Basic information
- CAS
118174-38-2- Standard SMILES
Cc1cc(Cl)cc2c1oc1cc(Cl)cc(Cl)c12- InChIKey
RPMARRQIRRJWEZ-UHFFFAOYSA-N- Molecular formula
- C13H7Cl3O
- Average molar mass
- 285.5 g/mol
- Monoisotopic mass
- 283.95624788
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
- 6-Methyl-1,3,8-trichlorodibenzofuran
- IUPAC
- 1,3,8-trichloro-6-methyldibenzofuran
Names & synonyms
6-Methyl-1,3,8-trichlorodibenzofuranMCDF6-MCDF118174-38-21FU4HF6ELFRefChem:1049753,5,12-trichloro-10-methyl-8-oxatricyclo(7.4.0.02,7)trideca-1(13),2,4,6,9,11-hexaeneAhR modulator-1115039-00-41,3,8-trichloro-6-methyldibenzofuran1,3,8-Trichloro-6-methyldibenzo[b,d]furanCHEMBL4580482
Show more names
Dibenzofuran, 6-methyl-1,3,8-trichloro-DTXSID50921594RPMARRQIRRJWEZ-UHFFFAOYSA-NAhR modulator-1?UNII-1FU4HF6ELForb1710467SCHEMBL1804174BDBM50506038
Database identifiers
- CAS
118174-38-2- PubChem CID
- 114900
- DTXSID
DTXSID50921594- ChEMBL
CHEMBL4580482- UNII
- 1FU4HF6ELF
- Nikkaji
- J385.599F
Properties
Computed structural properties
- XLogP
- 6.1
- Topological polar surface area
- 13.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 298
Experimental & physicochemical properties
Endocrine DisruptorsPotential endocrine disrupting compound
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
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
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 ClassificationNo indication of carcinogenicity (not listed by IARC). (L135)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
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)
Related reactions
1 records
Compound notes
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