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

Melting point:

147.0 to 151.0 °C

Boiling point:

478.3±27.0 °C(Predicted)

Density 

1.11±0.1 g/cm3(Predicted)

storage temp. 

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

form 

powder to crystal

color 

White to Almost white

Safety Information

HS Code 

2934.99.4400

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

Synthesis

2-Bromo-9-phenyl-9H-carbazole (8.3 g, 25.86 mmol) and pinacol ester of bisboronic acid (8.54 g, 33.61 mmol) were added to potassium acetate (5.08 g, 51.71 mmol) and Pd(dppf)Cl2 (0.42 g, 0.52 mmol) in 100 mL of 1,4-dioxane. The reaction mixture was refluxed and stirred for 12 hours. Upon completion of the reaction, the reaction mixture was extracted with dichloromethane and purified by silica gel column chromatography with an eluent ratio of hexane:dichloromethane=7:3 (v/v) to give 9.2 g of 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole in 94% yield. The product was analyzed by 1H NMR (1.31 (s, 12H), 7.23 (t, 1H), 7.36 (m, 2H), 7.49 (t, 1H), 7.58 (dd, 2H), 7.64 (t, 2H), 7.67 (d, 1H), 7.79 (s, 1H), 8.14 (dd, 2H)) and GC-MS (theoretical value: 369.19 g/ mol, measured value: 369 g/mol) characterization was confirmed.

References

[1] Patent: US2013/48975, 2013, A1. Location in patent: Paragraph 0058; 0059; 0060; 0061
[2] Patent: EP2930168, 2015, A1. Location in patent: Paragraph 0089; 0093; 0290
[3] Patent: KR2015/103948, 2015, A. Location in patent: Paragraph 0319-0322
[4] Patent: KR101550768, 2015, B1. Location in patent: Paragraph 0155 - 0158
[5] Patent: KR2015/98171, 2015, A. Location in patent: Paragraph 0138; 0142; 0155-0158

9- Phenyl-2-(4,4,5,5-tetraMethyl- 1,3,2-dioxaborolan-2-yl)-9H-carbazole(1246669-45-3)Related Product Information

• Carbazole
• 9-Phenyl-9H-carbazol-3-ylboronic acid
• (9-phenyl-9H-carbazol-2-yl)boronic acid
• 9-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole