5-Chlorooxindole is a heterocyclic compound built on the oxindole framework — an indole bearing a carbonyl group at the 2-position — with a chlorine substituent at the 5-position. In the laboratory, this compound serves as a highly valued starting material in organic synthesis and medicinal chemistry, particularly because the oxindole scaffold forms the structural core of a number of bioactive compounds and natural products. It is typically used as an entry point for constructing more complex molecules through condensation reactions or through functionalisation at the active carbon position adjacent to the carbonyl group.
The characteristic that makes 5-Chlorooxindole such a frequent choice is the presence of the C-3 position, which is weakly acidic because it sits between the carbonyl group and the aromatic ring. This position is readily deprotonated and then reacted with aldehydes via Knoevenagel condensation to give 3-alkylideneoxindole derivatives, a motif widely recognised in the development of kinase enzyme inhibitors. The cyclic amide group on the five-membered ring supplies both a hydrogen-bond donor and an acceptor at once, a property that is valuable in molecular design. The chlorine atom at the 5-position opens the door to further modification in subsequent synthetic steps.
In Indonesian laboratories, 5-Chlorooxindole is generally found in university and institutional research settings where synthetic organic chemistry and medicinal chemistry work is carried out. It is typically drawn upon by research groups preparing heterocyclic derivative libraries, by graduate students running multi-step synthesis projects, and in method development work where a reliable, well-defined building block is required as the starting point for a reaction sequence. Its role is that of a foundation material rather than a finished reagent.
- Knoevenagel condensation with aldehydes — the weakly acidic C-3 position is easily deprotonated and couples cleanly with aldehyde partners to deliver 3-alkylideneoxindole products in a single step.
- Kinase inhibitor discovery chemistry — the 3-alkylideneoxindole motif accessible from this material is a well-established structural class in the development of enzyme inhibitor candidates for medicinal chemistry programmes.
- Heterocyclic building block for multi-step synthesis — the oxindole core provides a defined starting scaffold from which more complex target molecules can be assembled through successive functionalisation steps.
- Bioactive compound and natural product analogue synthesis — because the oxindole framework forms the structural core of many natural products, this material offers a direct entry route into analogue preparation.
- Further derivatisation at the halogenated position — the chlorine atom at the 5-position provides a handle for subsequent modification, allowing systematic variation of substituents around the aromatic ring.
| Brand | TCI |
|---|---|
| CAS number | 17630-75-0 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Heterocyclic Building Blocks |
| Pack sizes | available in standard TCI research-scale packaging; please confirm the size required when ordering |
| Physical form | — |
| Storage | keep in the closed original container under the conditions stated on the manufacturer's label |
- Product code: C1509
- Chemical name: 5-Chlorooxindole
Store 5-Chlorooxindole in its original tightly closed container in a cool, dry and well-ventilated area, away from direct sunlight, heat sources and incompatible chemicals. Amber glass or the supplied manufacturer packaging is suitable for keeping the material protected from light and moisture. Handle the compound in a fume hood using standard personal protective equipment — laboratory coat, safety glasses and chemical-resistant gloves — and avoid generating or inhaling dust when weighing out portions. Close the container promptly after use to limit exposure to atmospheric moisture. Always consult the manufacturer's Safety Data Sheet before use, and follow institutional procedures for the disposal of chemical waste.
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