(4-Fluoro-2-(hydroxyMethyl)phenyl)boronic acid Chemical Properties

Melting point:

14-128°C

Boiling point:

361.2±52.0 °C(Predicted)

Density 

1.35±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

pka

8.62±0.58(Predicted)

form 

Solid

color 

White to Off-White

Safety Information

HS Code 

2931900090

(4-Fluoro-2-(hydroxyMethyl)phenyl)boronic acid Usage And Synthesis

Uses

4-Fluoro-2-(hydroxymethyl)phenylboronic Acid is a compound used in the preparation of 4,5-dihydro-1H-pyrazole derivatives as cholesterol 24 hydroxylase inhibitors.

Synthesis

GENERAL STEPS: To a solution of 2-bromo-5-fluorobenzyl alcohol (10.05 g, 49 mmol) in anhydrous ethanol (100 mL) was sequentially added NiCl2(dppp) (2.67 g, 4.9 mmol), tetrahydroxydiboron (6.62 g, 74 mmol), triphenylphosphine (0.01 mol), and N,N-diisopropylethylamine (25.7 mL. 148 mmol). The reaction system was degassed under nitrogen protection for 10 min. Subsequently, the reaction mixture was heated to reflux and stirred for 4 hours. After completion of the reaction, it was cooled to room temperature, diluted with water (100 mL) and extracted with ethyl acetate (3 × 50 mL). The organic phases were combined, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to give the crude product 4-fluoro-2-(hydroxymethyl)phenylboronic acid (6), which was used directly in the next step of the reaction. After purification by column chromatography, the target compound was obtained (yield: 62%).

References

[1] Patent: WO2017/183043, 2017, A1. Location in patent: Page/Page column 33

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