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Description
TCI D3577 2,6-Dibromo-4-methylaniline is a non-heterocyclic building block from TCI, supplied as an aniline derivative carrying two bromine atoms at the positions ortho to the amino group and one methyl group at the para position. This substitution pattern produces an aniline with a distinctive steric environment around the nitrogen. In the laboratory, the compound serves as a starting framework for constructing ligands, heterocyclic compounds, and target molecules, either through reactions at the amino group or by exploiting both bromine atoms as cross-coupling points.
The properties that make this material a preferred choice are the combination of amino-group nucleophilicity with the reactivity of the carbon–bromine bonds. The two ortho bromine atoms create steric hindrance that shields the nitrogen and controls product geometry, a characteristic that is particularly useful when designing bulky ligands for transition-metal catalysis. The amino group itself can be acylated, diazotized, condensed into imines, or used as a coupling partner in palladium-catalyzed amination. The methyl group at the para position contributes a weak electron-donating effect while also stabilizing the ring.
The compound is a solid at room temperature and is regarded as straightforward to handle, which suits the working conditions of Indonesian laboratories. It is typically weighed on an analytical balance and transferred into reaction vessels for synthesis work in university research groups, institutional research centers, and industrial development laboratories. Because it functions as an intermediate rather than a finished reagent system, it is normally purchased in the pack size that matches a planned series of synthetic steps.
Laboratory Applications
Bulky ligand synthesis: the two ortho bromine atoms shield the nitrogen centre and restrict rotation, allowing chemists to build sterically demanding ligands for transition-metal catalysis with predictable geometry.
Palladium-catalyzed cross-coupling: both carbon–bromine bonds act as reactive handles, so the ring can be functionalized at two defined positions to assemble larger aromatic frameworks.
Heterocycle construction: the amino group together with the adjacent bromine substituents provides the reactive arrangement needed to close rings and reach heterocyclic targets from a single starting material.
Imine and Schiff base preparation: condensation of the amino group with aldehydes or ketones proceeds directly, giving hindered imine products useful as intermediates or as ligand precursors.
Diazotization and acylation chemistry: the nucleophilic amino group can be diazotized or acylated to introduce further substituents, making the compound a flexible entry point in multi-step synthesis.
Specifications
Brand: TCI
CAS number: 6968-24-7
Catalogue reference: D3577
Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Physical form: solid at room temperature
Pack sizes: available in standard TCI catalogue pack sizes; please confirm the required size when ordering
Storage: keep in a closed original container in a cool, dry place away from light
Handling and Storage
Store TCI D3577 2,6-Dibromo-4-methylaniline in its original tightly closed container, kept in a cool, dry and well-ventilated place away from direct sunlight and sources of heat or ignition. Amber glass or the supplier's original packaging is suitable, and the container should be reclosed immediately after each weighing so the solid does not take up moisture. Handle the compound in a fume hood or a well-ventilated area, wearing safety glasses, gloves and a laboratory coat, and avoid contact with skin and eyes as well as inhalation of dust while transferring the solid. Use clean, dry spatulas to prevent cross-contamination, keep the material away from strong oxidizing agents, and label all secondary containers clearly. Always consult the manufacturer's Safety Data Sheet before use and follow local regulations for the disposal of chemical waste.
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