24478-72-6

Basic information

• Product Name: 1,2,3,4-TETRACHLORODIBENZOFURAN
• Synonyms: Dibenzofuran, 1,2,3,4-tetrachloro;1,2,3,4-tetrachlorodibenzo[b,d]furan
• CAS NO: 24478-72-6
• Molecular Formula: C12H4Cl4O
• Molecular Weight: 305.97156
• Mol File: 24478-72-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 168.75°C
• Boiling Point: 440.46°C (rough estimate)
• Flash Point: 205.9 °C
• Appearance: /
• Density: 1.5600 (estimate)
• Vapor Pressure: 8.96E-07mmHg at 25°C
• Refractive Index: 1.7140 (rough estimate)
• CAS DataBase Reference: 1,2,3,4-TETRACHLORODIBENZOFURAN(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-TETRACHLORODIBENZOFURAN(24478-72-6)
• EPA Substance Registry System: 1,2,3,4-TETRACHLORODIBENZOFURAN(24478-72-6)

Safety Data

• Hazardous Substances Data: 24478-72-6(Hazardous Substances Data)

Usage

Description

1,2,3,4-Tetrachlorodibenzofuran is a dioxin-like polychlorinated biphenyl (PCB) impurity that is primarily known for its presence in certain agrochemical formulations, particularly in the Japanese market. It is a toxic and persistent environmental pollutant that poses significant health risks due to its potential to accumulate in the food chain and cause adverse effects on human health and the environment.

Uses

Used in Agrochemical Formulations:
1,2,3,4-Tetrachlorodibenzofuran is used as an impurity in some agrochemical formulations, particularly in the Japanese market. Its presence in these products is a concern due to its toxic and persistent nature, which can lead to environmental contamination and potential health risks for humans and wildlife.

InChI:InChI=1/C12H4Cl4O/c13-8-7-5-3-1-2-4-6(5)17-12(7)11(16)10(15)9(8)14/h1-4H

Upstream product

• 191-07-1 Coronene 
• 2435-53-2 o-tetrachloroquinone 
• 71-43-2 benzene 
• 132-64-9 dibenzofuran 
• 227-09-8 1,2:8,9-dibenzopentacene 
• 191-24-2 Benzo[ghi]perylene 
• 190-26-1 ovalene 
• 55215-17-3 PCB 88 
• 18259-05-7 2,3,4,5,6-pentachlorobiphenyl 
• 33284-53-6 PCB 61 

Relevant articles and documents

Superacid-promoted synthesis of polychlorinated dibenzofurans

Polychlorinated dibenzofurans have been prepared in one step by the condensations of o-chloranil with arenes in triflic acid. A mechanism is proposed involving formation of a monoprotonated quinone (carboxonium ion), electrophilic attack at the arene, and cyclization of a carbocation intermediate. The chemistry is further examined by spectroscopic and theoretical studies.

Biosorption of 1,2,3,4-tetrachlorodibenzo-p-dioxin and polychlorinated dibenzofurans by Bacillus pumilus

Microbial adsorption of 1,2,3,4-tetrachlorodibenzo-p-dioxin (1,2,3,4-TCDD) and various polychlorinated dibenzofurans (PCDFs) was investigated in an effort to determine the significance of microorganisms as potential agents in transferring the molecules in the environment. The microorganisms used in this study were cultivated under low nutrient conditions for 2 months. The increase and decrease of 1,2,3,4-TCDD and PCDFs in the samples were measured by GC/MS. The peak of dibenzofuran (DBF), added as an internal standard, was compared with the peaks of 1,2,3,4-TCDD and PCDFs. The results showed that the dead biomass of microorganisms could remove these molecules from the medium more effectively than live cells. The subsequent studies suggested that the removal of the molecules be concerned with the unknown biocompound(s) of which secretion is pronounced at high temperature. UV-VIS spectrometry was used to monitor the change in the concentration of biocompound(s).

De novo synthesis mechanism of polychlorinated dibenzofurans from polycyclic aromatic hydrocarbons and the characteristic isomers of polychlorinated naphthalenes

Polychlorinated dibenzofurans (PCDFs) and polychlorinated naphthalenes (PCNs) are known to be emitted from municipal waste incinerators (MWIs) with polychlorinated dibenzo-p-dioxins (PCDDs). Two formation paths for PCDD/Fs could mainly work, which are condensation of the precursors such as chlorophenols and 'de novo' formation from carbon. However the correlation between the chemical structure of carbon and the resulting PCDD/Fs still remains unknown. In this study, the PCDD/Fs formation from polycyclic aromatic hydrocarbons (PAHs) and CuCl was examined at 400 under 10% O2. Coronene among the PAHs characteristically gave 1,2,8,9-T4CDF and the derivatives. These isomers clearly indicate that chlorination causes the cleavage of the C-C bonds in a coronene molecule and also that oxygen is easily incorporated from its outside to form 1,2,8,9-T4CDF. The symmetrical preformed structures in the coronene molecule enabled to amplify the de novo formation of the isomer. PCNs are also formed directly from these PAHs. Since there have been few reports on the formation mechanism of PCNs, this study will be a first step to know the whole formation paths. We also define the de novo synthesis as the breakdown reaction of a carbon matrix, since the word has been used without the precise definition.