6-Methyl-1,3,8-trichlorodibenzofuran (CHEM001976)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2009-06-24 20:58:32 UTC
Update Date2026-03-27 01:22:13 UTC
Accession NumberCHEM001976
Identification
Common Name6-Methyl-1,3,8-trichlorodibenzofuran
ClassSmall Molecule
DescriptionChlorinated 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. (2)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Aromatic Hydrocarbon
  • Chlorinated Dibenzofuran
  • Dibenzofuran
  • Industrial By-product/Pollutant
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC13H7Cl3O
Average Molecular Mass285.553 g/mol
Monoisotopic Mass283.956 g/mol
CAS Registry Number118174-38-2
IUPAC Name3,5,12-trichloro-10-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),2,4,6,9,11-hexaene
Traditional Name3,5,12-trichloro-10-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),2,4,6,9,11-hexaene
SMILESCC1=C2OC3=CC(Cl)=CC(Cl)=C3C2=CC(Cl)=C1
InChI IdentifierInChI=1S/C13H7Cl3O/c1-6-2-7(14)3-9-12-10(16)4-8(15)5-11(12)17-13(6)9/h2-5H,1H3
InChI KeyRPMARRQIRRJWEZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as polychlorinated dibenzofurans. These are organic compounds containing two or more chlorine atoms attached to a dibenzofuran moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassDibenzofurans
Direct ParentPolychlorinated dibenzofurans
Alternative Parents
Substituents
  • Polychlorinated dibenzofuran
  • Benzenoid
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceColorless crystals.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0037 g/LALOGPS
logP6.12ALOGPS
logP5.48ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area13.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity70.68 m³·mol⁻¹ChemAxon
Polarizability27.49 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-cabd66fe034193211168Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0090000000-fd8e784026a2dd73357dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0090000000-7444682fc12d1f14c10bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-2581ac7995bd620f93abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-adbb70b46c7f975c7066Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0090000000-ba6301e5606d5661b5d6Spectrum
Toxicity Profile
Route of ExposureInhalation (2) ; dermal (2) ; oral (2)
Mechanism of ToxicityHalogenated 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.
MetabolismNo 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. (2)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (1)
Uses/SourcesCDFs are created from production of coal tar and during incineration. They are used as insecticides, in the production of PVC, and in industrial bleaching. (2)
Minimum Risk LevelNot Available
Health EffectsCDFs 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. (2)
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. (2)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID114900
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available