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Product Details
Description |
2,2'-Dibromobiphenyl is a polybrominated biphenyl (PBB) with two bromine atoms attached to the biphenyl structure. |
Uses |
PBBs, including 2,2'-dibromobiphenyl, have historically been used as flame retardants in various materials such as plastics for electronics, textiles, and foams. However, due to their environmental persistence and toxicity, the use of PBBs is now restricted or banned in many regions. Chemically, 2,2'-dibromobiphenyl is an important intermediate in organic synthesis. It is utilized in the production of compounds like 5,5-dimethyl-5H-dibenzosilole under specific conditions involving reagents like n-BuLi and solvents such as diethyl ether and hexane. This compound also plays a crucial role in constructing the molecular frameworks of organic luminescent materials and conjugated macromolecules, participating in Suzuki coupling reactions either individually or concurrently through its bromine atoms. Additionally, 2,2'-dibromobiphenyl is employed in copper-catalyzed synthesis of carbazole derivatives through double C-N coupling reactions with amines, and in nickel-catalyzed electroreductive syntheses of triphenylenes, showcasing its versatility and importance in advanced synthetic methodologies. |
Canonical SMILES | C1=CC=C(C(=C1)C2=CC=CC=C2Br)Br |
XLogP3 | 5.1 |
Exact Mass | 311.89723 g/mol |
Monoisotopic Mass | 309.89928 g/mol |
Complexity | 161 |
An efficient Cu-catalyzed synthesis of carbazole derivatives is reported, which proceeds by double C–N coupling reactions of 2,2′-dibromobiphenyl and amines in the presence of air. …
However, only one example was reported, and the cheaper 2,2-dibromobiphenyl was … synthesis of carbazole to use the cheaper 2,2-dibromobiphenyl as substrates in the copper-…
From different 2,2′-dibromobiphenyl compounds with sterically hindered or strongly electron-donating orwithdrawing substituents, or even 3,3′-dibromo-2,2′binaphthyl, various N-…
bromobenzene
phenol
3,3'-dibromobiphenyl
4-(4-bromophenyl)bromobenzene
2,2'-dibromobiphenyl
2,3′-dibromo-1,1′-biphenyl
2-bromo-4'-bromobiphenyl
3,4’-dibromobiphenyl
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; iodine; at 289.9 ℃; for 0.0272222h; Product distribution;
|
12.5% 30.9% 16% 17% 19.3% 4.3% |
bromobenzene
2,3-dibromobenzene
2-Bromobiphenyl
2,2'-dibromobiphenyl
Conditions | Yield |
---|---|
bromobenzene; With tert.-butyl lithium; In tetrahydrofuran; at -80 ℃; for 1h; Inert atmosphere;
2,3-dibromobenzene; In tetrahydrofuran; at -50 ℃; for 2h; Inert atmosphere;
|
44% 9% |
biphenyl
1,1'-biphenyl-2,2'-diamine
2’-bromo-[1,1’-biphenyl]-2-amine
2,3-dibromobenzene
biphenyl
2-Bromobiphenyl
(2'-bromo-biphenyl-2-yl)-triphenyl-silane
bisbenzocyclobutene
CAS:28320-31-2
Molecular Formula:C<sub>15</sub>H<sub>13</sub>Br
Molecular Weight:273.17
CAS:3970-37-4
Molecular Formula:C6H3BrClNO2
Molecular Weight:236.45
Purity:99.7%