Basic information
- CAS
13029-09-9- Standard SMILES
Brc1ccccc1-c1ccccc1Br- InChIKey
DRKHIWKXLZCAKP-UHFFFAOYSA-N- Molecular formula
- C12H8Br2
- Average molar mass
- 312 g/mol
- Monoisotopic mass
- 309.89928
Overview
2,2'-Dibromobiphenyl 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'-Dibromobiphenyl
- IUPAC
- 1-bromo-2-(2-bromophenyl)benzene
- English name
- 2,2'-Dibromobiphenyl
- Molecular formula
- C12H8Br2
- Molecular weight
- 312
Names & synonyms
2,2'-Dibromobiphenyl13029-09-92,2'-Dibromo-1,1'-biphenyl1,1'-Biphenyl, 2,2'-dibromo-1-bromo-2-(2-bromophenyl)benzeneo,o'-DibromobiphenylBiphenyl, 2,2'-dibromo-UNII-GSL06P6P2LGSL06P6P2LPBB 4NSC 91566NSC-91566
Show more names
2,2'-DBBPBB NO 42,2-Dibromophenyl2,2'-Diromo biphenyl2,2′-dibroModiphenyl
DTXSID50747612'-Dibromo-biphenylRefChem:80700DTXCID0033966Biphenyl, 2,2'-dibromo-(8CI)1,1'-Biphenyl, 2,2'-dibromo-(9CI)625-732-3DRKHIWKXLZCAKP-UHFFFAOYSA-N
Database identifiers
- CAS
13029-09-9- PubChem CID
- 83060
- DTXSID
DTXSID5074761- ChEMBL
CHEMBL267917- UNII
- GSL06P6P2L
- EC Number
- 625-732-3
- Nikkaji
- J81.532B
Properties
Computed structural properties
- XLogP
- 5.1
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 1
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 161
Physicochemical properties
- Melting point
- 79 · 79-83 °C
- Boiling point
- 332.9 · 332.9±17.0 °C(Predicted)
- Density
- 1.667 · 1.667
- vapor pressure
- 0.007 · 0.007-0.27Pa at 20-50℃
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Acetone (Sparingly), Benzene (Sparingly), Ethyl Acetate (Slightly)
- form
- Crystalline Powder
- color
- White
- Water Solubility
- Insoluble in water.
- InChI
- InChI=1S/C12H8Br2/c13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)14/h1-8H
- InChIKey
- DRKHIWKXLZCAKP-UHFFFAOYSA-N
- SMILES
- C1(C2=CC=CC=C2Br)=CC=CC=C1Br
- LogP
- 4.6 at · 4.6 at 25℃ and pH6.2
- CAS DataBase Reference
- 13029 · 13029-09-9(CAS DataBase Reference)
- FDA UNII
- 6 P6P2L · GSL06P6P2L
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (86.7%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationREACH registered substance: 2,2'-dibromobiphenyl (EC: 625-732-3)
Hazard Classes and CategoriesAcute Tox. 4 (86.7%)
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.
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'-Dibromobiphenyl is used to produce 5,5-dimethyl-5H-dibenzosilole at the temperature of -78 - 20°C. It will need reagent n-BuLi and solvents diethyl ether, hexane.
Upstream & downstream products
Downstream products
Related reactions
7 records
Compound notes
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