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1-Chloro-9H-carbazole

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1-Chloro-9H-carbazole Basic information
Product Name:1-Chloro-9H-carbazole
Synonyms:1-chlorocarbazole;1-Chloro-9H-carbazole;9H-Carbazole, 1-chloro-
CAS:5599-70-2
MF:C12H8ClN
MW:201.65
EINECS:
Product Categories:
Mol File:5599-70-2.mol
1-Chloro-9H-carbazole Structure
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
pka16.16±0.30(Predicted)
AppearanceWhite to off-white Solid
InChIInChI=1S/C12H8ClN/c13-10-6-3-5-9-8-4-1-2-7-11(8)14-12(9)10/h1-7,14H
InChIKeyDBDCPKPHHCECLZ-UHFFFAOYSA-N
SMILESN1C2=C(C=CC=C2)C2=C1C(Cl)=CC=C2
Safety Information
MSDS Information
1-Chloro-9H-carbazole Usage And Synthesis
Uses1-Chloro-9H-carbazole is an important organic synthetic raw material and OLED intermediate compound for organic molecules used in optoelectronic devices.
Synthesis
Carbazole

86-74-8

1-Chloro-9H-carbazole

5599-70-2

3-chlorocarbazole

2732-25-4

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
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