: 3,3',4,4'-TETRACHLOROAZOXYBENZENE
• Synonyms: 3,3’,4,4’-tetrachloro-azoxybenzen;3,3’,4,4’-Tetrachloroazoxybenzene;3,3’,4,4’-tetrachloro-Azoxybenzene;3,4,3’,4’-Tetrachloroazoxybenzene;Azoxybenzene,3,3’,4,4’-tetrachloro-;bis(3,4-dichlorophenyl)-diazen1-oxide;bis(3,4-Dichlorophenyl)diazene-1-oxide;bis(3,4-dichlorophenyl)diazene1-oxide
• CAS NO: 21232-47-3
• Molecular Formula: C₁₂H₆Cl₄N₂O
• Molecular Weight: 336.00084
• Mol File: 21232-47-3.mol

Chemical Properties

• Boiling Point: 101.5°C (rough estimate)
• Flash Point: 239.7 °C
• Appearance: /
• Density: 1.7762 (rough estimate)
• Vapor Pressure: 1.19E-08mmHg at 25°C
• Refractive Index: 1.6200 (estimate)
• CAS DataBase Reference: 3,3',4,4'-TETRACHLOROAZOXYBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3',4,4'-TETRACHLOROAZOXYBENZENE(21232-47-3)
• EPA Substance Registry System: 3,3',4,4'-TETRACHLOROAZOXYBENZENE(21232-47-3)

Safety Data

• Hazardous Substances Data: 21232-47-3(Hazardous Substances Data)

Usage

Uses

Used in Dye Industry:
3,3',4,4'-Tetrachloroazoxybenzene is used as a dye intermediate for the production of azo dyes, which are widely used in various applications such as textiles, plastics, and printing inks. Its chemical properties make it a valuable component in the synthesis of these dyes.

InChI:InChI=1/C12H6Cl4N2O/c13-9-3-1-7(5-11(9)15)17-18(19)8-2-4-10(14)12(16)6-8/h1-6H/b18-17-

Upstream product

• 99-54-7 3,4-dichloronitrobenzene 
• 33175-34-7 N-(3,4-dichlorophenyl)-hydroxylamine 
• 14047-09-7 3,3',4,4'-tetrachloroazobenzene 
• 100-51-6 benzyl alcohol 
• 71-43-2 benzene 
• 64-17-5 ethanol 
• 95-76-1 m,p-dichloroaniline 
• 116278-64-9 C₁₁H₁₃Cl₂NO₂ 
• 823-86-9 N-(4-chlorophenyl)hydroxylamine 
• 932-98-9 1-chloro-4-nitroso-benzene 
• 141-52-6 sodium ethanolate 
• 6819-41-6 sodium n-propoxide 
• 67083-42-5 3,4-Dichloronitrosobenzene 
• 124-41-4 sodium methylate 

Downstream Products

• 71753-42-9 N,N'-bis(3,4-dichlorophenyl)hydrazine 

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.

Modulating the catalytic behavior of non-noble metal nanoparticles by inter-particle interaction for chemoselective hydrogenation of nitroarenes into corresponding azoxy or azo compounds

Aromatic azoxy compounds have wide applications and they can be prepared by stoichiometric or catalytic reactions with H2O2 or N2H4 starting from anilines or nitroarenes. In this work, we will present the direct chemoselective hydrogenation of nitroarenes with H2 to give aromatic azoxy compounds under base-free mild conditions, with a bifunctional catalytic system formed by Ni nanoparticles covered by a few layers of carbon (Ni@C NPs) and CeO2 nanoparticles. The catalytic performance of Ni@C-CeO2 catalyst surpasses the state-of-art Au/CeO2 catalyst for the direct production of azoxybenzene from nitrobenzene. By means of kinetic and spectroscopic results, a bifunctional mechanism is proposed in which, the hydrogenation of nitrobenzene can be stopped at the formation of azoxybenzene with >95% conversion and >93% selectivity, or can be further driven to the formation of azobenzene with >85% selectivity. By making a bifunctional catalyst with a non-noble metal, one can achieve chemoselective hydrogenation of nitroarenes not only to anilines, but also to corresponding azoxy and azo compounds.

Oxidation of dichloroanilines and related anilides catalyzed by iron(III) tetrasulfonatophthalocyanine

We investigated the degradation of polychlorinated pollutants, such as dichloroanilines and related anilides, catalyzed by iron(III) tetrasulfonatophthalocyanine (FePcS) with potassium monopersulfate or hydrogen peroxide as oxidant. The reaction is influenced by the positions of the two chloro-substituents and by the nature of the oxidant. The FePcS- catalyzed oxidation of 3,5-dichloroaniline with potassium monopersulfate leads to the formation of more biodegradable products (carboxylic acids) and to potentially toxic dimers (azo and azoxy compounds). The oxidation of 3,4- dichloroaniline by FePcS/H2O2 converts this pollutant into coupling products. The formation of dimers in the catalytic oxidation of dichloroanilines can be avoided by acylation of the amine function.

Competitive Base-Induced α-Elimination and Methanolysis of N-Aryl-O-pivaloylhydroxylamines

The N-aryl-O-pivaloylhydroxylamines 1a-c are quite stable in MeOH under neutral conditions, but under mildly basic conditions (0.05 M Et2NH or Et3N) they undergo rapid decomposition (t1/2 = ca. 3-5 h at 25 deg C) by two competitive processes: apparent α-elimination to generate the nitrenes 2a-c and pivalic acid and basic ester methanolysis to generate the hydroxylamines 3a-c and methyl pivalate.The nitrenes decompose into the corresponding anilines 5 and azobenzenes 7, while the hydroxylamines undergo nitrene-mediated oxidation into the corresponding azoxybenzenes 6.The mechanism of this latter process was probed by addition of excess hydroxylamine, and a mechanism for the oxidation consistent with available data (Scheme II) is proposed.It was also found that the nitrosobenzenes 8 undergo nucleophilic attack by conjugate bases 4a-c of the title compounds to produce one of the two possible isomeric nonsymmetrical azoxybenzenes.

Preparation and spectral analysis of 3,3',4,4'-tetrachloroazobenzene and the corresponding azoxy and hydrazo analogs

An efficient preparation was developed for 3,3',4,4'-tetrachloroazobenzene and the corresponding azoxy and hydrazo derivatives, based on the lithium aluminum hydride reduction of 3,4-dichloronitrobenzene. Batches were analyzed for purity by using a reverse phase high pressure liquid chromatographic method. All 3 compounds can be synthesized in gram quantities with 97-99% purity. Detailed mass, infrared, and nuclear magnetic resonance spectral analyses are presented.