Description
2-Bromobiphenyl is an important intermediate, which can be used to synthesize 2,2'-dibromo-9,9'-spirobifluorene, 3-bromo-9-(9-phenylfluoren-9-yl)carbazole and phenanthrene compounds.
Uses
2-Bromobiphenyl can be used as reference compound to investigate extraction efficiency of solid-phase microextraction fibers, based on methacrylic acid-trimethylolpropanetrimethacrylate copolymers.
synthesis
Carry out all catalytic reactions in reaction vessels open to the air.
Charge a round-bottom flask with the newly purchased or freshly
recrystallized aryl boronic acid (2.0 mmol), 1,2-dibromobenzene,
powdered K3PO4 (2.2 mmol) and toluene (2.5 mL) of
technical quality. Stir the mixture vigorously. Heat the mixture to 80
°C for 10 minutes. Add (0.2 mol%) of catalyst by syringe as a 2.5 ml of
toluene solution to the mixture. Take the samples periodically from the
reaction mixture. Quench the reaction with water. Extract the mixture
with ethyl acetate. Analyze the reaction by GC-MS. At the end of
catalytic reaction, cool the reaction mixture to room temperature.
Quench the mixture with water (adjusted to an appropriate pH when
biaryls with acidic or basic groups has to be extracted). Extract the
mixture with ethyl acetate (3×40 mL). Dry the combined extracts (MgSO4). Evaporate the combined extracts to dryness. Purify the crude material by flash chromatography on silica gel.
Physical properties
2-Bromobiphenyl has a melting point of 1.5-2 °C, so it is a colorless
liquid at room temperature. It boils at 297-298 °C. Its density at 25℃
is 1.352 g/mL. In general, 2-bromobiphenyls are stable, but they are
not compatible with oxidants.
Uses
It is used as an intermediate of organic synthesis and pharmaceutical. It also can react with norborn-2-ene to get 5-phenyl-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene, in synthesis of a novel trispirocyclic hydrocarbon. It is used as a reference compound to investigate extraction efficiency of solid-phase micro extraction fibers, based on methacrylic acid-trimethylolpropanetrimethacrylate copolymers.
General Description
Clear liquid. Insoluble in water.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
2-Bromobiphenyl is sensitive to light. Low reactivity.
Fire Hazard
Flash point data for 2-Bromobiphenyl are not available. 2-Bromobiphenyl is probably combustible.
References
[1] Tetrahedron Letters, 2014, vol. 55, # 45, p. 6180 - 6183
