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4-Bromo-9H-carbazole
1. Basic Information
Name: 4-Bromo-9H-carbazole
CAS No.: 3652-89-9
Molecular Formula: C12H8BrN
Molecular Weight: 246.10
Category: Brominated carbazole aromatic heterocyclic optoelectronic intermediate
2. Physical and Chemical Properties
Physical Properties
- Appearance: Off-white to light pale yellow crystalline powder
- Odor: Faint characteristic heterocyclic odor
- Solubility: Soluble in THF, chloroform, toluene, dichloromethane; slightly soluble in hot methanol and ethanol; insoluble in water and aliphatic alkanes
- Melting Range: 126–130 °C
- Hygroscopy: Non-hygroscopic under normal ambient humidity
- Aqueous Property: Lipophilic neutral nitrogen-containing heterocycle, no dissolution in water
Chemical Properties
- Molecular Structure: Carbazole fused ring with bromine substitution at the 4-position, contains active N-H group on the five-membered nitrogen ring
- N-H Activity: The hydrogen atom on nitrogen can undergo alkylation, acylation and deprotonation reactions
- Aryl Bromide Reactivity: C-Br bond supports Suzuki, Buchwald, Sonogashira cross-coupling reactions for conjugated material synthesis
- Thermal Stability: Stable below 100 °C; slight oxidative discoloration after long-time heating above melting point
- Photostability: Sensitive to ultraviolet light; prolonged light exposure generates trace oxidation impurities and darkens the solid
- Compatibility: Compatible with most aprotic polar organic solvents; incompatible with strong oxidants, concentrated strong alkali and heavy metal salts
3. Main Application Fields
1. Organic Optoelectronic Material Intermediate (Core Application)
Key monomer for OLED hole transport materials, organic photoconductors, organic field-effect transistors and luminescent conjugated polymers; used to construct high-stability carbazole-based optoelectronic skeletons via palladium coupling reactions
2. Pharmaceutical Synthetic Intermediate
Building block for synthesizing antitumor, anti-inflammatory and central nervous system heterocyclic APIs with carbazole parent structure
3. HPLC Reference Standard
Reference substance for quantitative detection of bromocarbazole intermediates in optoelectronic chemical production
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 3652-89-9 |
| Molecular Formula | C12H8BrN |
| Appearance | Off-white crystalline powder without visible foreign particles |
| HPLC Purity | Optoelectronic Grade ≥99.5%; Synthetic Intermediate Grade ≥99.0% |
| Water Content (KF) | ≤0.30% |
| Melting Range | 126–130 °C |
| Residue on Ignition | ≤0.10% |
| Single Unknown Impurity | ≤0.10% |
| Heavy Metals (Pb) | ≤10 ppm |
| Packaging | Nitrogen-purged amber vacuum aluminum foil bags / PE-lined fiber drums |
| Storage Condition | Hermetically sealed dark dry warehouse below 25 °C; strictly isolated from light, oxidants and alkaline reagents |
| Transportation Requirement | Light-sensitive brominated heterocyclic solid, fully sealed light-proof moisture-proof packaging |
| Shelf Life | 24 months under nitrogen-filled vacuum sealed storage |
Safety Warning
Irritant brominated aromatic heterocyclic powder. Dust causes severe irritation to eyes, respiratory tract and skin; long-term skin contact may induce allergic inflammation. All operations must be performed inside ventilated chemical fume hoods with dust respirators, chemical-resistant gloves and full-face safety goggles. Airtight dark storage is required to prevent photooxidation discoloration. Waste liquid needs organic solvent recovery and neutralization treatment; solid waste is classified as organic hazardous waste and must be disposed by licensed professional hazardous waste treatment facilities.
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