2-(Chloroacetyl)dibenzofuran (CHEM001941)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (27)XML
Record Information
Version1.0
Creation Date2009-06-24 20:57:58 UTC
Update Date2026-08-19 08:32:19 UTC
Accession NumberCHEM001941
Identification
Common Name2-(Chloroacetyl)dibenzofuran
ClassSmall Molecule
Description2-(Chloroacetyl)dibenzofuran is an exogenous organic compound with the formula C14H9ClO2 and an average molecular weight of 244.67 g/mol. It exists as a solid at room temperature. 2-(Chloroacetyl)dibenzofuran belongs to the dibenzofurans, a subclass of benzofurans within the organic compounds. This organoheterocyclic compound is associated with two protein targets: the transient receptor potential cation channel subfamily A member 1 (TRPA1) and the aryl hydrocarbon receptor (AHR). Binding to the aryl hydrocarbon receptor increases its ability to activate transcription in the XRE promoter region, which alters the expression of several genes.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Aromatic Hydrocarbon
  • Chlorinated Dibenzofuran
  • Dibenzofuran
  • Ester
  • Industrial By-product/Pollutant
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC14H9ClO2
Average Molecular Mass244.673 g/mol
Monoisotopic Mass244.029 g/mol
CAS Registry Number13067-90-8
IUPAC Name2-chloro-1-dibenzofuran-2-ylethanone
Traditional Name2-chloro-1-{8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),2,4,6,9,11-hexaen-4-yl}ethanone
SMILESClCC(=O)C1=CC=C2OC3=CC=CC=C3C2=C1
InChI IdentifierInChI=1S/C14H9ClO2/c15-8-12(16)9-5-6-14-11(7-9)10-3-1-2-4-13(10)17-14/h1-7H,8H2
InChI KeyWRIMNMMGJFHYMN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dibenzofurans. Dibenzofurans are compounds containing a dibenzofuran moiety, which consists of two benzene rings fused to a central furan ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassDibenzofurans
Direct ParentDibenzofurans
Alternative Parents
Substituents
  • Dibenzofuran
  • Aryl ketone
  • Aryl alkyl ketone
  • Benzenoid
  • Alpha-haloketone
  • Furan
  • Alpha-chloroketone
  • Heteroaromatic compound
  • Ketone
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Organic oxide
  • Alkyl chloride
  • Hydrocarbon derivative
  • 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 Solubility0.012 g/LALOGPS
logP3.56ALOGPS
logP3.25ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)15.26ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area30.21 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity66.38 m³·mol⁻¹ChemAxon
Polarizability25.12 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-6fbbe3b559e74a14a485Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1090000000-a6aa09a8518d3f306297Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2920000000-6d9439a8fcfc3b1bfd20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-7dc388a96a447dea840aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1290000000-7dc3ab5850efbecd34f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0910000000-2c757daf295ffe8b509aSpectrum
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 ID2757441
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available