Chemical Identity and Structure

2-(p-Tolylethynyl)aniline consists of an aniline ring substituted at the ortho position with a para-tolyl-terminated alkyne chain. The molecule therefore combines two orthogonal reactive handles: a nucleophilic primary amine and an electrophilic-partner-reactive triple bond. This bifunctionality underpins its broad utility as a precursor in multi-step synthesis.

The internal alkyne geometry constrains rotation and positions the tolyl group in conjugation with the aniline π-system, a feature that can be exploited in the design of extended conjugated materials or fluorescent scaffolds. Molecular formula and exact molecular weight should always be verified against the batch Certificate of Analysis (CoA) supplied by Aladdin Scientific.

Research Applications

Heterocyclic synthesis: The amine and alkyne groups are ideally positioned for intramolecular cyclisation. Under transition-metal catalysis (e.g., gold, palladium, copper) or acid/base activation, 2-(arylethynyl)anilines are well-established precursors to indoles, isoquinolines, and related N-heterocycles. The para-methyl substituent on the tolyl ring can modulate electronic density and solubility.

Fluorescent and optoelectronic materials: The extended aromatic conjugation of tolylethynyl anilines makes them candidate monomers or end-caps for conjugated polymers, organic semiconductors, and fluorescence-based sensors. Photophysical properties should be determined experimentally for each target structure.

Bioorthogonal and click chemistry: The terminal-like reactivity of internal alkynes in strain-promoted or metal-catalysed cycloadditions provides access to triazole- or isoindole-containing pharmacophores relevant to medicinal chemistry programmes.

Safe Handling and Storage

General precautions: Aromatic amines as a chemical class may present health hazards including skin and eye irritation and potential sensitisation. Always consult the Safety Data Sheet (SDS) for the specific batch before use. Use appropriate personal protective equipment: nitrile gloves, safety glasses or goggles, and a laboratory coat. Handle in a well-ventilated fume hood.

Storage: Store in a tightly sealed container in a cool (typically 2–8 °C or as specified in the CoA), dry location protected from light and incompatible oxidising agents. If the compound is air- or moisture-sensitive, store under an inert gas (nitrogen or argon). Check the CoA for specific storage conditions for this batch.

Disposal: Dispose of residues in accordance with local regulations governing aromatic amine waste. Do not discharge into drains or the environment.

Ordering, Specification and Quality

2-(p-Tolylethynyl)aniline is available from Aladdin Scientific under SKU A727905. Each shipment is accompanied by a Certificate of Analysis confirming identity (typically by NMR and/or HPLC), purity, and physical appearance. Researchers are encouraged to request the CoA at the time of order to verify that the specification meets experimental requirements.

For bulk quantities, custom purity grades, or specific packaging requirements, contact Aladdin Scientific technical support or your regional sales representative. Pricing, available pack sizes, and current stock status can be confirmed through the Aladdin Scientific website or procurement portal.