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2,2',3,3',5,5',6,6'-Octabromobiphenyl

HCID 154382
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Basic information

CAS
59080-41-0
Standard SMILES
Brc1cc(Br)c(Br)c(-c2c(Br)c(Br)cc(Br)c2Br)c1Br
InChIKey
IQIHDBRYKJLECA-UHFFFAOYSA-N
Molecular formula
C12H2Br8
Average molar mass
785.4 g/mol
Monoisotopic mass
777.36234686

Overview

2,2',3,3',5,5',6,6'-Octabromobiphenyl is a polybrominated biphenyl. Polybrominated biphenyls (PBBs) are a group of 209 synthetic organic compounds with 1-10 bromine atoms attached to biphenyl. They can be used as flame retardants and may be added to the plastics used to make products like computer monitors, televisions, textiles, and plastic foams to make them difficult to burn. However, the use of PBBs is banned or restricted in most areas due to their toxicity and persistence in the environment. (L628, L629)

Names & identifiers

Preferred name
2,2',3,3',5,5',6,6'-Octabromobiphenyl
IUPAC
1,2,4,5-tetrabromo-3-(2,3,5,6-tetrabromophenyl)benzene

Names & synonyms

2,3,5,6,2',3',5',6'-OctabromobiphenylUNII-C0YT48Q85IC0YT48Q85I2,2',3,3',5,5',6,6'-OctabromobiphenylDTXSID002078151,2,4,5-tetrabromo-3-(2,3,5,6-tetrabromophenyl)benzeneRefChem:197235DTXCID501303062,2',3,3',5,5',6,6'-Octabromo-1,1'-biphenyl59080-41-0PBB 2021,1'-Biphenyl, 2,2',3,3',5,5',6,6'-octabromo-
Show more names
SCHEMBL30057734NS00122320Q27275030

Database identifiers

CAS
59080-41-0
PubChem CID
154382
DTXSID
DTXSID00207815
UNII
C0YT48Q85I
Nikkaji
J1.195.593B

Properties

Computed structural properties

XLogP
9.1
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
1
Heavy atoms
20
Formal charge
0
Complexity
279

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety & protection

Minimum Risk LevelAcute Oral: 0.01 mg/kg/day (L134)

Toxicology

Treatment · 1 item

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.

Health EffectsPBB exposure may cause weight loss, skin disorders (such as acne), nervous and immune systems effects, and effects on the liver, kidneys, and thyroid gland. (L628)
Exposure RoutesOral (L628) ; inhalation (L628) ; dermal (L628)
Toxicity Summary · 1 item

The exact mechanism of toxicty of PBBs varies depending on the specific congener. The predominant interaction is believed to involve the aryl hydrocarbon receptor (AhR). PBBs bind to and activate the AhR, which in turn initiates the transcriptional upregulation of a number of genes, affecting biochemical and endocrine pathways, cell cycle regulation, morphogenesis, oxidative stress response, and various other processes. This results in the numerous toxic responses characteristic of PBBs. Some of the known induced genes include the cytochrome P-450-dependent monooxygenases CYP1A1 and CYP1A2. (L628)

Signs and SymptomsSymptoms of PBB exposure may include nausea, abdominal pain, loss of appetite, joint pain, fatigue, and weakness. (L629)

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

PBBs can be absorbed via oral, inhalation, and dermal routes. Due to their lipophilic nature, PBBs, especially the highly brominated congeners, tend to accumulate in lipid-rich tissues such as the liver, adipose, skin, and breast milk. Certain PBB compounds are metabolized by the microsomal monooxygenase system catalyzed by cytochrome P-450 of the type induced by phenobarbital. The rate of metabolism may depends on the bromine substitution pattern. PBB congeners of low bromine content are transformed into hydroxylated derivatives that are predominately eliminated in the urine. Highly brominated congeners are either retained or excreted unchanged in the feces. (L628)

Uses & manufacturing

Uses · 1 item

PBBs can be used as flame retardants and may be added to the plastics used to make products like computer monitors, televisions, textiles, and plastic foams to make them difficult to burn. However, the use of PBBs is banned or restricted in most areas due to their toxicity and persistence in the environment. (L628, L629)

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Compound notes

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Carcinogen Classification
2A, probably carcinogenic to humans. (L135)