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2,2',5,6'-Tetrabromobiphenyl

HCID 91669
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
60044-25-9
Standard SMILES
Brc1ccc(Br)c(-c2c(Br)cccc2Br)c1
InChIKey
IMEYSCIEAFLSQJ-UHFFFAOYSA-N
Molecular formula
C12H6Br4
Average molar mass
469.79 g/mol
Monoisotopic mass
465.7203

Overview

2,2',5,6'-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',5,6'-Tetrabromobiphenyl
IUPAC
1,3-dibromo-2-(2,5-dibromophenyl)benzene
English name
2,2',5',6-Tetrabromobiphenyl
Molecular formula
C12H6Br4
Molecular weight
469.79

Names & synonyms

60044-25-92,2',5,6'-TETRABROMOBIPHENYL2,2',5,6'-Tetrabromo-1,1'-biphenyl1,3-dibromo-2-(2,5-dibromophenyl)benzenePBB No. 538QB1542CLIPBB 531,1'-Biphenyl, 2,2',5,6'-tetrabromo-PBB 0532.2/'.5/'.6-TetrabromobiphenylUNII-8QB1542CLI2,2',5',6-TETRABROMOBIPHENYL
Show more names
PBB NO 532,2',5',6-Tetrabromo-1,1'-biphenyl
Biphenyl, 2,2',5, 6'-tetrabromo-PBB-No. 53DTXSID5074769SCHEMBL11801314SCHEMBL41756660KCA04425MFCD00152829SY475790

Database identifiers

CAS
60044-25-9
PubChem CID
91669
DTXSID
DTXSID5074769
UNII
8QB1542CLI
Nikkaji
J105.930K

Properties

Computed structural properties

XLogP
6.3
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
1
Heavy atoms
16
Formal charge
0
Complexity
223

Physicochemical properties

FDA UNII
8 QB1542CLI · 8QB1542CLI
EPA Substance Registry System
53 · PBB 053 (60044-25-9)

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)

Applications · 1 item

UsesPBB 53 is an isomer of PBB 49 (P215050), which is a related compound of PBB 37 (P215150), a brominated biphenyls that can be used as a flame retardant and often incorporated into consumer products including appliances, electronics and plastics.

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Compound notes

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