5-Trifluoromethyl-pyridine-3-boronic acid Chemical Properties

Melting point:

300.8 °C (decomp)

Boiling point:

299.9±50.0 °C(Predicted)

Density 

1.44±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

Crystalline Powder

pka

5.90±0.10(Predicted)

color 

White to yellow

InChI

InChI=1S/C6H5BF3NO2/c8-6(9,10)4-1-5(7(12)13)3-11-2-4/h1-3,12-13H

InChIKey

SFBQNNGMEKUJAN-UHFFFAOYSA-N

SMILES

B(C1=CC(C(F)(F)F)=CN=C1)(O)O

Safety Information

HS Code 

29333999

5-Trifluoromethyl-pyridine-3-boronic acid Usage And Synthesis

Synthesis

Under nitrogen protection, 3-bromo-5-(trifluoromethyl)pyridine (2.5 g, 11.06 mmol) and triisopropyl borate (3.06 mL, 13.27 mmol) were dissolved in anhydrous tetrahydrofuran (20 mL) and cooled to -78 °C. A hexane solution of n-butyllithium (2.5 M, 4.9 mL, 12.17 mmol) was slowly added dropwise, keeping the reaction mixture stirred at -78 °C for 3 hours. Subsequently, the reaction mixture was slowly warmed to -10 °C. The reaction was quenched by addition of water (20 mL) and the tetrahydrofuran was removed by distillation under reduced pressure. The remaining aqueous phase was diluted with water (40 mL) and washed with ether (2 x 40 mL). The aqueous phase was adjusted to pH 5 with acetic acid and the resulting suspension was extracted with ethyl acetate (80 mL). The organic phase was separated, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 3-(trifluoromethyl)pyridine-5-boronic acid as a brown solid (2.022 g, 96% yield). HPLC/MS analysis: retention time 1.47 min, mass-to-charge ratio 192.1 (M+H+).

References

[1] Patent: US2014/135320, 2014, A1. Location in patent: Paragraph 0224; 0225

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