2,4-Difluorophenylboronic acid Chemical Properties

Melting point:

247-250 °C (lit.)

Boiling point:

251.0±50.0 °C(Predicted)

Density 

1.35±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly)

pka

8.47±0.58(Predicted)

form 

Powder

color 

Off-white to light beige or yellow

BRN 

8616257

InChI

InChI=1S/C6H5BF2O2/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,10-11H

InChIKey

QQLRSCZSKQTFGY-UHFFFAOYSA-N

SMILES

B(C1=CC=C(F)C=C1F)(O)O

CAS DataBase Reference

144025-03-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29163990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,4-Difluorophenylboronic acid Usage And Synthesis

Chemical Properties

off-white to light beige or yellow powder

Uses

suzuki reaction

Uses

2,4-Difluorophenylboronic Acid is used as a reagent in suzuki-miyaura coupling reactions such as in the synthesis of enantiomerically pure 3,3''-bis-arylated BINOL derivatives. Also used in the synthesis of highly efficient phospherescent iridium (III) complexes which are used for light-emiiting diodes.

Synthesis

(B) A solution of trimethyl borate (25.98 g, 0.25 mol, Fluka) and 2,4-difluorophenylmagnesium bromide (0.25 mol) in tetrahydrofuran (200 mL) was added dropwise simultaneously to a reactor containing tetrahydrofuran (125 mL) over a period of 1 h under nitrogen protection, maintaining the reaction temperature at -15 °C. The reaction was carried out by stirring the reaction mixture for 15 min. After the dropwise addition, the reaction mixture was continued to be stirred at -15°C for 15 minutes. Subsequently, the temperature of the reaction system was raised to 0 °C and water (17.5 mL) and 10% sulfuric acid solution (125 mL) were slowly added over 10 and 15 min, respectively. After the reaction was complete, water (250 mL) was added to ensure complete dissolution of the product, which was subsequently extracted with ether (3 x 150 mL). The organic phases were combined and concentrated to dryness under reduced pressure to afford the crude 2,4-difluorophenylboronic acid (36.98 g, 90% purity, 84.3% yield), which was used directly in the subsequent cross-coupling reaction without further purification.

References

[1] Patent: US5312975, 1994, A
[2] Patent: EP494419, 1992, A2
[3] Patent: US5312975, 1994, A
[4] Patent: EP494419, 1992, A2
[5] Patent: US2012/309971, 2012, A1. Location in patent: Page/Page column 2-3

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