2,2',4,5,5'-Pentabromobiphenyl
Basic information
- CAS
67888-96-4- Standard SMILES
Brc1ccc(Br)c(-c2cc(Br)c(Br)cc2Br)c1- InChIKey
OELBLPCWLAWABI-UHFFFAOYSA-N- Molecular formula
- C12H5Br5
- Average molar mass
- 548.7 g/mol
- Monoisotopic mass
- 543.63081
Overview
2,2',4,5,5'-Pentabromobiphenyl 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',4,5,5'-Pentabromobiphenyl
- IUPAC
- 1,2,4-tribromo-5-(2,5-dibromophenyl)benzene
- English name
- 2,2',4,5,5'-Pentabromobiphenyl
- Molecular formula
- C12H5Br5
- Molecular weight
- 548.69
Names & synonyms
2,2',4,5,5'-PENTABROMOBIPHENYLPBB 1011,1'-Biphenyl, 2,2',4,5,5'-pentabromo-1,2,4-tribromo-5-(2,5-dibromophenyl)benzeneUNII-03SL1NG15Q03SL1NG15Q2,4,5,2',5'-Pentabromo-1,1'-biphenyl2,2',4,5,5'-Pentabromo-1,1'-biphenylDTXSID50218113RefChem:80632DTXCID7014060467888-96-4
Show more names
PBB NO 1012,2',4,5,5'-2,2',4,5,5'-PentanbromobiphenylPBB No. 101 10 μg/mL in Cyclohexane2,2 ', 4,5,5' - pentabromobiphenyl (BB-101)
1,1'-Biphenyl,2,2',4,5,5'-pentabromo-2,2',4,5,5'-Pentabromobiphenyl (PBB 101)Biphenyl, 2,2',4,5,5'-pentabromo-PBB-No. 101MSK6418SCA88896PBB-No. 101 10 |Ig/mL in CyclohexaneNS00124004
Database identifiers
- CAS
67888-96-4- PubChem CID
- 49996
- DTXSID
Properties
Computed structural properties
- XLogP
- 7.1
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 1
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 259
Experimental & physicochemical properties
LogP7.1
Collision Cross Section172.6 Ų [M]+ [CCS Type: TIMS, Method: calibration with PAHs]
Physicochemical properties
- Boiling point
- 403.74 °C · 403.74°C (rough estimate)
- Density
- 2.4848 · 2.4848 (rough estimate)
- refractive index
- 1.704 · 1.7040 (estimate)
- Water Solubility
- 0.4423 ug/L · 0.4423ug/L(25 ºC)
- FDA UNII
- 3 SL1NG15Q · 03SL1NG15Q
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
UsesPBB 101 is a brominated biphenyls that can be used as a flame retardant and often incorporated into consumer products including appliances, electronics and plastics.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…