2,2',3,3',4,4',5,5'-Octabromobiphenyl
Basic information
- CAS
67889-00-3- Standard SMILES
Brc1cc(-c2cc(Br)c(Br)c(Br)c2Br)c(Br)c(Br)c1Br- InChIKey
HHYHNDNRLUQCEG-UHFFFAOYSA-N- Molecular formula
- C12H2Br8
- Average molar mass
- 785.4 g/mol
- Monoisotopic mass
- 777.36234686
Overview
2,2',3,3',4,4',5,5'-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',4,4',5,5'-Octabromobiphenyl
- IUPAC
- 1,2,3,4-tetrabromo-5-(2,3,4,5-tetrabromophenyl)benzene
- English name
- octabromobiphenyl
- Molecular formula
- C12H2Br8
- Molecular weight
- 785.38
Names & synonyms
67889-00-32,2',3,3',4,4',5,5'-octabromobiphenyl1,2,3,4-tetrabromo-5-(2,3,4,5-tetrabromophenyl)benzeneC87IGK9D50RefChem:908466PBB 1942,2',3,3',4,4',5,5'-Octabromobiphenyl (PBB 194)UNII-C87IGK9D50SCHEMBL1352856DTXSID10987252MSK6429SCA88900
Show more names
2,23,34,45,5OctabroMobiphenyl2,2',3,3',4,4',5,5'-Octabromodiphenylether1,1'-Biphenyl, 2,2',3,3',4,4',5,5'-octabromo-1,1'-Biphenyl, 2,2',3,3',4,4',5,5'-octabromo-2,2’,3,3’,4,4’,5,5’-Octabrombiphenyl in Iso-octane2,2 ', 3,3', 4,4 ', 5,5' - octabromobiphenyl (BB-194)
NS000504812,3,4,5,2',3',4',5'-OctabromobiphenylQ27275315
Database identifiers
- CAS
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
- 307
Experimental & physicochemical properties
Collision Cross Section193 Ų [M]+ [CCS Type: TIMS, Method: calibration with PAHs]
Physicochemical properties
- Melting point
- 235 °C · 235 °C
- Boiling point
- 533.3 · 533.3±45.0 °C(Predicted)
- Density
- 2.763 · 2.763±0.06 g/cm3(Predicted)
- storage temp.
- Refrigerator
- solubility
- Benzene (Sparingly), Chloroform (Slightly, Heated)
- form
- Solid
- color
- White to Off-White
- InChI
- InChI=1S/C12H2Br8/c13-5-1-3(7(15)11(19)9(5)17)4-2-6(14)10(18)12(20)8(4)16/h1-2H
- InChIKey
- HHYHNDNRLUQCEG-UHFFFAOYSA-N
- SMILES
- C1(C2=CC(Br)=C(Br)C(Br)=C2Br)=CC(Br)=C(Br)C(Br)=C1Br
- FDA UNII
- 87 IGK9D50 · C87IGK9D50
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
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
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
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
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
Uses2,2'',3,3'',4,4'',5,5''-Octabromobiphenyl is a polybrominated biphenyl compound that poses toxic dangers to animals, humans and the environment. 2,2'',3,3'',4,4'',5,5''-Octabromobiphenyl is also one of the components of Firemaster FF-1, a polybrominated biphenyl fire retardant.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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