3,6-Diphenyl-9H-carbazole Chemical Properties

Melting point:

186℃

Boiling point:

575℃

Density 

1.198

Flash point:

256℃

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

16.82±0.30(Predicted)

color 

White to Almost white

InChI

InChI=1S/C24H17N/c1-3-7-17(8-4-1)19-11-13-23-21(15-19)22-16-20(12-14-24(22)25-23)18-9-5-2-6-10-18/h1-16,25H

InChIKey

PCMKGEAHIZDRFL-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(C3=CC=CC=C3)C=C2)C2=C1C=CC(C1=CC=CC=C1)=C2

CAS DataBase Reference

56525-79-2

Safety Information

HS Code 

2933.99.8290

3,6-Diphenyl-9H-carbazole Usage And Synthesis

Uses

Used as an intermediate in organic synthesis and materials.

Description

3,6-Diphenyl-9H-carbazole, also known as 3,6-Diphenylcarbazole (DPhCz), is another electron-donating 9H-carbazole derivative that has an extended π-π conjugation from the carbazole fusion ring to the phenyl group attached to the 3,-6 position. The degree of electron donating strength is in the order of carbazole 3,6-dimethylcarbazole 3,6-diphenylcarbazole, resulting in the relatively red-shift of emissions of 3,6-dimethylcarbazole and 3,6-diphenylcarbazole while comparing non-substituted carbazoles.

Synthesis

Under nitrogen protection, 3,6-dibromocarbazole (5 g, 15.4 mmol), phenylboronic acid (4.1 g, 33.9 mmol), palladium triphenylphosphine (0.7 g, 0.6 mmol) and toluene (45 ml) were sequentially added to a dry reaction flask. Subsequently, 2M aqueous sodium carbonate solution (45 ml) was slowly added. The reaction mixture was stirred at 80°C for 8 hours. After completion of the reaction, the organic phase was separated and concentrated under reduced pressure using a rotary evaporator. Finally, the concentrated residue was purified by silica gel column chromatography to afford the target product 3,6-diphenylcarbazole (3.6 g, 74% yield).

References

[1] Patent: KR2015/6758, 2015, A. Location in patent: Paragraph 0362-0364
[2] Patent: EP2818468, 2014, A2. Location in patent: Paragraph 0102; 0103
[3] Patent: WO2010/46259, 2010, A1. Location in patent: Page/Page column 55
[4] Patent: TWI554499, 2016, B. Location in patent: Page/Page column 89
[5] Patent: TW2016/38086, 2016, A. Location in patent: Page/Page column 41; 42

3,6-Diphenyl-9H-carbazole(56525-79-2)Related Product Information

• 2,7-Dibromocarbazole
• 3,6-DI-2-PYRIDYL-1,2,4,5-TETRAZINE
• 2-HYDROXYCARBAZOLE
• 2-chloro-9H-carbazole
• 4-BroMo-9H-carbazole
• 3,6-Dibromocarbazole
• 2-BROMOCARBAZOLE
• 3-bromo-6-phenyl-9H-carbazole
• 3-phenyl-9H-carbazole
• 9H-Carbazole, 3,6-diiodo-
• 9-Phenyl-9H,9'H-[3,3']bicarbazolyl
• 3,6-BIS(TERT-BUTYL)CARBAZOLE
• 3-Bromo-9H-carbazole
• 3,6-Dibromo-9-phenyl-9H-carbazole
• 3,6-DIPHENYL-9H-CARBAZOLE
• 5-PHENYL-1H-INDOLE
• 3-METHYLCARBAZOLE