TCI
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Description
2,5-Dibromo-3-fluorothiophene is a fluorinated building block based on a thiophene ring, carrying two bromine atoms at the 2- and 5-positions and a single fluorine atom at the 3-position. This substitution pattern makes it a highly useful starting material in the synthesis of conjugated compounds, because the two bromo groups act as reactive connection points for transition-metal-catalysed cross-coupling reactions. In laboratory practice, the compound is frequently used to construct thiophene oligomers and polymers, to assemble acceptor–donor units, and to prepare fluorinated heterocyclic derivatives that are difficult to obtain through direct synthetic routes.
The advantage that leads researchers to select this material lies in the role of the fluorine atom. Fluorine is strongly electronegative yet small in size, so it can lower the energy levels of the molecular orbitals without introducing significant steric disturbance to chain packing density. In materials research practice, this is often associated with improved stability towards oxidation and more ordered chain arrangement. At the same time, the two bromine atoms at the terminal positions of the ring provide good and well-directed reactivity in Suzuki, Stille, and Kumada couplings, allowing chain extension to be carried out in a controlled manner.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on organic electronic materials, conjugated polymers, and fluorinated heterocyclic chemistry. It is normally handled at small synthetic scale on the bench or in a fume hood, as part of multi-step routes where the dibrominated core is elaborated stepwise. Supplied under the TCI brand, it fits research settings that require a defined, reproducible fluorinated intermediate rather than one prepared in-house.
Laboratory Applications
- Cross-coupling synthesis: the two terminal bromine atoms serve as reactive handles for transition-metal-catalysed Suzuki, Stille, and Kumada reactions, giving directed and controllable bond formation.
- Thiophene oligomer construction: the difunctional 2,5-substitution pattern allows stepwise chain extension, so researchers can build defined oligomeric sequences from a single reliable core unit.
- Conjugated polymer preparation: symmetrical dibromination at both ring termini supports polymerisation routes in which the fluorinated thiophene is incorporated repeatedly along the backbone.
- Acceptor–donor unit assembly: the electron-withdrawing fluorine substituent lowers molecular orbital energy levels, making this unit useful when assembling acceptor–donor architectures for organic electronic materials.
- Fluorinated heterocycle derivatisation: the compound gives access to fluorinated heterocyclic derivatives that are difficult to obtain by direct synthetic routes starting from unsubstituted thiophenes.
Specifications
- Brand: TCI
- Product code: D5729
- CAS number: 32431-85-9
- Chemical name: 2,5-Dibromo-3-fluorothiophene
- Category: Chemistry > Building Blocks > Fluorinated Building Blocks
- Pack sizes: available in standard research quantities as offered by TCI; please confirm the required pack size when ordering
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated place, away from direct sunlight, heat sources, and incompatible materials, and follow the storage conditions stated on the manufacturer's label and safety data sheet. Keep the material in its original supplier container or in a chemically compatible, clearly labelled vessel, and reseal it promptly after each use to limit exposure to moisture and air. All handling should take place in a fume hood by trained personnel wearing appropriate personal protective equipment, including safety glasses, gloves, and a laboratory coat. Consult the safety data sheet before use, and dispose of residues and contaminated materials in accordance with applicable laboratory waste procedures.
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