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Description
TCI C2167, 3-Chloro-4-iodoaniline, is a substituted aniline compound carrying a primary amine group together with two different halogen atoms on the aromatic ring. It belongs to the class of non-heterocyclic building blocks, that is, aromatic starting materials used to assemble more complex target molecules. In the laboratory, this compound serves as a core scaffold in the synthesis of bioactive compounds, in the formation of amides and sulfonamides, and as a substrate in cross-coupling reactions used to construct carbon–carbon and carbon–nitrogen bonds.
The synthetic value of this compound lies in the presence of three functional groups whose reactivities complement one another. The iodine atom is the most reactive leaving group in palladium-catalysed oxidative addition, so that position can be selectively functionalised first through Suzuki, Sonogashira, or Heck reactions. The chlorine atom, far less reactive, remains in place as a structural marker or as a site for later reaction under more forcing conditions. The primary amine group, meanwhile, can be acylated, sulfonylated, diazotised, or used to form heterocyclic rings. This combination gives chemists considerable freedom in planning a synthetic route.
In Indonesian laboratories, materials of this type are typically used in university research groups, in organic and medicinal chemistry teaching laboratories, and in industrial research and development units working on the preparation of new compounds. The compound is normally purchased in small research quantities, handled inside a fume hood on a laboratory bench, and stored in a dedicated chemical cabinet together with other synthetic building blocks so that it remains ready for multi-step synthesis work.
Laboratory Applications
- Palladium-catalysed cross-coupling: the iodine atom undergoes oxidative addition readily, allowing selective Suzuki, Sonogashira, or Heck reactions at that position before the chlorine reacts.
- Synthesis of bioactive compounds: the aromatic scaffold with three complementary functional groups provides a practical starting point for building candidate molecules in medicinal chemistry research.
- Amide formation: the primary amine group can be acylated in a straightforward manner, making this compound a convenient aniline component for constructing amide linkages.
- Sulfonamide preparation: the same primary amine can be sulfonylated, giving access to sulfonamide derivatives that retain both halogen substituents on the ring.
- Heterocycle construction and diazotisation: the amine group can be diazotised or used to close heterocyclic rings, extending the compound into more elaborate ring systems.
Specifications
- Brand: TCI
- CAS number: 135050-44-1
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Chemical name: 3-Chloro-4-iodoaniline
- Product code: C2167
- Pack sizes: available in standard research-scale packaging as supplied by the manufacturer; storage in a cool, dry place away from light is recommended.
Handling and Storage
Store this compound in a cool, dry place, protected from direct sunlight and away from sources of heat or ignition. Keep it in its original tightly closed container, or in an equivalent chemical-resistant bottle with a well-sealing cap, and label it clearly. Halogenated anilines should be handled inside a fume hood with the sash at a safe working height. Wear nitrile gloves, safety goggles, and a laboratory coat, and avoid inhalation of dust as well as direct contact with skin and eyes. Keep the container separate from strong oxidising agents and strong acids, and collect any residues as chemical waste rather than disposing of them through the drain.
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