(4'-Pentyl[1,1'-biphenyl]-4-yl)-boronic acid Chemical Properties

Boiling point:

436.4±48.0 °C(Predicted)

Density 

1.08±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

soluble in Methanol

form 

powder to crystal

pka

8.61±0.17(Predicted)

color 

White to Almost white

Safety Information

HS Code 

2931900090

(4'-Pentyl[1,1'-biphenyl]-4-yl)-boronic acid Usage And Synthesis

Chemical Properties

off-white powder

Synthesis

General procedure for the synthesis of 4-pentylbiphenylboronic acid from 4'-bromo-4-pentylbiphenyl: 4'-bromo-4-pentylbiphenyl (3 g, 9.9 mmol) was added in a single addition to magnesium shavings (0.27 g, 11.1 mmol) in an iodine-catalyzed reaction using tetrahydrofuran (40 mL) as solvent. The reaction mixture was heated at reflux for 3 h and subsequently cooled to -78 °C and trimethyl borate (2.06 g, 19.8 mmol) was added slowly and dropwise. The reaction system was gradually warmed to room temperature over 1 h, then acidified with 2 M hydrochloric acid (50 mL) and extracted with ether (3 x 50 mL). The combined ether extracts were back-extracted with 1 M sodium hydroxide solution (100 mL). The aqueous phase was acidified with concentrated hydrochloric acid and extracted again with ether (3×50 mL), the organic phase was dried with anhydrous magnesium sulfate, and the solvent was removed by concentration under reduced pressure to obtain 4-pentylbiphenylboronic acid (2.07 g, 78% yield), the product was an off-white powder.

References

[1] Patent: EP2098520, 2009, A1. Location in patent: Page/Page column 18
[2] Tetrahedron Letters, 2014, vol. 55, # 9, p. 1631 - 1634