4''-PROPYL-3-FLUOROBIPHENYL-4-BORONIC ACID Chemical Properties

Boiling point:

412.5±55.0 °C(Predicted)

Density 

1.17±0.1 g/cm3(Predicted)

vapor pressure 

0-0.004Pa at 20-50℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

8.41±0.58(Predicted)

form 

Solid

color 

White to Light yellow

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C15H16BFO2/c1-2-3-11-4-6-12(7-5-11)13-8-9-14(16(18)19)15(17)10-13/h4-10,18-19H,2-3H2,1H3

InChIKey

XZGCBSYWWZAXRC-UHFFFAOYSA-N

SMILES

B(C1=CC=C(C2=CC=C(CCC)C=C2)C=C1F)(O)O

LogP

4.9 at 25℃ and pH6.4

Safety Information

HS Code 

2931900090

4''-PROPYL-3-FLUOROBIPHENYL-4-BORONIC ACID Usage And Synthesis

Chemical Properties

White powder

Uses

4''-Propyl-3-fluoro-biphenyl-4-boronic acid

Synthesis

The general procedure for the synthesis of (3-fluoro-4'-propyl-[1,1'-biphenyl]-4-yl)boronic acid from triisopropyl borate and 3-fluoro-4-propylbiphenyl was as follows: 3-fluoro-4-propylbiphenyl (22.2 g, 0.104 mol) and 150 mL of tetrahydrofuran were added to a reaction vessel equipped with a dropping funnel. The mixture was heated to 70 °C, followed by the slow dropwise addition of 124 mL of sec-butyllithium solution (1.0 mol/L). The reaction mixture was stirred at 70 °C for 2 h. Triisopropyl borate (25.3 g, 0.135 mol) was added dropwise. After continued stirring for 2 hours, the reaction mixture was cooled to 0 °C and 300 mL of 10% hydrochloric acid solution was added slowly and dropwise. After stirring for 1 h at room temperature, aqueous washing was performed to remove the salts. Eventually, by concentration and drying treatment, (3-fluoro-4'-propyl-[1,1'-biphenyl]-4-yl)boronic acid (25.7 g, 0.0995 mol) was obtained.

References

[1] Patent: JP2015/110531, 2015, A. Location in patent: Paragraph 0108; 0110

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