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Description
TCI D4181 is 4,4'-Dibromo-2,2'-bithiophene, a bithiophene derivative carrying bromine atoms at the 4 and 4' positions of the two thiophene rings. As a heterocyclic building block, this compound occupies an important place in the synthesis of conjugated materials because it supplies a ready-made bithiophene framework together with two reactive sites available for further elaboration. In the laboratory it serves as a monomer and as a synthetic intermediate for constructing oligothiophenes, substituted polythiophenes, and a wide range of small conjugated molecules studied in organic electronics and photochemistry.
The principal advantage of this compound lies in its beta-bromination pattern, at the 4 and 4' positions rather than the more common alpha positions. This arrangement leaves the 5 and 5' positions free, so that polymerization or chain extension can be directed toward the ring termini, while the beta bromine atoms act as handles for installing side groups through palladium-catalysed cross-coupling or through halogen–metal exchange. The carbon–bromine bonds on the thiophene rings are sufficiently reactive for Suzuki, Stille, Negishi, and Kumada reactions, which makes the compound a flexible platform for designing conjugated architectures with controlled substitution.
In Indonesian laboratories, materials of this type are typically used by university and institutional research groups working on organic semiconductors, conjugated polymers, and photoactive small molecules. It is normally handled in synthetic chemistry laboratories equipped for cross-coupling work, where it is weighed out in small quantities for multi-step preparations, purified intermediates, and structure–property studies. Because it functions as a starting material rather than a finished formulation, it is generally ordered in research-scale quantities to support ongoing method development and materials synthesis projects.
Laboratory Applications
- Conjugated polymer synthesis: the bithiophene core provides an extended conjugated unit while the free 5 and 5' positions allow chain growth to proceed along the polymer backbone.
- Palladium-catalysed cross-coupling chemistry: the reactive carbon–bromine bonds participate readily in Suzuki, Stille, Negishi, and Kumada couplings for attaching aryl or alkyl partners.
- Oligothiophene preparation: researchers use this building block to assemble defined thiophene sequences whose chain length and substitution pattern can be controlled step by step.
- Organic electronics materials research: the compound serves as a precursor for semiconducting small molecules and polymers investigated for their charge-transport and optical behaviour.
- Side-chain functionalisation via halogen–metal exchange: the beta bromine atoms can be converted into organometallic intermediates, giving access to substituents that tune solubility and packing.
Specifications
- Brand: TCI
- CAS number: 51285-60-0
- Chemical name: 4,4'-Dibromo-2,2'-bithiophene
- Category: Chemistry > Building Blocks > Heterocyclic Building Blocks
- Pack sizes: available in standard TCI research-scale packaging; please confirm the sizes currently listed for this catalogue number
- Storage note: keep in the tightly closed original container, protected from light and moisture
Handling and Storage
Store the container tightly closed in a cool, dry, and well-ventilated place, away from direct sunlight, heat sources, and incompatible chemicals. The original manufacturer packaging is the most suitable container; if the material is transferred, use a clean, dry, chemically resistant vessel with a secure closure and a clear label. Handle the compound in a fume hood, wearing safety goggles, a laboratory coat, and suitable chemical-resistant gloves. Avoid inhalation of dust and contact with skin or eyes, keep the container closed when not in use, and consult the manufacturer's safety data sheet before use and disposal.
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