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3,6-Dibromocarbazole
1. Basic Information
Name: 3,6-Dibromocarbazole
Alias: 3,6-Dibromo-9H-carbazole
CAS No.: 6825-20-3
Molecular Formula: C12H7Br2N
Molecular Weight: 321.00
Category: Optoelectronic material intermediate, OLED monomer raw material, organic semiconductor building block, pharmaceutical heterocyclic reagent
2. Physical and Chemical Properties
Physical Properties
- Appearance: Off-white to light beige crystalline powder
- Odor: Odorless with faint characteristic aromatic heterocycle smell
- Solubility: Soluble in hot toluene, chloroform, THF, DMF and DMSO; slightly soluble in cold ethanol; insoluble in water, petroleum ether and aliphatic alkanes
- Melting Point: 214–218 °C
- Predicted Density: 1.86 g/cm3
- Hygroscopy: Non-hygroscopic under normal sealed storage environment
- Aqueous property: Weakly alkaline nitrogen heterocycle; stable in neutral cold water without spontaneous hydrolysis at room temperature
Chemical Properties
- Molecular structure: Carbazole parent ring with two bromine atoms substituted at C3 and C6 positions; contains reactive N-H bond and two aryl bromide sites suitable for cross-coupling reactions
- Cross-coupling reactivity: Aryl bromide groups undergo Suzuki, Buchwald, Sonogashira and Stille coupling to construct conjugated organic luminescent skeletons
- N-H functionalization: The pyrrolic NH on carbazole can be alkylated, arylated or protected to modify molecular solubility and optoelectronic performance
- Photostability: Moderately light-sensitive; long-term intense UV irradiation leads to slight discoloration and trace de-bromination impurities
- Thermal stability: Stable below 200 °C; heating above melting point triggers thermal decomposition and releases irritant bromine-containing volatile substances
- Compatibility: Compatible with anhydrous high-boiling aromatic and polar aprotic solvents; incompatible with strong oxidants and concentrated strong alkali under heating
3. Main Application Fields
1. OLED & Organic Optoelectronic Intermediate (Core Application)
Key monomer for synthesizing hole transport materials, fluorescent emitters and thermally activated delayed fluorescence (TADF) materials for organic light-emitting diodes
2. Organic Semiconductor Raw Material
Precursor for conjugated polymer semiconductors applied in organic field-effect transistors (OFET) and organic solar cells
3. Pharmaceutical Synthetic Building Block
Substrate for preparing carbazole-based anti-tumor, anti-viral and neuroprotective small-molecule APIs via coupling derivatization
4. Laboratory Organic Synthesis Reagent
Standard dibromocarbazole model compound for conjugated molecule design and cross-coupling reaction research
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 6825-20-3 |
| Molecular Formula | C12H7Br2N |
| Appearance | Uniform pale off-white crystalline powder without dark discoloration |
| HPLC Purity | Optoelectronic Grade ≥99.5%, Synthetic Grade ≥99.0% |
| Melting Point | 214–218 °C |
| Water Content (KF) | ≤0.20% |
| Residue on Ignition | ≤0.05% |
| Mono-Bromo 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 fiber drum |
| Storage Condition | Hermetically sealed cool dry warehouse below 25 °C, full light shielding, isolated from strong oxidants and alkaline materials |
| Transportation Requirement | Light-sensitive brominated carbazole crystalline powder, moisture-proof sealed packaging, separated from corrosive hazardous goods |
| Shelf Life | 24 months under nitrogen vacuum sealed storage |
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