4-Iodo-2-methylaniline, identified by CAS number 13194-68-8, is an aniline derivative carrying an iodine atom at the para position and a methyl group at the ortho position relative to the amino group. This arrangement of three substituents on a single aromatic ring makes it a highly useful non-heterocyclic building block for constructing substituted aromatic molecules in a directed manner. In organic synthesis laboratories, the compound serves as a starting point for building heterocyclic frameworks, azo dyes, ligands, and drug candidate compounds, because each functional group can be addressed at a different stage according to the synthetic strategy the researcher has designed.
The property that makes this material a frequent choice is the clear difference in reactivity between the nucleophilic amino group and the carbon–iodine bond, which is readily activated by palladium or copper catalysts. Researchers can perform cross-coupling at the iodine position while leaving the amino group intact, or conversely acylate and diazotize the amino group first. The methyl group at the ortho position exerts steric and electronic influences that are useful for directing regioselectivity, and at the same time forms part of the structure of many target molecules. Lot-to-lot quality consistency from TCI supports reproducible work across repeated preparations.
In Indonesian laboratories, this building block is typically used in university research groups, contract synthesis facilities, and industrial R&D units engaged in multi-step preparative organic chemistry. It is generally handled on small to moderate scale within fume hoods, where the sequential functionalization described above is carried out and monitored by routine analytical methods. Consistent supply of a defined grade allows research teams to repeat established routes without revalidating starting material behaviour at each attempt.
- Palladium-catalysed cross-coupling chemistry: the carbon–iodine bond is activated readily under palladium catalysis, letting researchers form new carbon–carbon or carbon–heteroatom bonds at the para position while the amino group remains untouched.
- Construction of heterocyclic frameworks: the combination of a free aromatic amine and an adjacent activated position provides the handles needed to close rings and assemble heterocyclic cores in multi-step synthetic sequences.
- Azo dye preparation: the nucleophilic amino group can be diazotized and coupled to suitable partners, giving access to azo compounds whose properties are further tuned by the iodine and methyl substituents.
- Ligand synthesis: the defined substitution pattern allows chemists to elaborate the aromatic ring into ligand scaffolds, with the ortho methyl group contributing the steric environment often required around a coordinating centre.
- Pharmaceutical candidate synthesis: as an intermediate for drug discovery work, it lets research teams introduce the substituted aryl motif early and then modify the amino and iodo positions at separate stages of the route.
| Brand | TCI (Tokyo Chemical Industry) |
|---|---|
| CAS number | 13194-68-8 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Non-Heterocyclic Building Blocks |
| Pack sizes | available in the catalogue pack sizes offered for this item; please confirm the required quantity when ordering |
| Physical form | — |
| Storage | store in a tightly closed container under the conditions stated on the manufacturer's label and safety data sheet |
- Product code: I0690
Store the container tightly closed in a cool, dry, well-ventilated area, away from direct sunlight, heat sources, and incompatible materials, following the conditions stated on the manufacturer's label and safety data sheet. Keep the material in its original supplier container, or in a chemically compatible, clearly labelled container with a secure closure if transferred. Handle inside a fume hood using appropriate personal protective equipment, including gloves, safety glasses, and a laboratory coat. Aromatic amines should be handled with care to avoid skin contact, inhalation of dust, and contamination of work surfaces. Return the container promptly to its designated storage location after weighing, and dispose of residues and contaminated consumables through the laboratory's established chemical waste procedures.
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