TCI B6090 is 1-Benzyl-5-bromo-1H-indole, an indole derivative whose nitrogen has been benzylated and which carries a bromine atom at position 5 of the benzene ring. Indole is one of the most important heterocyclic frameworks in organic chemistry, appearing in the amino acid tryptophan, in the hormones serotonin and melatonin, and in thousands of natural product alkaloids and synthetic drugs. In practical laboratory work this material serves as a pre-arranged building block, allowing chemists to start directly from a substituted indole framework without first carrying out the time-consuming benzylation and bromination steps themselves.
The property that makes this compound valuable is the presence of two complementary structural features. The benzyl group on the nitrogen acts as both a protecting group and a solubility modifier, preventing unwanted reactions at the indole N-H during the course of a transformation, and it can be removed by hydrogenolysis when required. The bromine atom at position 5 is an ideal connection point for palladium-catalysed cross-coupling reactions, including Suzuki-Miyaura, Sonogashira, Heck, and Buchwald-Hartwig amination, so that researchers can attach new groups regioselectively. Position 3 of the indole ring remains free for electrophilic functionalisation, which means a single starting material can be elaborated along two independent directions.
In Indonesian laboratories this building block is used mainly in university and institutional research groups working on medicinal chemistry, natural product synthesis, and materials based on heterocycles. Because it removes two preparative steps from a synthetic route, it is particularly useful for graduate research and thesis work where reaction time and reagent budgets are limited. It is generally ordered in small research quantities and handled within a standard organic synthesis laboratory equipped with a fume hood, rotary evaporator, and column chromatography facilities.
- Suzuki-Miyaura cross-coupling: the 5-bromo substituent reacts cleanly with aryl and heteroaryl boronic acids under palladium catalysis, giving biaryl indoles in a single regioselective step.
- Buchwald-Hartwig amination: the carbon-bromine bond at position 5 allows direct introduction of primary and secondary amines, a common requirement when building indole-based pharmacophores for screening.
- Sonogashira and Heck couplings: the aryl bromide serves as the electrophilic partner for installing alkyne or alkene side chains, extending conjugation for photophysical and materials-oriented studies.
- Medicinal chemistry scaffold elaboration: the protected nitrogen lets chemists functionalise position 3 electrophilically first, then unmask the N-H later by hydrogenolysis of the benzyl group.
- Natural product and alkaloid synthesis: the pre-substituted indole framework shortens multi-step routes toward tryptophan, serotonin, and melatonin analogues studied in academic research programmes.
| Brand | TCI (Tokyo Chemical Industry) |
|---|---|
| CAS number | 10075-51-1 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Heterocyclic Building Blocks |
| Pack sizes | available in research-scale pack sizes; please confirm the currently listed options when ordering |
| Physical form | — |
| Storage | keep in a cool, dry place in the original tightly closed container |
- Chemical name: 1-Benzyl-5-bromo-1H-indole
Store the container tightly closed in a cool, dry, well-ventilated area away from direct sunlight, heat sources, and strong oxidising agents. The original supplier container is the most suitable storage vessel; if transfer is necessary, use clean amber glass with a chemically resistant closure and label it clearly with the name and CAS number. Handle all weighing and transfer operations inside a fume hood, wearing safety goggles, nitrile gloves, and a laboratory coat. Avoid inhalation of dust and contact with skin and eyes. Keep the container closed when not in use to limit moisture uptake, and dispose of residues and contaminated consumables as halogenated organic chemical waste in accordance with institutional procedures. Always consult the manufacturer's safety data sheet before first use.
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