ContaminantDB: Hexabromobiphenyl Ether

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2009-06-24 17:25:21 UTC

Update Date

2026-04-05 05:05:07 UTC

Accession Number

CHEM001784

Identification

Common Name

Hexabromobiphenyl Ether

Class

Small Molecule

Description

Hexabromodiphenyl ethers are organobromine compounds, as well as polybrominated diphenyl ethers containing four bromine atoms. 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

HPV EPA Chemicals
T3DB toxins

Contaminant Type

Aromatic Hydrocarbon
Bromide Compound
Ether
Industrial/Workplace Toxin
Organic Compound
Organobromide
Polybrominated Biphenyl
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₂H₄Br₆O

Average Molecular Mass

643.584 g/mol

Monoisotopic Mass

637.536 g/mol

CAS Registry Number

36483-60-0

IUPAC Name

1,2,5-tribromo-3-(2,3,4-tribromophenoxy)benzene

Traditional Name

1,2,5-tribromo-3-(2,3,4-tribromophenoxy)benzene

SMILES

BrC1=CC(Br)=C(Br)C(OC2=C(Br)C(Br)=C(Br)C=C2)=C1

InChI Identifier

InChI=1S/C12H4Br6O/c13-5-3-7(15)10(16)9(4-5)19-8-2-1-6(14)11(17)12(8)18/h1-4H

InChI Key

YURCHLXPAGSJHU-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Bromodiphenyl 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	148-151°C
Boiling Point	Not Available
Solubility	4.08e-06 mg/mL [RAHMAN, F et al. (2001)]

Predicted Properties

Property	Value	Source
Water Solubility	7.7e-05 g/L	ALOGPS
logP	6.96	ALOGPS
logP	8.09	ChemAxon
logS	-6.9	ALOGPS
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98.04 m³·mol⁻¹	ChemAxon
Polarizability	38.34 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000009000-76cb759680fa39eed804	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0000009000-818571a8ddb92ee1d3ba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0000009000-8583188ff491ebe42fe0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000009000-496b88ed5bf59b4a3535	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0000009000-9a16f3b5a266f115abda	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0002119000-e82c31401842a4b50e1c	Spectrum

Toxicity Profile

Route of Exposure

Oral (3) ; inhalation (3) ; dermal (3)

Mechanism of Toxicity

Like 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)

Metabolism

Polybrominated 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 Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Polybrominated 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 Level

Intermediate Inhalation: 0.006 mg/m3 (2) Acute Oral: 0.03 mg/kg/day (2) Intermediate Oral: 0.007 mg/kg/day (2)

Health Effects

Polybrominated 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)

Symptoms

Not Available

Treatment

EYES: 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

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

22833472

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Hexabromobiphenyl Ether (CHEM001784)

Structure for CHEM001784: Hexabromobiphenyl Ether