TCI
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Description
TCI D4737, CAS 5279-32-3, is 5,6-Dibromo-1,3-benzodioxole, a heterocyclic building block built from a benzene ring fused to a methylenedioxy group and carrying two adjacent bromine atoms. The 1,3-benzodioxole (methylenedioxybenzene) motif appears widely in natural products and bioactive molecules, which is why this scaffold is often a practical starting point for organic synthesis researchers. The presence of two neighbouring bromine atoms opens the way to constructing larger structures either stepwise or simultaneously, depending on the synthetic strategy chosen.
The property that makes this compound a preferred choice is the combination of an electron-rich aromatic framework with two closely spaced halide reaction sites. The methylenedioxy group acts as an electron donor while locking two oxygen atoms into a five-membered ring, making the framework rigid and geometrically well defined. The two bromine atoms, positioned ortho to one another, are highly useful for sequential cross-coupling reactions, benzyne generation, annulation cyclisations, and the construction of fused ring systems. This substitution pattern gives synthetic chemists considerable freedom in designing polycyclic frameworks from a single starting material.
In Indonesian laboratories, a building block of this kind is typically used by university research groups, graduate students, and institutional or industrial R&D units working on organic synthesis and medicinal chemistry. It suits work where a defined, ready-made heterocyclic core saves several preparative steps, allowing effort to be directed at the target molecule rather than at making the scaffold. Ordered in modest research quantities, it fits method development, route scouting, and small-scale exploratory synthesis programmes.
Laboratory Applications
- Sequential cross-coupling chemistry: the two ortho bromine atoms can be addressed one after the other, letting researchers install two different substituents on the same aromatic core in a controlled order.
- Benzyne precursor chemistry: adjacent halide positions on an activated aromatic ring make this substrate a convenient entry point for generating reactive aryne intermediates in cycloaddition studies.
- Annulation and cyclisation routes: the neighbouring reaction sites allow ring closure onto the benzodioxole core, giving direct access to fused polycyclic architectures from one starting material.
- Medicinal chemistry scaffold preparation: the methylenedioxybenzene motif recurs in natural products and bioactive molecules, so this block shortens routes toward analogue libraries and lead structures.
- Materials and ligand framework synthesis: the rigid, electron-rich, geometrically defined core serves as a predictable structural unit when building extended conjugated or polycyclic systems.
Specifications
- Brand: TCI
- CAS number: 5279-32-3
- Chemical name: 5,6-Dibromo-1,3-benzodioxole
- Product code: D4737
- Category: Chemistry > Building Blocks > Heterocyclic Building Blocks
- Pack sizes: available in standard TCI research pack sizes; please confirm the size you require when ordering
- Storage: keep in the original tightly closed container as indicated on the manufacturer's label
Handling and Storage
Store the material in its original tightly closed container, kept in a cool, dry, well-ventilated place away from direct sunlight, heat sources, and incompatible chemicals. Amber glass or the supplier's own packaging is suitable, since brominated aromatic compounds are best protected from light and moisture. Handle in a fume hood using nitrile gloves, safety goggles, and a laboratory coat, and avoid inhalation of dust or contact with skin and eyes. Keep containers clearly labelled, return them promptly to storage after weighing, and dispose of residues and contaminated consumables as halogenated organic waste in accordance with your institution's procedures. Always consult the manufacturer's Safety Data Sheet before use.
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