Basic information
- CAS
64126-86-9- Standard SMILES
Clc1cc2oc3ccccc3c2cc1Cl- InChIKey
GETJJZZRPQFSFM-UHFFFAOYSA-N- Molecular formula
- C12H6Cl2O
- Average molar mass
- 237.08 g/mol
- Monoisotopic mass
- 235.9795702
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
- 2,3-Dichlorodibenzofuran
- IUPAC
- 2,3-dichlorodibenzofuran
Names & synonyms
2,3-DICHLORODIBENZOFURAN64126-86-993W6H998EZDTXSID90214336RefChem:1059337DTXCID901368274,5-dichloro-8-oxatricyclo(7.4.0.02,7)trideca-1(13),2,4,6,9,11-hexaeneDibenzofuran, 2,3-dichloroCHEMBL139585UNII-93W6H998EZ2,3-Dichloro-dibenzofuranPCDF 12
Show more names
2,3-dichlorodibenzo[b,d]furanSCHEMBL2284587SCHEMBL2959557GETJJZZRPQFSFM-UHFFFAOYSA-NBDBM50408312DB-302233NS00121583Q27271618
Database identifiers
- CAS
64126-86-9- PubChem CID
- 47299
- DTXSID
DTXSID90214336- ChEMBL
CHEMBL139585- UNII
- 93W6H998EZ
- Nikkaji
- J460.786D
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
- 15
- Formal charge
- 0
- Complexity
- 246
Experimental & physicochemical properties
SpringerMaterials PropertiesBoiling point
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 Classification3, not classifiable as to its carcinogenicity to humans. (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
0 records
No reaction records under the current filter.
Compound notes
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