20244-55-7

Basic information

• Product Name: 2,4,4,6-Tetrachloro-2,5-cyclohexadien-1-one
• Synonyms: 2,4,4,6-Tetrachloro-2,5-cyclohexadien-1-one
• CAS NO: 20244-55-7
• Molecular Formula: C₆H₂Cl₄O
• Molecular Weight: 231.8915
• Mol File: 20244-55-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 350°Cat760mmHg
• Flash Point: 147.8°C
• Appearance: /
• Density: 1.66g/cm³
• Vapor Pressure: 4.53E-05mmHg at 25°C
• Refractive Index: 1.582
• CAS DataBase Reference: 2,4,4,6-Tetrachloro-2,5-cyclohexadien-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,4,6-Tetrachloro-2,5-cyclohexadien-1-one(20244-55-7)
• EPA Substance Registry System: 2,4,4,6-Tetrachloro-2,5-cyclohexadien-1-one(20244-55-7)

Safety Data

• Hazardous Substances Data: 20244-55-7(Hazardous Substances Data)

Usage

General Description

2,4,4,6-Tetrachloro-2,5-cyclohexadien-1-one, also known as TCCH, is a highly toxic and environmentally hazardous chemical compound. It is an organochlorine compound with four chlorine atoms attached to a cyclohexadienone ring. TCCH is a powerful herbicide and is used to control unwanted vegetation in agricultural and industrial settings. Its toxicity and persistence in the environment make it a concern for human health and ecological impact. Due to its potential to cause harm, TCCH is regulated and its use is restricted in many countries.

InChI:InChI=1/C6H2Cl4O/c7-3-1-6(9,10)2-4(8)5(3)11/h1-2H

Upstream product

• 320-72-9 3,5-dichlorosalicylic acid 
• 1170-02-1 ethylenediamine-N,N'-bis(2-hydroxyphenylacetic acid) 
• 7664-93-9 sulfuric acid 
• 100-66-3 methoxybenzene 
• 88-06-2 2,4,6-Trichlorophenol 
• 108-95-2 phenol 
• 321-14-2 5-chloro-2-hydroxybenzoic acid 
• 25108-09-2 2,4,6,6-tetrachloro-2,4-cyclohexadienone 
• 103-73-1 Phenetole 
• 609-23-4 2,4,6-Triiodophenol 

Downstream Products

• 118-75-2 chloranil 
• 88-06-2 2,4,6-Trichlorophenol 
• 467238-65-9 2-(2',4',6'-trichlorophenoxy)-6-chloro-1,4-dihydroquinone 
• 13331-18-5 2-phenoxy-1,4-dihydroquinone 
• 3490-49-1 2-phenoxy-1,4-benzoquinone 
• 7714-21-8 2-(2',4',6'-trichlorophenoxy)-6-chloro-1,4-benzoquinone 
• 467238-62-6 2-(2',4',6'-trichlorophenoxy)-4,4-dimethoxy-6-chlorocyclohexadien-2,5-one 

Relevant articles and documents

Investigations of the reactions of monochloramine and dichloramine with selected phenols: Examination of humic acid models and water contaminants

The phenols are an important area of investigation because they are substituents in the humic acids and are common contaminants in water. The reactivities and orientations of two common phenols (phenol and m-cresol), and some of their chlorinated intermediates with aqueous monochloroamine and dichloroamine were presented. m-Cresol was more reactive than phenol with both chlorinating agents. NH2Cl and NHCl2 showed extensive reactivity toward the phenols, even the partially chlorinated less reactive intermediates would be expected to fully chlorinate the activated positions in phenolic substituents in the humic acids.

CHLORINATION OF 2,4,6-TRICHLOROPHENOL IN ACIDIC AQUEOUS MEDIUM

The course of chlorination of 2,4,6-trichlorophenol (I) in water and approximately 20percent sulfuric and hydrochloric acids has been investigated.In all these media the reaction gives primarily 2,4,6,6-tetrachloro-2,4-cyclohexadienone (II) which is subsequently chlorinated under formation of polychlorinated alicyclic ketones or isomerized to give the more stable 2,4,4,6-tetrachloro-2,5-cyclohexadienone (III), the precursor of further arising chlorinated 1,4-benzoquinones.The ratio of the arising polychlorinated alicyclic ketones to chlorinated 1,4-benzoquinones is significantly influenced by concentration of hydrogen chloride in the reaction medium.On the basis of model experiments, the reaction mechanism of exhaustive chlorination of 2,4,6-trichlorophenol has been suggested.