3-FLUORO-5-HYDROXYBENZENEBORONIC ACID Chemical Properties

Melting point:

54-62

Boiling point:

380.0±52.0 °C(Predicted)

Density 

1.42

storage temp. 

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

form 

powder to crystal

pka

7.23±0.10(Predicted)

color 

White to Almost white

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C6H6BFO3/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,9-11H

InChIKey

RMBFBZIEXCTPDB-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

871329-82-7

Safety Information

Hazard Note 

Harmful

HS Code 

2931900090

3-FLUORO-5-HYDROXYBENZENEBORONIC ACID Usage And Synthesis

Uses

suzuki reaction

Uses

3-Fluoro-5-hydroxybenzeneboronic acid is used as pharmaceutical intermediate.

Synthesis

Under nitrogen protection, (3-fluoro-5-methoxyphenyl)boronic acid (500 mg, 2.942 mmol) was dissolved in dichloromethane (15 mL) and cooled to 0°C. A dichloromethane solution of 1 M boron tribromide (14.7 mL, 14.7 mmol) was slowly added dropwise. The reaction mixture was stirred at room temperature for 3 h. The progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was concentrated under reduced pressure. Water (15 mL) was added to the residue and the pH was adjusted to 2 with 1 M aqueous hydrochloric acid. the product was extracted with ethyl acetate (2 x 25 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give (3-fluoro-5-hydroxyphenyl)boronic acid (430 mg) as an off-white solid.

References

[1] Patent: WO2015/58084, 2015, A1. Location in patent: Paragraph 0222

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