1-Chloro-9H-carbazole Chemical Properties

Melting point:

125 °C

Boiling point:

388.7±15.0 °C(Predicted)

Density 

1.363±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

16.16±0.30(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C12H8ClN/c13-10-6-3-5-9-8-4-1-2-7-11(8)14-12(9)10/h1-7,14H

InChIKey

DBDCPKPHHCECLZ-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC=C2)C2=C1C(Cl)=CC=C2

1-Chloro-9H-carbazole Usage And Synthesis

Uses

1-Chloro-9H-carbazole is an important organic synthetic raw material and OLED intermediate compound for organic molecules used in optoelectronic devices.

Synthesis

General procedure for the synthesis of 1-chloro-9H-carbazole and 3-chloro-9H-carbazole from carbazole: Carbazole (0.2 mmol), N-chlorosuccinimide (NCS, 0.26 mmol), camphorsulfonate (D-CSA, 0.1 mmol), and 1,3-bis(1-adamantyl)imidazolium tetrafluoroborate (0.01 mmol) were prepared in a 1,4-dioxane ( 1 mL) was stirred well. The reaction was carried out at room temperature (25 °C) for 24 h under air atmosphere. The reaction progress was monitored by gas chromatography-mass spectrometry (GC-MS). When the carbazole was completely consumed, the reaction was quenched with saturated aqueous sodium bicarbonate (NaHCO3) solution (4 mL). The reaction mixture was extracted with ethyl acetate (EtOAc, 4 mL × 3). The organic layer was washed with pure water (4 mL × 3). The organic layers were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to remove the solvent to give the crude product. Finally, the crude product was purified by silica gel fast column chromatography.

References

[1] Synlett, 2015, vol. 26, # 20, p. 2831 - 2834
[2] Journal of the Chemical Society. Perkin Transactions 2, 2000, # 7, p. 1583 - 1595