TCI I0593 Methyl 4-Iodobenzoate is the methyl ester of 4-iodobenzoic acid: a benzene ring carrying an ester group and an iodine atom directly opposite one another at the para positions. In synthetic organic laboratories, this compound is a very frequently used aromatic building block, most often as a cross-coupling substrate. Its role is to supply an aromatic ring bearing one highly reactive reaction site together with one functional group that can be elaborated later, arranged in a linear geometry that makes it well suited to constructing extended molecules such as pharmaceutical intermediates, molecular probes, and ligands for porous materials.
The principal advantage of this material lies in the reactivity of the carbon-iodine bond. Among all aryl halides, iodoarenes undergo oxidative addition to palladium or copper centres most readily, which allows coupling reactions to proceed at lower temperatures, with smaller catalyst loadings, and over shorter reaction times. Those milder conditions are especially valuable when other substrates in the mixture are fragile. The para substitution pattern gives a sterically clean outcome, since no neighbouring substituent obstructs the approach of the catalyst, so conversions are typically high and the product profile is predictable.
In Indonesian laboratories, this building block is used in university and institutional research groups working on organic synthesis, medicinal chemistry, and materials chemistry, as well as in industrial R&D units developing pharmaceutical intermediates. It is normally handled at small to moderate scale on the bench, weighed out for coupling reactions and subsequent functional-group transformations of the ester. Because it is supplied as a defined research chemical from TCI, it also serves as a dependable reference substrate when methods are being developed or reproduced.
- Palladium-catalysed cross-coupling reactions, where the highly reactive carbon-iodine bond undergoes oxidative addition readily and allows the coupling to run under comparatively mild conditions.
- Copper-mediated coupling chemistry, in which iodoarenes are the preferred halide partner because they react faster and more cleanly than the corresponding bromides or chlorides.
- Synthesis of pharmaceutical intermediates, where the linear para arrangement of the two functional handles supports the stepwise construction of extended drug-like molecular frameworks.
- Preparation of molecular probes, since the ester group can be transformed after the coupling step to attach reporter units or linkers without disturbing the aromatic core.
- Construction of ligands for porous materials, where the para geometry provides the rigid, linear connectivity required for building framework-type architectures from aromatic units.
| Brand | TCI (Tokyo Chemical Industry) |
|---|---|
| CAS number | 619-44-3 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Non-Heterocyclic Building Blocks |
| Pack sizes | available in the standard research-scale pack sizes offered by TCI for this catalogue item; storage in a cool, dry place as indicated on the manufacturer's label. |
| Physical form | — |
| Storage | — |
- Product code: I0593
- Chemical name: Methyl 4-Iodobenzoate
Store the container tightly closed in a cool, dry, well-ventilated place away from direct sunlight, heat sources, and incompatible materials, following the storage conditions stated on the manufacturer's label and safety data sheet. Keep the material in its original supplier container or in a clean, chemically compatible, clearly labelled vessel, and close it immediately after weighing to limit moisture ingress. Handle it in a fume hood using safety glasses, gloves, and a laboratory coat, avoid the generation of dust, and wash hands after use. Dispose of residues and contaminated consumables through the institution's chemical waste procedures.
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