2 6-DIFLUORO-4-METHOXYPHENYLBORONIC ACID Chemical Properties

Melting point:

125-130 °C(lit.)

Boiling point:

269.3±50.0 °C(Predicted)

Density 

1.35±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

8.55±0.58(Predicted)

color 

White to Almost white

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2931900090

2 6-DIFLUORO-4-METHOXYPHENYLBORONIC ACID Usage And Synthesis

Uses

suzuki reaction

Uses

2,6-Difluoro-4-methoxyphenylboronic acid can be used:

• To prepare a ligand N4Py^2Ar2, which in turn is used to synthesize a Fe complex, employed in aromatic C?F hydroxylation reactions.
• As a substrate in the study of copper-catalyzed trifluoromethylthiolation of boronic acids.
• As a substrate in the preparation of a thio xylopyranoside as a potent antithrombotic agent.

Synthesis

General procedure for the synthesis of 2,6-difluoro-4-methoxyphenylboronic acid from 2-(3,5-difluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) anisole: To an acetone solution of 2,6-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) anisole (0.88 g. 15 mL) was added to an aqueous ammonium acetate solution (18 mL, 1 mol/L aqueous solution) and sodium metaiodate (2.6 g). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the mixture was concentrated, diluted with water and extracted with ethyl acetate. The organic phases were combined, dried with sodium sulfate and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography with the eluent cyclohexane/ethyl acetate (1:0→1:1). The target product 2,6-difluoro-4-methoxyphenylboronic acid was obtained in a yield of 0.27 g in 44%.

References

[1] Patent: WO2008/34859, 2008, A1. Location in patent: Page/Page column 40

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