2,3-Difluorophenylboronic acid Chemical Properties

Melting point:

95 °C (dec.) (lit.)

Boiling point:

274.8±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

pka

7.29±0.58(Predicted)

form 

Crystalline Powder

color 

White to light beige

BRN 

6594341

InChI

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

InChIKey

SZYXKFKWFYUOGZ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

121219-16-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26-36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

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

2,3-Difluorophenylboronic acid Usage And Synthesis

Chemical Properties

Off-white to light beige crystalline powder

Uses

suzuki reaction

Uses

2,3-Difluorophenylboronic acid is a useful reagent for the preparation of pharmaceutical and biologically active molecules.

Uses

Intermediates of Liquid Crystals

Synthesis

The general procedure for the synthesis of 2,3-difluorophenylboronic acid from tri-n-propyl borate and 1,2-difluorobenzene is as follows: in a 1L three-necked flask equipped with a mechanical stirrer, nitrogen inlet and outlet, pressure-balancing dropping funnel, and a thermometer, 1,2-difluorobenzene (40 g, 0.35 mol) and anhydrous tetrahydrofuran (400 ml) were added. Nitrogen was introduced to displace the air in the reaction system and a weak flow of nitrogen was maintained throughout the reaction. The reaction mixture was cooled to -78 °C using a dry ice/acetone bath, followed by the slow dropwise addition of 2.5 mol/L hexane solution of n-butyllithium (140 ml, 0.35 mol) through a dropping funnel, controlling the reaction temperature to not exceed -70 °C. After the dropwise addition of n-butyllithium solution was completed, the reaction mixture was continued to be stirred at -78 °C for 2 hours. Subsequently, tri-n-propyl borate (66 g, 0.35 mol) was added dropwise, again keeping the reaction temperature below -70 °C. After the addition of tri-n-propyl borate, the cooling bath was withdrawn and the reaction mixture was allowed to warm up naturally to room temperature with continuous stirring. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give a viscous liquid residue. The residue was acidified and the resulting propanol was subsequently evaporated. The precipitated solid product was collected by filtration, washed with hexane and purified by aqueous recrystallization to give a final white crystalline 2,3-difluorophenylboronic acid 47 g in 85% of theoretical yield.

References

[1] Patent: US2013/20532, 2013, A1. Location in patent: Paragraph 0042
[2] Journal of Materials Chemistry C, 2014, vol. 2, # 5, p. 891 - 900

2,3-Difluorophenylboronic acid(121219-16-7)Related Product Information

• 2,4-Difluorobenzoic acid
• 1,3-Difluorobenzene
• Ethyl 2-(Chlorosulfonyl)acetate
• Folic acid
• 4-Fluorobenzeneboronic acid
• Phenylboronic acid
• 1,2-Difluorobenzene
• Citric acid
• Ascoric Acid
• 2,3,6-Trifluorophenylboronic acid
• 2,3,4-Trifluorophenylboronic acid
• 2,3-Difluoro-6-methoxyphenylboronic acid
• 2 3-DIFLUORO-4-FORMYPHENYLBORONIC ACID
• 2,3,4,5,6-PENTAFLUOROBENZENEBORONIC ACID
• 2,4-Dinitrofluorobenzene
• 2,3,4,5-TETRAFLUOROBENZENEBORONIC ACID
• 2,3,4,6-TETRAFLUOROBENZENEBORONIC ACID
• 2,3,5-Trifluorophenylboronic acid