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1,4,9-Trichlorodibenzofuran

HCID 51119
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
70648-13-4
Standard SMILES
Clc1ccc(Cl)c2c1oc1cccc(Cl)c12
InChIKey
NVYUPBVXKLTYHV-UHFFFAOYSA-N
Molecular formula
C12H5Cl3O
Average molar mass
271.5 g/mol
Monoisotopic mass
269.940598

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
1,4,9-Trichlorodibenzofuran
IUPAC
1,4,9-trichlorodibenzofuran
English name
1,4,9-TRICHLORODIBENZOFURAN
Molecular formula
C12H5Cl3O
Molecular weight
271.53

Names & synonyms

1,4,9-TRICHLORODIBENZOFURAN70648-13-4PCDF 35B5BAW15Q70DTXSID60220929RefChem:1053139DTXCID401434203,6,13-trichloro-8-oxatricyclo(7.4.0.02,7)trideca-1(13),2,4,6,9,11-hexaeneDibenzofuran, 1,4,9-trichloroUNII-B5BAW15Q70NVYUPBVXKLTYHV-UHFFFAOYSA-N1,4,9-trichlorodibenzo[b,d]furan
Show more names
Dibenzofuran, 1,4,9-trichloro-
NS00123905Q27274398

Database identifiers

CAS
70648-13-4
PubChem CID
51119
DTXSID
DTXSID60220929
UNII
B5BAW15Q70
Nikkaji
J460.809G

Properties

Computed structural properties

XLogP
5.3
Topological polar surface area
13.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
16
Formal charge
0
Complexity
273

Physicochemical properties

Henry's Law Constant
3.5 · 3.5×10-1 mol/(m3Pa) at 25℃, Govers and Krop (1998)
FDA UNII
5 BAW15Q70 · B5BAW15Q70

Safety & regulation

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

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)

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

Uses1,4,9-Trichlorodibenzofuran is a standard used in environmental testing and research. Involved in the study waste incineration and pollutant formation concerning polychlorodibenzo-p-dioxins and dibenzofurans.

Suppliers2 total

广州顺平生物科技有限公司—
KANTO[email protected]

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