9-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole Chemical Properties

Melting point:

162.0 to 166.0 °C

Boiling point:

478.3±27.0 °C(Predicted)

Density 

1.11

storage temp. 

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

solubility 

soluble in Toluene

form 

powder to crystal

color 

White to Almost white

Safety Information

HS Code 

2933998090

9-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole Usage And Synthesis

Application

9-Phenylacetic acid ester is an ester organic compound that can be used as a pharmaceutical intermediate.

Chemical Properties

Pale yellow powder

Synthesis

The general procedure for the synthesis of 9-phenyl-9H-carbazole-3-boronic acid pinacol ester from 3-bromo-N-phenylcarbazole and bis(pinacolato)diboron (1.2 eq.), potassium acetate (1.5 eq.), and PdCl2 (dppf) (0.02 eq.) was carried out by dissolving halogenated arylenes (1.0 eq.), bis(pinacolato)diboron (1.2 eq.), potassium acetate (1.5 eq.) and PdCl2 (dppf) (0.02 eq.), protected by nitrogen, in anhydrous 1,4- dioxane (20 mL) and the reaction was refluxed overnight. After completion of the reaction, the reaction was cooled to room temperature, the reaction mixture was poured into water and extracted with dichloromethane. The organic layers were combined, washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure and the crude product was purified by silica gel column chromatography, eluting with a solvent mixture of dichloromethane and hexane to give the pure product 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (3). Specific example: compound 3 (4.1 g, 88.4% yield) was obtained using 3-bromo-9-phenyl-9H-carbazole (4 g, 12.4 mmol), bis(pinacolato)diboron (3.79 g, 14.9 mmol), potassium acetate (1.9 g, 18.6 mmol) and PdCl2 (dppf) (0.14 g, 0.02 mmol) , a white solid with a melting point of 160°C.

References

[1] Organic Electronics: physics, materials, applications, 2014, vol. 15, # 7, p. 1413 - 1421
[2] Patent: KR2015/98062, 2015, A. Location in patent: Paragraph 0135-0139; 0151; 0152
[3] Patent: KR2015/103948, 2015, A. Location in patent: Paragraph 0323-0326
[4] Patent: KR101531614, 2015, B1. Location in patent: Paragraph 0842-0845
[5] Patent: KR101486562, 2015, B1. Location in patent: Paragraph 0849-0853

9-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole(1126522-69-7)Related Product Information

• 9-(Biphenyl-3-yl)-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole
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• 9-Phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole
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• (9-phenyl-9H-carbazol-2-yl)boronic acid
• 9- Phenyl-2-(4,4,5,5-tetraMethyl- 1,3,2-dioxaborolan-2-yl)-9H-carbazole