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Description
TCI D4304 is 2,5-Dibromo-3-methylthiophene, a thiophene derivative carrying bromine atoms at both alpha positions of the ring together with a methyl group at the 3-position. As a heterocyclic building block, this compound is an essential starting material for constructing polythiophene chains and a wide range of conjugated materials. The two bromine atoms sit on reactive positions, making the compound a ready-to-use electrophilic partner in various transition-metal-catalysed cross-coupling reactions, while the methyl group contributes a mild electron-donating character and helps tune solubility.
Its practical value comes from the symmetrical difunctional pattern at the 2- and 5-positions, precisely the points required to extend conjugation along a thiophene chain. The carbon–bromine bonds on the thiophene ring are sufficiently reactive towards Suzuki, Stille, and Kumada couplings as well as Grignard metathesis type polymerisation, so researchers can select the method that best matches the equipment and catalysts available to them. The methyl group at the 3-position also renders the two alpha positions electronically and sterically inequivalent, a property exploited to control regiochemistry and produce polymers with more ordered side-chain arrangements.
In Indonesian laboratories, this material is typically found in university and institutional research groups working on organic electronics, conjugated polymers, and synthetic heterocyclic chemistry. It is generally used at bench scale for the preparation of monomers and oligomers, for method development in cross-coupling chemistry, and for reference syntheses supporting graduate and postgraduate research programmes, where a well-defined dibrominated thiophene building block shortens the route to more elaborate conjugated targets.
Laboratory Applications
- Polythiophene synthesis — the symmetrical 2,5-dibromo pattern provides two reactive coupling points that allow chain extension along the thiophene backbone in a controlled, repeatable manner.
- Suzuki cross-coupling — the carbon–bromine bonds react readily with boronic acid partners, letting researchers assemble biaryl and extended conjugated frameworks using widely available palladium catalyst systems.
- Stille and Kumada coupling — both alpha bromines serve as reliable electrophilic partners with organostannane or Grignard reagents, offering an alternative route when boron chemistry is unsuitable.
- Grignard metathesis polymerisation — the dibrominated thiophene core is well suited to GRIM-type chain-growth polymerisation, giving access to conjugated polymers for organic electronics research.
- Regiochemistry studies — the 3-methyl group makes the two alpha positions electronically and sterically inequivalent, which researchers exploit to direct selectivity and obtain more ordered side-chain arrangements.
Specifications
- Brand: TCI
- CAS number: 13191-36-1
- Chemical name: 2,5-Dibromo-3-methylthiophene
- Category: Chemistry > Building Blocks > Heterocyclic Building Blocks
- Pack sizes: available in standard TCI catalogue pack sizes; please confirm the required size when ordering
- Storage: keep in the original tightly closed container, away from light and heat, following the manufacturer's stated storage conditions on the label and safety data sheet
Handling and Storage
Store the material in its original tightly closed container in a cool, dry, well-ventilated area, protected from light, heat, and ignition sources, and follow the storage conditions stated by the manufacturer on the product label and safety data sheet. Amber glass or the supplied original packaging is preferred, and containers should be resealed promptly after use to limit exposure to air and moisture. Handle in a fume hood using safety goggles, chemical-resistant gloves, and a laboratory coat, and avoid contact with skin, eyes, and clothing as well as inhalation of vapours. Keep away from incompatible materials such as strong oxidising agents, and dispose of residues and contaminated materials in accordance with institutional chemical waste procedures and applicable local regulations. Consult the safety data sheet before first use.
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