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Description
TCI E1501 Ethyl 4-Ethynylbenzoate is an aromatic compound that carries two strategically useful functional groups at once: a terminal alkyne and an ethyl ester positioned para to one another on the benzene ring. This combination makes it a highly sought-after building block in organic synthesis and materials chemistry laboratories, because the two groups can be reacted sequentially without interfering with each other. The terminal alkyne serves as an entry point to Sonogashira coupling reactions and click chemistry, while the ester group can be hydrolysed to a carboxylic acid to form amide bonds or to act as a connection point in metal-organic frameworks.
The characteristics that lead researchers to select this compound are the high yet controllable reactivity of the terminal alkyne, the linear geometry produced by the carbon-carbon triple bond, and the rigid aromatic backbone that supports the formation of conjugated structures. This rigid, linear character matters when researchers are constructing rod-shaped molecules for optoelectronic materials or symmetrical linkers for porous frameworks. The ester group is also a moderate electron-withdrawing substituent, so it influences the electron distribution of the conjugated system and can be exploited to tune both absorption and emission properties.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on organic synthesis, materials chemistry, and medicinal chemistry programmes. It is commonly drawn upon when a team needs a bifunctional aromatic intermediate for coupling work, for preparing conjugated systems, or for assembling framework linkers. Because it is supplied by TCI as a catalogue building block, it fits well into routine bench-scale synthetic workflows where a defined, ready-to-use starting material shortens the route to the target molecule.
Laboratory Applications
- Sonogashira cross-coupling reactions — the terminal alkyne reacts readily with aryl halides under palladium and copper catalysis, giving direct access to extended arylalkyne architectures while the ester remains untouched.
- Click chemistry and triazole formation — the terminal alkyne participates in cycloaddition with azides, making this compound convenient for building conjugates and libraries where the ester is retained for later modification.
- Metal-organic framework linker synthesis — after hydrolysis of the ethyl ester to the carboxylic acid, the rigid linear backbone functions as a connection point for assembling porous coordination frameworks.
- Conjugated and optoelectronic material preparation — the rigid aromatic core, linear triple bond and moderately electron-withdrawing ester together support rod-shaped conjugated systems with tunable absorption and emission behaviour.
- Amide bond construction in medicinal chemistry routes — ester hydrolysis yields a carboxylic acid handle for coupling to amines, allowing the alkyne to be preserved for a subsequent, orthogonal transformation.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- CAS number: 10602-03-6
- Chemical name: Ethyl 4-Ethynylbenzoate
- Catalogue code: E1501
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: available in TCI standard research-scale catalogue packs; please confirm the pack size required when ordering
- Storage: keep in a tightly closed original container in a cool, dry, well-ventilated place
Handling and Storage
Store the material in its tightly closed original container in a cool, dry and well-ventilated area, away from heat sources, direct sunlight and incompatible reagents such as strong oxidising agents. Amber glass or the supplier's original packaging is suitable for keeping the contents protected from light and moisture; close the container promptly after each use to limit exposure to air. Handle in a fume hood using safety goggles, chemical-resistant gloves and a laboratory coat, and avoid inhalation of vapours or contact with skin and eyes. Transfer with clean, dry glassware and consult the supplier safety data sheet before first use, particularly for detailed hazard, first-aid and waste disposal guidance.
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