3,5-Difluorophenylboronic acid Chemical Properties

Melting point:

210-217 °C (lit.)

Boiling point:

266.9±50.0 °C(Predicted)

Density 

1.35±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

6.46±0.10(Predicted)

form 

powder

color 

White to Orange to Green

BRN 

6800882

InChI

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

InChIKey

QWQBQRYFWNIDOC-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

156545-07-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn,F

Risk Statements 

36/37/38-20-19-11-22

Safety Statements 

26-36-33-16-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

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

3,5-Difluorophenylboronic acid Usage And Synthesis

Chemical Properties

White to beige-yellowish powder

Uses

Reactant involved in:• ;Synthesis of honokiol analogs as angiogenesis inhibitors1• ;Homo-coupling reactions2• ;Suzuki-Miyaura cross-coupling reactions3• ;Enantioselective borane reduction of trifluoroacetophenone4

Uses

suzuki reaction

Uses

3,5-Difluorophenylboronic Acid is used in the synthesis of N-thiazol-2-yl-benzamides as glucokinase (GK) activators for treatment of type 2 diabetes mellitus (T2DM).

Uses

Intermediates of Liquid Crystals

Synthesis

(1) A solution was prepared by dissolving 100 g of 3,5-difluorobromobenzene in 150 mL of tetrahydrofuran (THF) under nitrogen protection. The solution was slowly added dropwise to a mixture containing 13.85 g of magnesium shavings and 55 mL of THF at a controlled titration rate to keep the reaction system at mild reflux. (2) After the dropwise addition was completed, the reaction mixture was stirred at 40°C for 1 hour and subsequently cooled in an ice bath. (3) A solution prepared from 64.59 g of trimethyl borate dissolved in 130 mL of THF was slowly added dropwise under ice bath cooling. After completion of the dropwise addition, the ice bath was removed and the reaction mixture was continued to be stirred at room temperature for 1 hour. (4) 10% hydrochloric acid solution was added dropwise to the reaction system until the system became acidic, followed by stirring at room temperature for 30 minutes. (5) The organic layer was separated and the aqueous layer was extracted with hexane. The organic layer and hexane extract were combined and washed with saturated saline. (6) The washed organic layer was dried by adding anhydrous sodium sulfate, filtered and distilled under reduced pressure to remove the solvent to obtain 71.65 g of 3,5-difluorophenylboronic acid.

References

[1] Patent: US5521192, 1996, A
[2] Patent: US6908914, 2005, B1
[3] Patent: EP2123623, 2009, A1. Location in patent: Page/Page column 43-44
[4] Patent: US2014/275577, 2014, A1. Location in patent: Paragraph 0094

3,5-Difluorophenylboronic acid(156545-07-2)Related Product Information

• 4-Fluorobenzeneboronic acid
• 3,5-Dimethylphenylboronic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• 1,3-Difluorobenzene
• Folic acid
• Florfenicol
• 3-Fluorophenylboronic acid
• Phenylboronic acid
• EPA
• 2,3,4,5,6-PENTAFLUOROBENZENEBORONIC ACID
• Transfluthrin
• Citric acid
• Ascoric Acid
• 3,4,5-Trifluorophenylboronic acid
• (3,5-DIFLUORO-2-METHOXYPHENYL)BORONIC ACID, 97
• 2,3,5,6-TETRAFLUOROBENZENEBORONIC ACID
• 3,5-DIFLUORO-4-(HYDROXYMETHYL)PHENYLBORONIC ACID
• 3,5-DIFLUOROBENZENEBORONIC ACID NEOPENTYL GLYCOL CYCLIC ESTER