4-Bromobiphenyl Ether (CHEM001779)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (6)XML
Record Information
Version1.0
Creation Date2009-06-24 17:25:20 UTC
Update Date2026-04-03 09:14:26 UTC
Accession NumberCHEM001779
Identification
Common Name4-Bromobiphenyl Ether
ClassSmall Molecule
DescriptionMonobromodiphenyl ethers are organobromine compounds, as well as polybrominated diphenyl ethers containing one bromine atom. Polybrominated diphenyl ethers (PBDEs) are flame-retardant man-made chemicals found in plastics used in a variety of consumer products to make them difficult to burn. PBDEs exist as mixtures of similar chemicals called congeners. 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)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Bromide Compound
  • Ether
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organobromide
  • Pollutant
  • Polybrominated Biphenyl
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4-Bromodiphenyl etherChEBI
4-BromophenoxybenzeneChEBI
4-Phenoxy-1-bromobenzeneChEBI
NSC 5619ChEBI
p-(Phenoxy)bromobenzeneChEBI
p-Bromodiphenyl etherChEBI
p-BromophenoxybenzeneChEBI
p-Bromophenyl phenyl etherChEBI
p-PhenoxybromobenzeneChEBI
Phenyl (4-bromophenyl) etherChEBI
Chemical FormulaC12H9BrO
Average Molecular Mass249.103 g/mol
Monoisotopic Mass247.984 g/mol
CAS Registry Number101-55-3
IUPAC Name1-bromo-4-phenoxybenzene
Traditional Name4-bromophenyl phenyl ether
SMILESBrC1=CC=C(OC2=CC=CC=C2)C=C1
InChI IdentifierInChI=1S/C12H9BrO/c13-10-6-8-12(9-7-10)14-11-4-2-1-3-5-11/h1-9H
InChI KeyJDUYPUMQALQRCN-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 Descriptors
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 Point18.72°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0059 g/LALOGPS
logP4.42ALOGPS
logP4.24ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)-8.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity59.92 m³·mol⁻¹ChemAxon
Polarizability21.86 ųChemAxon
Number of Rings2ChemAxon
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-ccb94bcaca9d0b80b745Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-b23c30fc1fe9c51b2c27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-9830000000-b5c8ae162f83666232ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-50ccc2367b7fd815240cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-ddf1a3272a957cce65c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9630000000-9cb424bb5747191c7c75Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udj-6590000000-934e8926ce3e1d66358bSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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 ID77421
PubChem Compound ID7565
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available