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Description
TCI D4146 2,4-Dibromothiophene is a heterocyclic building block based on a thiophene ring carrying two bromine atoms at the 2- and 4-positions. Thiophene is one of the most widely used five-membered heterocycles in modern organic chemistry, appearing both in drug design and in the development of organic electronic materials. The presence of two bromine atoms turns this ring into a versatile platform for forming carbon–carbon and carbon–heteroatom bonds, allowing researchers to grow larger structures from a small, simple, and readily available core.
The property that makes this compound a frequent choice is its unsymmetrical bromine substitution pattern. The 2-position sits at the alpha position adjacent to the sulfur atom, while the 4-position sits at a beta position, and this difference in electronic environment means the two bromine atoms do not show equal reactivity in metal-catalysed coupling reactions or in halogen–metal exchange. That difference opens the way to selective stepwise functionalisation, something highly valuable when assembling conjugated molecules with a specific sequence of units. In addition, the thiophene ring contributes electron density that supports the electronic behaviour sought in the target structures.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on synthetic organic chemistry, medicinal chemistry, and organic electronic materials. It usually arrives as a catalogue item ordered in small research quantities for method development, thesis and dissertation work, and exploratory route scouting, where a reliable brominated heterocycle is needed as a starting point before scaling a synthetic sequence further.
Laboratory Applications
- Cross-coupling chemistry: the two bromine substituents serve as reactive handles for metal-catalysed carbon–carbon bond formation, letting researchers attach aryl or heteroaryl partners onto the thiophene core.
- Selective stepwise functionalisation: the differing reactivity of the alpha and beta bromines allows one position to be coupled first and the other later, giving controlled access to unsymmetrically substituted thiophenes.
- Conjugated material synthesis: the thiophene ring is a standard repeat unit in organic electronic materials, and this dibromide provides a defined entry point for building extended conjugated architectures.
- Medicinal chemistry scaffolds: thiophene is a common heterocycle in drug discovery, so this building block supports the preparation of analogue series around a small, synthetically flexible core.
- Halogen–metal exchange studies: the non-equivalent bromine environments make this compound useful for exploring regioselectivity in exchange reactions and for generating organometallic intermediates for further elaboration.
Specifications
- Brand: TCI
- CAS number: 3140-92-9
- Category: Chemistry > Building Blocks > Heterocyclic Building Blocks
- Product code: D4146
- Pack sizes: available in standard TCI research catalogue pack sizes; please confirm the pack size when ordering
- Storage: keep in the closed original container under the conditions indicated on the manufacturer's label
Handling and Storage
Store the material in its tightly closed original container in a cool, dry, and well-ventilated place, away from direct sunlight, heat sources, and incompatible chemicals, and follow the storage conditions stated on the manufacturer's label. Amber or otherwise light-protecting glass containers with chemically resistant closures are appropriate for any transferred portions, which should be clearly labelled with the product name and CAS number. Handle the compound in a fume hood using safety glasses, gloves, and a laboratory coat, avoid inhalation of vapours and contact with skin and eyes, keep containers closed when not in use to limit exposure to air and moisture, and dispose of residues and contaminated materials as chemical waste in accordance with institutional procedures. Always consult the current safety data sheet before use.
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