| Identification | Back Directory | [Name]
3-Bromo-9H-carbazole | [CAS]
1592-95-6 | [Synonyms]
3-BROMOCARBAZOLE
3-broMidecarbazole
3- broMinecarbazole
Carbazole, 3-bromo-
3-Bromo-9H-carbazoL
3-Bromocarbazole >
3-BROMO-9H-CARBAZOLE
2-bromo-9H-carbazole
9H-Carbazole, 3-bromo-
3-BroMocarbazole
(3BC)
3-Bromocarbazole 97% (GC)
3-BroMo-9H-carbazole, 95+% | [EINECS(EC#)]
679-545-7 | [Molecular Formula]
C12H8BrN | [MDL Number]
MFCD00222621 | [MOL File]
1592-95-6.mol | [Molecular Weight]
246.1 |
| Chemical Properties | Back Directory | [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 | [form ]
Solid | [pka]
16.43±0.30(Predicted) | [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]
9H-Carbazole, 3-bromo-(1592-95-6) |
| Hazard Information | Back Directory | [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]
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.
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