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2-Bromocarbazole
1. Basic Information
Name: 2-Bromocarbazole
Alias: 2-Bromo-9H-carbazole
CAS No.: 3652-90-2
Molecular Formula: C12H8BrN
Molecular Weight: 246.10
Category: OLED optoelectronic intermediate, cross-coupling reaction substrate, organic semiconductor monomer, pharmaceutical carbazole building block
2. Physical and Chemical Properties
Physical Properties
- Appearance: Off-white to pale beige crystalline powder
- Odor: Odorless aromatic heterocycle smell
- Solubility: Soluble in hot THF, DMF, DMSO, toluene, chloroform; slightly soluble in hot ethanol; insoluble in cold water, petroleum ether
- Melting Point: 224–228 °C
- Predicted Density: 1.56 g/cm3
- Hygroscopy: Non-hygroscopic under sealed normal storage
- Aqueous property: Weakly alkaline nitrogen-containing aromatic heterocycle, stable in neutral cold water
Chemical Properties
- Molecular structure: Carbazole parent ring with single bromine substitution at C2 position, contains reactive N-H pyrrole group and aryl bromide active site
- Cross-coupling reactivity: Aryl bromide undergoes Suzuki, Buchwald, Sonogashira, Stille coupling to synthesize hole transport materials, TADF luminescent materials
- N-H modification: Nitrogen hydrogen can be alkylated, arylated to adjust molecular solubility and photoelectric performance
- Photostability: Slightly light-sensitive; long-time UV irradiation causes minor de-bromination and discoloration
- Thermal stability: Stable below 210 °C; above melting point heating decomposes to release irritant bromine-containing volatile fumes
- Compatibility: Compatible with high-boiling aromatic and polar aprotic solvents; incompatible with strong oxidants and concentrated strong alkali under heating
3. Main Application Fields
1. Organic Optoelectronic Material Intermediate (Core Application)
Key monomer for OLED hole transport layers, fluorescent emitters, delayed fluorescence luminescent materials; raw material for organic field-effect transistor semiconductors
2. Pharmaceutical Synthetic Building Block
Precursor for carbazole-based anti-tumor, anti-viral, neuroprotective small molecule drugs via coupling derivatization
3. Laboratory Cross-Coupling Standard Substrate
Model bromocarbazole compound for organic synthesis research on conjugated molecule construction
4. Organic Dye Precursor
Raw material for high light fastness carbazole functional dyes and photosensitizers
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 3652-90-2 |
| Molecular Formula | C12H8BrN |
| Appearance | Uniform pale off-white crystal without dark impurities |
| HPLC Purity | OLED Optoelectronic Grade ≥99.5%, Synthetic Grade ≥99.0% |
| Melting Point | 224–228 °C |
| Water Content (KF) | ≤0.20% |
| Dibromocarbazole Impurity | ≤0.10% |
| Single Unknown Impurity | ≤0.10% |
| Heavy Metals (Pb) | ≤5 ppm |
| Packaging | Light-proof nitrogen-filled aluminum foil vacuum bag; bulk 25kg PE lined sealed fiber drum |
| Storage Condition | Hermetically sealed cool dry warehouse below 25 °C, light shielding, isolated from oxidants and alkaline substances |
| Transportation Requirement | Stable brominated aromatic crystal powder, general chemical transport standard, avoid damp stacking |
| Shelf Life | 24 months under intact nitrogen sealed packaging |
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