3-Bromo-9H-carbazole
- CAS No.
- 1592-95-6
- Chemical Name:
- 3-Bromo-9H-carbazole
- Synonyms
- 2-bromo-9H-carbazole;3-BROMOCARBAZOLE;9H-Carbazole, 3-bromo-;3-broMidecarbazole;Carbazole, 3-bromo-;3- broMinecarbazole;3-Bromo-9H-carbazoL;3-Bromocarbazole >3-BROMO-9H-CARBAZOLE;3-BroMocarbazole (3BC)
- CBNumber:
- CB2444848
- Molecular Formula:
- C12H8BrN
- Molecular Weight:
- 246.1
- MDL Number:
- MFCD00222621
- MOL File:
- 1592-95-6.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| 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) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302-H315-H319-H335 | |||||||||
| Precautionary statements | P261-P264-P270-P301+P312-P302+P352-P305+P351+P338 | |||||||||
| target organs | Respiratory system | |||||||||
| 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 | |||||||||
| Storage Class | 11 - Combustible Solids | |||||||||
| Hazard Classifications | Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
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| NFPA 704 |
|
3-Bromo-9H-carbazole price More Price(98)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 777153 | 3-Bromocarbazole 97% (GC) | 1592-95-6 | 1g | $64.6 | 2023-06-20 | Buy |
| TCI Chemical | B3458 | 3-Bromocarbazole >97.0%(GC) | 1592-95-6 | 5g | $59 | 2026-04-30 | Buy |
| TCI Chemical | B3458 | 3-Bromocarbazole >97.0%(GC) | 1592-95-6 | 25g | $206 | 2026-04-30 | Buy |
| Usbiological | 263687 | 3-Bromocarbazole Asreported | 1592-95-6 | 50g | $722 | 2026-06-03 | Buy |
| Usbiological | 263687 | 3-Bromocarbazole Asreported | 1592-95-6 | 100g | $842 | 2026-06-03 | Buy |
3-Bromo-9H-carbazole Chemical Properties, Uses, Production
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.
Synthesis
86-74-8
1592-95-6
General procedure for the synthesis of 3-bromocarbazole from carbazole: Carbazole (10 g, 59.80 mmol) was added to N,N-dimethylformamide (DMF, 67 mL) and stirred at room temperature for 15 min. A solution of N-bromosuccinimide (NBS, 10.6 g, 59.56 mmol) in DMF (100 mL) was slowly added dropwise at 0 °C. After the dropwise addition was completed, the reaction mixture was gradually warmed up to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, the mixture was poured into water and a white precipitate precipitated. The precipitate was collected by filtration and dissolved in dichloromethane. The organic layer was washed with water to remove water soluble impurities. The organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The resulting white solid was purified by ethanol recrystallization to give 3-bromocarbazole in colorless crystalline form (10.65 g, 72% yield). The structure of the product was confirmed by 1H-NMR (CDCl3, 400 MHz) and mass spectrometry (ESI): 1H-NMR δ 8.34 (bs, 1H), 8.15 (d, J = 7.8 Hz, 1H), 7.48 (d, J = 8.2 Hz, 1H), 7.45 (m, 1H), 11.42 (s, 1H); MS (ESI) m/z 246 ( M+).
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 Preparation Products And Raw materials
Raw materials
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Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Shanghai Future Optoetech Co. Ltd | 19299290913 | sales@futureoled.com | China | 20 | 58 |
| Zhengzhou HQ Material Co., Ltd. | 86-0371-67759225 13526468238 | 3165471285@qq.com | China | 812 | 55 |
| Sunshine Optoelectronic | 027-027-87915283 15972929998 | sales@sunshine-oled.com | China | 683 | 58 |
| Zhengzhou Shengyi New Material Technology Co., LTD | 0371-63891666 18037898020 | sales@sinoemat.com | China | 38 | 58 |
| Pingdingshan Longwei Biotechnology Co. , Ltd. | 15343756688 | 3079249712@qq.com | China | 300 | 58 |
| Puyang Huicheng Electronic Material Co. Ltd. | 0393-0393-8910800 15039333257 | info@huichengchem.com | China | 588 | 64 |
| NINGBO INNO PHARMCHEM CO.,LTD. | 15558396803 | sales@nbinno.com | China | 135 | 58 |
| Creasyn Finechem(Tianjin) Co., Ltd. | 022-83946278 13820372920 | sales@creasyn.com | China | 968 | 68 |
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| Meryer (Shanghai) Chemical Technology Co., Ltd. | 4006356688 18621169109 | market03@meryer.com | China | 40202 | 62 |
View Latest Price from 3-Bromo-9H-carbazole manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-06-30 | 3-Bromo-9H-carbazole
1592-95-6
|
1KG | 99.0% | 10000KGS | Shaanxi Dideu New Materials Co. Ltd | ||
 |
2026-03-20 | 3-Bromo-9H-carbazole
1592-95-6
|
$10.00 | 1KG | 99% | 5tons | Hebei Chuanghai Biotechnology Co., Ltd | |
 |
2026-02-02 | 3-Bromo-9H-carbazole
1592-95-6
|
1g | 99% | 2000tons | Shaanxi Dideu Medichem Co. Ltd |
-
- 3-Bromo-9H-carbazole
1592-95-6
- 99.0%
- Shaanxi Dideu New Materials Co. Ltd
-
- 3-Bromo-9H-carbazole
1592-95-6
- $10.00
- 99%
- Hebei Chuanghai Biotechnology Co., Ltd
-
- 3-Bromo-9H-carbazole
1592-95-6
- 99%
- Shaanxi Dideu Medichem Co. Ltd
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