4-ETHOXY-3-FLUOROPHENYLBORONIC ACID Chemical Properties

Melting point:

108-113 C

Boiling point:

328.1±52.0 °C(Predicted)

Density 

1.22±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

7.90±0.10(Predicted)

color 

White to Almost white

CAS DataBase Reference

279263-10-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2931900090

MSDS

• Language:English Provider:SigmaAldrich

4-ETHOXY-3-FLUOROPHENYLBORONIC ACID Usage And Synthesis

Uses

suzuki reaction

Synthesis

General procedure for the synthesis of 4-ethoxy-3-fluorophenylboronic acid from trimethyl borate and 4-bromo-2-fluorophenylethyl ether: 4-bromo-2-fluorophenylethyl ether (43.8 g) was dissolved in dry tetrahydrofuran (400 ml) and the resulting solution was cooled down to -70 °C. Under nitrogen protection, n-butyllithium (133 ml) was slowly added dropwise and the reaction was stirred at -70 °C for 2 hours. Subsequently, a dry tetrahydrofuran solution of trimethyl borate (64.8 g) was slowly added at the same temperature. The reaction solution was gradually warmed to room temperature and stirring was continued for 16 hours. Upon completion of the reaction, the reaction was quenched by the addition of 2N hydrochloric acid (200 ml) and the reaction mixture was extracted with toluene. The organic layer was washed sequentially with water and saturated aqueous sodium chloride solution and then dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give a light brown solid. Purification by recrystallization (heptane: toluene=4:1, v/v) gave colorless crystals of 4-ethoxy-3-fluorophenylboronic acid (23.9 g, yield: 65%).

References

[1] Patent: EP2484658, 2012, A1. Location in patent: Page/Page column 44

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