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Description
TCI C2239 5-Chloro-2-iodoaniline is a multiply substituted aniline classified as a non-heterocyclic building block, and it occupies a special place in the synthetic chemist's toolbox. The molecule carries three functional handles on a single benzene ring at once: an amino group, a chlorine atom, and an iodine atom. This combination makes it a highly valuable starting material for constructing more elaborate ring systems, particularly heterocyclic compounds such as indoles, benzimidazoles, and quinoline derivatives that are widely encountered in bioactive molecules and functional materials.
The advantage that leads chemists to select this reagent lies in the difference in reactivity between the carbon–iodine and the carbon–chlorine bond. The C–I bond is far more readily cleaved under palladium-catalysed cross-coupling conditions, so researchers can direct the reaction exclusively to the iodine position while the chlorine atom remains intact as a reserve reactive site for a subsequent step. This property is known as orthogonal selectivity and is extremely valuable in stepwise synthesis. The amino group, positioned ortho to the iodine, also supplies exactly the right geometry for ring-closing reactions.
In Indonesian laboratories, this compound fits the working pattern of university research groups, institutional synthesis laboratories, and medicinal chemistry programmes that build heterocyclic scaffolds from defined intermediates. The 5 g pack matches the consumption pattern of a valuable reagent used at research scale, where a single campaign requires milligram-to-gram quantities rather than bulk material, and where a smaller pack keeps the reagent in good condition throughout the duration of a project.
Laboratory Applications
Palladium-catalysed cross-coupling: the C–I bond reacts preferentially under palladium catalysis, letting chemists functionalise the iodine position selectively while leaving the chlorine untouched.
Indole synthesis: the amino group ortho to iodine provides the correct geometry for ring closure, making this a direct entry point to indole frameworks.
Benzimidazole preparation: the free aniline nitrogen serves as the nucleophilic handle required to assemble benzimidazole ring systems from a single defined precursor.
Quinoline derivative construction: the substituted aniline core supplies both the nitrogen and the activated ring positions needed to build quinoline scaffolds efficiently.
Stepwise multi-stage synthesis: orthogonal selectivity between the two halogens allows sequential coupling steps, with the retained chlorine acting as a reserve reactive site later.
Specifications
Brand: TCI
CAS number: 6828-35-9
Catalogue code: C2239
Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack size: 5 g
Storage: keep in the tightly closed original container, protected from light and moisture
Handling and Storage
Store the material in its original tightly closed container in a cool, dry, well-ventilated place, protected from direct light and from moisture, and keep it separate from strong oxidising agents. Iodinated anilines are generally light-sensitive, so amber or otherwise light-protected glass containers are preferred, and the container should be reclosed promptly after each weighing. Handle the compound in a fume hood while wearing safety glasses, chemical-resistant gloves, and a laboratory coat, avoiding inhalation of dust and direct skin contact. Always consult the manufacturer's safety data sheet before use and dispose of residues in accordance with the laboratory's chemical waste procedures.
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