2,6-Difluorophenylboronic acid Chemical Properties

Melting point:

147-149 °C (lit.)

Boiling point:

260.1±50.0 °C(Predicted)

Density 

1.35±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in methanol.

form 

solid

pka

8.12±0.58(Predicted)

color 

White to Almost white

BRN 

8545931

InChI

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

InChIKey

DBZAICSEFBVFHL-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

162101-25-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

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

2,6-Difluorophenylboronic acid Usage And Synthesis

Chemical Properties

White to off-white crystalline powder

Uses

suzuki reaction

Uses

2,6-Difluorophenylboronic acid can be used:

• As a substrate in the model reaction of Suzuki–Miyaura coupling with?4-chloro-3-methylanisole.
• To prepare 4-bromo-2,3′,5′,6-tetrafluorobiphenyl, a key intermediate for the synthesis of 2,6-difluorinated oligophenyls applicable in organic semiconductors.
• To prepare ethyl 4-(2,6-difluorophenyl)nicotinate, a key intermediate for the synthesis of 4-phenyl pyridine based potent TGR5 agonists.

Uses

Intermediates of Liquid Crystals

Synthesis

The general procedure for the synthesis of 2,6-difluorophenylboronic acid from trimethyl borate and 1,3-difluorobenzene was as follows: 22.8 g of 1,3-difluorobenzene (Compound I) and 150 mL of anhydrous ethyl ether were added to a 500 mL dry reaction flask under nitrogen protection and the system was cooled to -78 °C. Slowly 187 mL of 1.6 M n-butyllithium hexane solution was added dropwise to the mixture. After the dropwise addition was completed, the reaction was stirred at -60 to -70 °C for 2 hours. The system was again cooled to -78°C and 60 g of trimethyl borate was slowly added dropwise, and after the dropwise addition was completed, the reaction was stirred at a controlled temperature of -50 to -60°C for 2 hours. The reaction mixture was slowly warmed to room temperature, the reaction was quenched by the addition of 200 mL of water and acidified with 36% hydrochloric acid. After recovering the organic solvent by ascending distillation, the reaction mixture was stirred at 70 to 80 °C for 6 hours. Finally, the system was cooled to crystallization, filtered and washed with cold water to afford 27.0 g of 2,6-difluorophenylboronic acid (Compound II).

References

[1] Patent: CN103819401, 2016, B. Location in patent: Paragraph 0023; 0066; 0067

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