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
• Article Data: 6

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

General Description

3,3',4,4'-Tetrachloroazoxybenzene, also known as TCAB, is a synthetic compound that is classified as a chlorinated azo compound. It is commonly used as a dye intermediate and in the production of azo dyes. This chemical is known to be toxic to aquatic life and can bioaccumulate in organisms, making it a concern for environmental impact. It is also considered to be a potential human carcinogen and is regulated in some countries due to its hazardous properties. Exposure to TCAB can cause irritation to the skin, eyes, and respiratory system, and it is important to handle this chemical with proper safety precautions.

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

• 67083-42-5 3,4-Dichloronitrosobenzene 
• 124-41-4 sodium methylate 
• 33175-34-7 N-(3,4-dichlorophenyl)-hydroxylamine 
• 99-54-7 3,4-dichloronitrobenzene 
• 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 
• 14047-09-7 3,3',4,4'-tetrachloroazobenzene 

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.

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.

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.