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2,2',4,4'-Tetrabromobiphenyl

HCID 181773
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
66115-57-9
Standard SMILES
Brc1ccc(-c2ccc(Br)cc2Br)c(Br)c1
InChIKey
UBJWRBZIWNERQZ-UHFFFAOYSA-N
Molecular formula
C12H6Br4
Average molar mass
469.79 g/mol
Monoisotopic mass
465.7203

Overview

2,2',4,4'-Tetrabromobiphenyl 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',4,4'-Tetrabromobiphenyl
IUPAC
2,4-dibromo-1-(2,4-dibromophenyl)benzene
English name
2,4-dibromo-1-(2,4-dibromophenyl)benzene
Molecular formula
C12H6Br4
Molecular weight
469.79

Names & synonyms

2,4-dibromo-1-(2,4-dibromophenyl)benzene2,2',4,4'-TetrabromobiphenylUNII-5PC8U9P5OZ5PC8U9P5OZ2,2',4,4'-Tetrabromo-1,1'-biphenylPBB 47DTXSID302163141,1'-Biphenyl, 2,2',4,4'-tetrabromo-RefChem:80626DTXCID3013880566115-57-9SCHEMBL11013516
Show more names
PBB No. 47
UBJWRBZIWNERQZ-UHFFFAOYSA-NNS00125586Q27262691

Database identifiers

CAS
66115-57-9
PubChem CID
181773
DTXSID
DTXSID30216314
UNII
5PC8U9P5OZ
Nikkaji
J105.924F

Properties

Computed structural properties

XLogP
6.5
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
1
Heavy atoms
16
Formal charge
0
Complexity
209

Physicochemical properties

Melting point
273 °C · 273 °C
Boiling point
413.7 · 413.7±40.0 °C(Predicted)
Density
2.14 · 2.140±0.06 g/cm3(Predicted)
FDA UNII
5 PC8U9P5OZ · 5PC8U9P5OZ

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)

Suppliers4 total

郑州汇聚化工有限公司13393710386 · [email protected]
河南普赛化工产品有限公司0371-60919097 15378766539 · [email protected]
郑州浩创新材料有限公司19139721821; 19139721821 · [email protected]
武汉创合化学有限公司15907120073 · [email protected]

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Carcinogen Classification
2A, probably carcinogenic to humans. (L135)