Identification | Back Directory | [Name]
6-broMo-2,3'-bipyridine | [CAS]
106047-28-3 | [Synonyms]
6-broMo-2,3'-bipyridine 2-Bromo-6-(3-pyridyl)pyridine 2-bromo-6-(pyridin-3-yl)pyridine | [Molecular Formula]
C10H7BrN2 | [MDL Number]
MFCD11869547 | [MOL File]
106047-28-3.mol | [Molecular Weight]
235.08 |
Chemical Properties | Back Directory | [Melting point ]
70-71 °C | [Boiling point ]
150 °C(Press: 1 Torr) | [density ]
1.493±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [pka]
3.41±0.12(Predicted) |
Hazard Information | Back Directory | [Synthesis]
The general procedure for the synthesis of 6-bromo-2,3'-bipyridine from the compound (CAS: 220565-63-9) and 2,6-dibromopyridine was as follows: to a 25 mL round-bottomed flask under argon protection was added Pd(PPh3)2Cl2 (0.06 g, 2.0 mol%), 2,6-dibromopyridine (0.60 g, 2.5 mmol), and 5.0 mL of a THF solution of 4-(ethoxycarbonyl)phenyl zinc bromide (0.5 M, 2.5 mmol). The reaction mixture was stirred for 0.5 h at room temperature. Upon completion of the reaction, the reaction was quenched with saturated NH4Cl solution and subsequently extracted with ether (10 mL x 3). The organic phase was washed sequentially with saturated NaHCO3 solution, Na2S2O3 solution and brine and dried over anhydrous MgSO4. Purification by silica gel column chromatography (eluent: 10% ethyl acetate/90% heptane) afforded 0.31 g of the target product, 6-bromo-2,3'-bipyridine (3a), in 50% isolated yield as a white solid. | [References]
[1] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 1, p. 280 - 282 [2] Tetrahedron, 2010, vol. 66, # 17, p. 3135 - 3146 |
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