Tetrabromodiphenyl ethers (CHEM001782)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (6)XML
Record Information
Version1.0
Creation Date2009-06-24 17:25:21 UTC
Update Date2026-03-26 19:31:09 UTC
Accession NumberCHEM001782
Identification
Common NameTetrabromodiphenyl ethers
ClassSmall Molecule
DescriptionPersistent environmental pollutants, detected in fish and human breast milk. Tetrabromodiphenyl ethers is present in land-applied sewage sludge.
Contaminant Sources
  • FooDB Chemicals
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Aromatic Hydrocarbon
  • Bromide Compound
  • Ether
  • Food Toxin
  • Metabolite
  • Organic Compound
  • Organobromide
  • Pollutant
  • Polybrominated Biphenyl
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC12H6Br4O
Average Molecular Mass485.791 g/mol
Monoisotopic Mass481.715 g/mol
CAS Registry Number40088-47-9
IUPAC Name1,2,3-tribromo-4-(3-bromophenoxy)benzene
Traditional Name1,2,3-tribromo-4-(3-bromophenoxy)benzene
SMILESBrC1=CC(OC2=C(Br)C(Br)=C(Br)C=C2)=CC=C1
InChI IdentifierInChI=1S/C12H6Br4O/c13-7-2-1-3-8(6-7)17-10-5-4-9(14)11(15)12(10)16/h1-6H
InChI KeyVIHUMJGEWQPWOT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as bromodiphenyl ethers. Bromodiphenyl ethers are compounds that contain two benzene groups linked to each other via an ether bond, and where at least one ring is substituted with a bromo group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylethers
Direct ParentBromodiphenyl ethers
Alternative Parents
Substituents
  • Bromodiphenyl ether
  • Diaryl ether
  • Phenoxy compound
  • Phenol ether
  • Halobenzene
  • Bromobenzene
  • Aryl halide
  • Aryl bromide
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organobromide
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00018 g/LALOGPS
logP6.38ALOGPS
logP6.55ChemAxon
logS-6.4ALOGPS
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity82.79 m³·mol⁻¹ChemAxon
Polarizability31.56 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000900000-8cdb5f72db684973ea8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000900000-e035323fe6cd6984da2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1103900000-f966a6ca870fc7abdda7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000900000-57ed240262b403867f45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000900000-3a78ad9d8a76b44af69cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fc0-1419800000-7713b917d4f071476fc5Spectrum
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3) ; dermal (3)
Mechanism of ToxicityLike other halogenated aromatic hydrocarbons, polybrominated diphenyl ethers bind to the cellular aryl hydrocarbon receptor (AhR), which regulates the synthesis of a variety of proteins. Activation of the AhR induces a number of enzymes, including cytochrome P-450-dependent monooxygenases of the CYP1A and CYP2B families, UDP-glucuronosyltransferase, and ethoxyresorufin-o-deethylase. PBDEs are also believed to disrupt the production, transport, and disposition of thyroid hormones. One mechanism of this involves metabolites ot PDBEs competing with thyroxine to bind to transthyretin, decreasing serum thyroid hormone levels. This change in thyroid hormone levels has been linked to both thyroid toxicity and neurobehavioral alterations. Certain PDBEs and their metabolites are also endocrine disruptors and may act as agonists at the estrogen receptors or antagonists at the androgen and progesterone receptors. (3, 1)
MetabolismPolybrominated biphenyls can be absorbed through oral, inhalation, and dermal routes. Once in the body they distribute throughout and bioaccumulate in the blood, breast milk, and adipose tissue. The extent of PBDE metabolism depends on the degree of bromination. Metabolism is believed to involve debromination and methylation, resulting in phenolic metabolites. Metabolized and unmetabolized PDBE compounds are excreted mainly in the faeces. (3, 4)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesPolybrominated diphenyl ethers (PBDEs) are flame-retardant chemicals found in plastics used in a variety of consumer products to make them difficult to burn. Because they are mixed into plastics and foams rather than bound to them, PBDEs can leave the products that contain them and enter the environment. (3)
Minimum Risk LevelIntermediate Inhalation: 0.006 mg/m3 (2) Acute Oral: 0.03 mg/kg/day (2) Intermediate Oral: 0.007 mg/kg/day (2)
Health EffectsPolybrominated diphenyl ethers may affect the thyroid gland and liver. Animals studies have also shown that PDBEs can cause neurobehavioral alterations and affect the immune system. (3)
SymptomsNot Available
TreatmentEYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
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 ID22833475
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available