tert-Butyl 5-Bromo-1H-indole-1-carboxylate is an indole derivative whose nitrogen atom is protected by a tert-butoxycarbonyl (Boc) group and whose benzene ring carries a bromine atom at the 5-position. Indole is one of the most important heterocyclic scaffolds in medicinal chemistry, forming the core of tryptophan, serotonin, and a large number of natural alkaloids. In the synthesis laboratory, this compound serves as a versatile building block that provides a reactive attachment point in the form of a carbon-bromine bond, ready to be used for assembling more complex molecules through cross-coupling reactions.
The advantage of this material lies in the Boc protection, which deactivates the indole nitrogen while simultaneously lowering the electron density of the ring. Without this protection, the weakly acidic and nucleophilic indole nitrogen can interfere with metal catalysts and trigger side reactions at the highly reactive C-3 position. The Boc group also improves solubility in non-polar organic solvents and simplifies purification by column chromatography. Once the coupling step is complete, this protecting group can be removed with acid or by heating without disturbing the structure that has been built, making the strategy temporary and reversible by design.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on organic synthesis and medicinal chemistry, as well as in pharmaceutical research and development units exploring new heterocyclic scaffolds. It is normally handled at milligram to gram scale on the synthetic bench, where the bromide handle and the protected nitrogen let researchers plan multi-step routes with predictable selectivity and straightforward workup.
- Suzuki-Miyaura cross-coupling: the aryl bromide at the 5-position provides a clean oxidative addition site for palladium catalysts, while the Boc-protected nitrogen keeps the catalyst free from interference by the acidic indole N-H.
- Buchwald-Hartwig amination: the carbon-bromine bond allows direct installation of nitrogen substituents at the 5-position, giving access to aminoindole frameworks that are common targets in medicinal chemistry programmes.
- Medicinal chemistry scaffold elaboration: because indole forms the core of tryptophan, serotonin, and many natural alkaloids, this protected bromoindole serves as a convenient entry point for building biologically oriented analogue series.
- Multi-step synthetic route development: the Boc group can be removed later with acid or heating without disturbing the structure already assembled, so chemists can sequence transformations without redesigning the protection strategy.
- Chromatographic purification workflows: the Boc group raises solubility in non-polar organic solvents and improves behaviour on silica, making intermediates easier to isolate cleanly by column chromatography during method development.
| Brand | TCI |
|---|---|
| CAS number | 182344-70-3 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Heterocyclic Building Blocks |
| Pack sizes | available in the catalogue pack sizes offered by TCI for this product code |
| Physical form | — |
| Storage | store in a cool, dry place in a tightly closed container, away from light and moisture |
- Product code: B6358
Store the material in its original tightly closed container in a cool, dry, well-ventilated area, protected from light, moisture, and sources of heat or ignition. Amber glass or the supplier's original packaging is suitable; keep the closure sealed between uses to limit exposure to atmospheric moisture. Handle in a fume hood using safety glasses, chemical-resistant gloves, and a laboratory coat, and avoid generating dust when weighing. Keep away from strong acids, since acidic conditions remove the Boc protecting group. Consult the manufacturer's safety data sheet before use and dispose of residues through the laboratory's chemical waste procedure.
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