(4-(9-phenyl-9H-carbazol-3-yl)phenyl)boronic acid Chemical Properties

Boiling point:

555.9±60.0 °C(Predicted)

Density 

1.18±0.1 g/cm3(Predicted)

storage temp. 

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

pka

8.62±0.17(Predicted)

Appearance

White to off-white Solid

(4-(9-phenyl-9H-carbazol-3-yl)phenyl)boronic acid Usage And Synthesis

Synthesis

Example 2: In this Example, an example of the preparation of 3-[4-(9-phenanthrenyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn) represented by structural formula (102) is described. Step 1: Synthesis of 4-(9-phenyl-9H-carbazol-3-yl)phenylboronic acid To a 300 mL three-neck flask was added 8.0 g (20 mmol) of 3-(4-bromophenyl)-9-phenyl-9H-carbazole and the atmosphere in the flask was replaced with nitrogen. Subsequently, 100 mL of dehydrated tetrahydrofuran (THF) was added to the flask and the mixture was cooled to -78°C. 3.4 mL (30 mmol) of trimethyl borate was slowly added to the mixture. After the addition was completed, the reaction mixture was stirred at -78°C for 2 hr and then continued to stir for 18 hr at room temperature. Upon completion of the reaction, 1 M dilute hydrochloric acid was added dropwise to the reaction solution until the solution became acidic and stirring was continued for 7 hours. The reaction mixture was extracted with ethyl acetate and the organic layer was washed with saturated brine. After washing, anhydrous magnesium sulfate was added to the organic layer to remove water. After filtration to remove the magnesium sulfate, the filtrate was concentrated and hexane was added to the concentrate. Crystallization was promoted by ultrasonic treatment followed by recrystallization to give 6.4 g of the target product in white powder form in 88% yield. The reaction scheme for step 1 is shown in (F2-1).

References

[1] Patent: US2012/77987, 2012, A1. Location in patent: Page/Page column 43-44
[2] Patent: WO2013/15144, 2013, A1. Location in patent: Paragraph 0357-0360