2'-FLUORO[1,1'-BIPHENYL]-2-AMINE Chemical Properties

Boiling point:

298.4±15.0 °C(Predicted)

Density 

1.161±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

2.89±0.10(Predicted)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

2'-FLUORO[1,1'-BIPHENYL]-2-AMINE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 2'-fluoro-[1,1'-biphenyl]-2-amine from 2-fluorophenylboronic acid and o-bromoaniline was as follows: to a 20 mL Schlenk tube fitted with a magnetic stirrer were added sequentially o-bromoaniline (2 mmol), 2-fluorophenylboronic acid (2.4 mmol), K2CO3 (5 mmol), 10 mL of mixed solvent [H2O, H2O- MeOH (1:1), H2O-EtOH (1:1), H2O-EG (1:1)], and 0.01 M solution of the palladium complexes PdCl2(L)2 or Pd[(L)4]Cl2 in MeOH (0.001-0.2 mol%). The reaction mixture was placed in a preheated oil bath at temperatures selected according to the solvents: 100°C for MeOH-H2O, 110°C for EtOH-H2O, 140°C for pure H2O, and 160°C for EG-H2O; and stirred under reflux conditions for the indicated times. Upon completion of the reaction, the mixture was cooled to room temperature, acidified with 5 M HCl (if desired), and subsequently diluted with 10 mL of H2O and 10 mL of Et2O (or EtOAc). The organic phase was separated and the aqueous phase was extracted with Et2O (or EtOAc) (2 x 10 mL). The organic layers were combined and washed sequentially with H2O (10 mL), saturated saline (10 mL) and dried with anhydrous Na2SO4. Finally, the ether solution was filtered briefly through a silica gel pad and the solvent was evaporated to obtain the pure product 2'-fluoro-[1,1'-biphenyl]-2-amine.

References

[1] Catalysis Communications, 2016, vol. 79, p. 17 - 20
[2] Organic Letters, 2015, vol. 17, # 6, p. 1597 - 1600