3-Bromo-9H-carbazole Chemical Properties

Melting point:

195 °C

Boiling point:

160℃/6mm

Density 

1.617±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

16.43±0.30(Predicted)

form 

Solid

color 

White

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C12H8BrN/c13-8-5-6-12-10(7-8)9-3-1-2-4-11(9)14-12/h1-7,14H

InChIKey

LTBWKAYPXIIVPC-UHFFFAOYSA-N

SMILES

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

EPA Substance Registry System

3-Bromocarbazole (1592-95-6)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-37/39-24/25

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29339900

3-Bromo-9H-carbazole Usage And Synthesis

Description

3-Bromo-9H-carbazole is an isomer to 2-Bromo-9H-carbazole, with the only difference being that 9H-carbazole is mono-brominated at 3-position. Blocked at 3-position, 3-Bromo-9H-carbazole derivatives reduce the chance of being oxidised to form excimers or oligomers. 3-bromo-9H-carbazole is a versatile building block that can be used to create a range of compounds, such as 9-Benzyl-3-bromo-9H-carbazole. 3-Bromo-9H-carbazole can be prepared by reacting 9H-carbzole with N-bromosuccinimide (NBS) In tetrahydrofuran at room temperature[1].

Chemical Properties

White to light yellow solid

Uses

3-Bromo-9H-carbazole is an aryl hydrocarbon receptor agonist. A standard for environmental testing and research. Substance for the bological potency study, characterization of mono to tetra-halogenated carbazoles.

Uses

3-Bromocarbazole is used as a intermediate for organic light-emitting diode(OLED) and pharmaceutical.

Preparation

3-Bromocarbazole synthesis: A solution of N-bromosuccinimide (1.1g, 5.98mmol) in dimethylformamide was added dropwise to a solution of carbazole (1, 1g, 5.96mmol) in dimethylformamide (15mL) at 0°C. The reaction mixture was then stirred at room temperature for 24h. The reaction was poured into distilled water to give a cream coloured precipitate. The precipitate was filtered off under vacuum and washed with distilled water (3 × 20mL). The precipitate was dissolved in ethyl acetate, dried with sodium sulfate and filtered. Upon concentration under reduced pressure the crude product was obtained as a brown solid. After crystallisation of the crude product with chloroform, the pure 3-Bromo-9H-carbazole(692 mg, 47%) was obtained as white crystals. Rf (ethyl acetate/hexane, 1:6 v/v): 0.43; melting point: 200–201°C.

References

[1] Peng-Mian Huang, Xiao-Chun Wang. “9-Benzyl-3-bromo-9H-carbazole.” Acta crystallographica. Section E, Structure reports online 65 Pt 8 (2009): o1763.

3-Bromo-9H-carbazole(1592-95-6)Related Product Information

• Carbazole
• POLY(N-VINYLCARBAZOLE)
• 3,6-Dibromo-9-ethylcarbazole
• 3,6-Dibromocarbazole
• Bromine
• 1-(3,6-DIBROMO-CARBAZOL-9-YL)-3-PYRROLIDIN-1-YL-PROPAN-2-OL
• TIMTEC-BB SBB006353
• 1-(3,6-DIBROMO-CARBAZOL-9-YL)-3-[4-(4-FLUORO-PHENYL)-PIPERAZIN-1-YL]-PROPAN-2-OL
• 1,4-Dimethyl-6-bromo-9H-carbazole
• 3,6-DIBROMO-9-VINYLCARBAZOLE
• 3,6-DIBROMO-9-(OXIRAN-2-YLMETHYL)-9H-CARBAZOLE
• 3,6-DIBROMO-ALPHA-(1-PIPERAZINYLMETHYL)-9H-CARBAZOLE-9-ETHANOL DIHYDROCHLORIDE
• 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL
• 3,6-Dibromo-9-phenyl-9H-carbazole
• 3-Bromo-9H-carbazole
• AKOS BC-1674
• 1-(4-[2-HYDROXY-3-(1,3,6-TRIBROMO-9H-CARBAZOL-9-YL)PROPYL]PIPERAZINO)-3-(1,3,6-TRIBROMO-9H-CARBAZOL-9-YL)PROPAN-2-OL DIHYDROCHLORIDE
• SALOR-INT L150053-1EA