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3,3'-Dibromo-2,2'-bithiophene
1. Basic Information
Name: 3,3'-Dibromo-2,2'-bithiophene
Alias: 3,3'-Dibromo-2,2'-dithiophene
CAS No.: 51751-44-1
Molecular Formula: C8H4Br2S2
Molecular Weight: 324.05
Category: Brominated bithiophene organic semiconductor intermediate, conjugated polymer monomer, OLED/OPV optoelectronic raw material, cross-coupling reaction substrate
2. Physical and Chemical Properties
Physical Properties
- Appearance: Pale yellow crystalline powder
- Odor: Faint thiophene heterocyclic odor
- Solubility: Soluble in DCM, chloroform, THF, toluene, DMF; slightly soluble in hot ethanol; insoluble in water, hexane, petroleum ether
- Melting Point: 116–120 ℃
- Density (predicted): 1.92 g/cm3
- Hygroscopy: Non-hygroscopic under normal ambient humidity
- Aqueous property: Neutral aromatic heterocycle, stable in neutral water at room temperature
Chemical Properties
- Molecular structure: Two thiophene rings linked at 2,2'-position, bromine atoms substituted on 3 and 3' carbon; dual aryl bromide active sites for coupling polymerization
- Cross-coupling reactivity: Two C-Br bonds can carry out Suzuki, Stille, Negishi coupling reactions to construct long conjugated thiophene polymer chains
- Conjugated system characteristics: Planar bithiophene backbone with excellent electron transport performance, core unit for organic photoelectric materials
- Thermal stability: Stable below 110 ℃; prolonged heating above melting point causes partial debromination and carbonization
- Photostability: Light-sensitive; long-term UV irradiation breaks carbon-bromine bonds, darkens powder and produces impurities
- Compatibility: Compatible with anhydrous aprotic solvents; incompatible with strong reducing agents, concentrated strong alkali, strong oxidants
3. Main Application Fields
1. Organic Optoelectronic Material Monomer (Core Application)
Key monomer for synthesizing conjugated polythiophene derivatives; used in organic solar cells (OPV), organic light-emitting diodes (OLED), organic field-effect transistors (OFET)
2. Organic Synthesis Research Reagent
Dihalogenated conjugated substrate for developing new conjugated polymer synthesis processes
3. Organic Semiconductor & Conductive Material Precursor
Raw material for high-mobility organic conductive polymers, organic sensing film materials
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 51751-44-1 |
| Molecular Formula | C8H4Br2S2 |
| Appearance | Uniform pale yellow crystal without black impurities |
| HPLC Purity | Optoelectronic Grade ≥99.0% |
| Melting Point | 116–120 ℃ |
| Water Content (KF) | ≤0.10% |
| Residue on Ignition | ≤0.05% |
| Single Unknown Impurity | ≤0.10% |
| Heavy Metals (Pb) | ≤10 ppm |
| Packaging | Nitrogen-filled amber light-proof aluminum foil vacuum bag, 25kg PE lined light-shield fiber drum |
| Storage Condition | Hermetically sealed cool dry warehouse below 25 ℃, full light shielding, isolate reducing agents and oxidants |
| Transportation Requirement | Light-sensitive brominated thiophene crystal, sealed light-proof moisture-proof packaging, separated from food and corrosive chemicals |
| Shelf Life | 24 months under nitrogen vacuum sealed storage |
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