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2,3,3',4,4'5,6-Heptabromobiphenyl

HCID 133255
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Basic information

CAS
79682-25-0
Standard SMILES
Brc1ccc(-c2c(Br)c(Br)c(Br)c(Br)c2Br)cc1Br
InChIKey
RKSHLITXOOZMAV-UHFFFAOYSA-N
Molecular formula
C12H3Br7
Average molar mass
706.5 g/mol
Monoisotopic mass
699.45184

Overview

2,3,3',4,4',5,6-Heptabromobiphenyl 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
2,3,3',4,4'5,6-Heptabromobiphenyl
IUPAC
1,2,3,4,5-pentabromo-6-(3,4-dibromophenyl)benzene
English name
2,3,3',4,4'5,6-heptabromobiphenyl
Molecular formula
C12H3Br7
Molecular weight
706.49

Names & synonyms

Heptbbp1,1'-Biphenyl, 2,3,3',4,4',5,6-heptabromo-U9UZA0PF5F79682-25-02,3,3',4,4'5,6-Heptabromobiphenyl2,3,3',4,4',5,6-HeptabromobiphenylDTXSID60747541,2,3,4,5-pentabromo-6-(3,4-dibromophenyl)benzeneRefChem:81174DTXCID3048150UNII-U9UZA0PF5F2,3,3',4,4',5,6-heptabromo-1,1'-biphenyl
Show more names
PBB 1902,3,3',4,4',5,6-heptabromobi-phenylNS00125026Q27290970

Database identifiers

CAS
79682-25-0
PubChem CID
133255
DTXSID
DTXSID6074754
UNII
U9UZA0PF5F
Nikkaji
J1.304.086I

Properties

Computed structural properties

XLogP
8.4
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
1
Heavy atoms
19
Formal charge
0
Complexity
296

Physicochemical properties

FDA UNII
9 UZA0PF5F · U9UZA0PF5F
EPA Substance Registry System
1 · 1,1'-Biphenyl, 2,3,3',4,4',5,6-heptabromo- (79682-25-0)

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)