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1,2,3,8,9-Pentachlorodibenzofuran

HCID 55134
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Basic information

CAS
83704-54-5
Standard SMILES
Clc1cc2oc3ccc(Cl)c(Cl)c3c2c(Cl)c1Cl
InChIKey
NKGLWUJPCTUDEH-UHFFFAOYSA-N
Molecular formula
C12H3Cl5O
Average molar mass
340.4 g/mol
Monoisotopic mass
337.862653

Overview

Chlorinated dibenzofurans (CDFs) are a family of chemical that contain one to eight chlorine atoms attached to the carbon atoms of the parent chemical, dibenzofuran. The CDF family contains 135 individual compounds (known as congeners) with varying harmful health and environmental effects. Of these 135 compounds, those that contain chlorine atoms at the 2,3,7,8-positions of the parent dibenzofuran molecule are especially harmful. Other than for laboratory use of small amounts of CDFs for research and development purposes, these chemicals are not deliberately produced by industry. Most CDFs are produced in very small amounts as unwanted impurities of certain products and processes utilizing chlorinated compounds. Only a few of the 135 CDF compounds have been produced in large enough quantities so that their properties, such as color, smell, taste, and toxicity could be studied. (L952)

Names & identifiers

Preferred name
1,2,3,8,9-Pentachlorodibenzofuran
IUPAC
1,2,3,8,9-pentachlorodibenzofuran
English name
1,2,3,8,9-PENTACHLORODIBENZOFURAN
Molecular formula
C12H3Cl5O
Molecular weight
340.42

Names & synonyms

1,2,3,8,9-PENTACHLORODIBENZOFURAN83704-54-5Dibenzofuran, 1,2,3,8,9-pentachloroIE3372MT2SDibenzofuran, 1,2,3,8,9-pentachloro-PCDF 96DTXSID602325673,4,5,12,13-pentachloro-8-oxatricyclo(7.4.0.02,7)trideca-1(13),2,4,6,9,11-hexaene3,4,5,12,13-pentachloro-8-oxatricyclo[7.4.0.02,7]trideca-1(13),2,4,6,9,11-hexaeneRefChem:410664DTXCID90155058809-721-2
Show more names
1,2,3,8,9-PCDF1,2,3,8,9-pentaCDF
UNII-IE3372MT2SSCHEMBL28737156SCHEMBL29617283NKGLWUJPCTUDEH-UHFFFAOYSA-N1,2,3,8,9-Pentachlorodibenzo[b,d]furanNS00123775Q27280676

Database identifiers

CAS
83704-54-5
PubChem CID
55134
DTXSID
DTXSID60232567
UNII
IE3372MT2S
EC Number
809-721-2
Nikkaji
J401.077I

Properties

Computed structural propertiesFilling in

XLogP
6.9
Topological polar surface area
13.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
18
Formal charge
0
Complexity
328

Physicochemical properties

Henry's Law Constant
2 · 2.0×100 mol/(m3Pa) at 25℃, Sa\cc (2005)
FDA UNII
3372 MT2S · IE3372MT2S
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
413 · H413-H301
Precautionary statements
264 · P264-P270-P301+P310-P321-P330-P405-P501

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P273, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxicology

Health Effects · 1 item

CDFs cause vomiting and diarrhea, anemia, more frequent lung infections, numbness and other effects on the nervous system, and mild changes in the liver. However, there were no permanent liver changes or definite liver damage found in people who ingested CDFs. (L952)

Exposure RoutesInhalation (L952) ; dermal (L952) ; oral (L952)
Toxicity Summary · 1 item

Halogenated dibenzofurans (PCDFs and PBDFs) bind the aryl hydrocarbon receptor (AhR), which increases its ability to activate transcription in the XRE (xenobiotic resoponse element) promoter region. Specifically AhR binds to the PCDF, translocates it to the nucleus and together with hydrocarbon nuclear translocator (ARNT) and xenobiotic responsive element (XRE) increases the expression of CYP1A1 and aryl hydrocarbon hydroxylase (CYP1B1). AhR signaling also increseases conversion of arachidonic acid to prostanoids via cyclooxygenase-2, alters Wnt/beta-catenin signaling downregulating Sox9 and alters signaling by receptors for inflammatory cytokines. AhR signalling also alters proteasomal degradation of steroid hormone receptors, alters cellular UVB stress response and changes the differentiation of certain T-cell subsets. The resulting AhR mediated activation and alteration leads to body weight loss, cancer and thymic atrophy (characteristic of immune and endocrine disruption) which are common toxic responses to PCDFs and related toxic halogenated aryl hydrocarbons.

Signs and SymptomsSkin and eye irritations, especially severe acne, darkened skin color, and swollen eyelids with discharge are the most obvious health effects of the CDF poisoning. (L952)
Carcinogen Classification3, not classifiable as to its carcinogenicity to humans. (L135)

Safety data

Signal word
Danger
Symbol(GHS)
GHS06
Hazard statements
H413-H301
Precautionary statements
P264-P270-P301+P310-P321-P330-P405-P501

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

No information on the metabolism of dibenzofuran in mammalian organisms was found in the available literature. The bacteria Sphingomonas, Brevibacterium, Terrabacter, and Staphylococcus auricularis degrade dibenzofuran to 2,2',3-trihydroxybiphenyl via dibenzofuran 4,4a-dioxygenase. (L952)

Uses & manufacturing

UsesCDFs are created from production of coal tar and during incineration. They are used as insecticides, in the production of PVC, and in industrial bleaching. (L952)

Applications

Uses1,2,3,8,9-Pentachlorodibenzofuran is a standard for environmental testing and research used for the study of PCDF/PCDD emissions from open combustion sources.

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