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Description
1-(4-Ethynylphenyl)ethan-1-one, also known as 4'-ethynylacetophenone, is an aromatic building block that carries two different functional groups positioned para to one another: a terminal ethynyl group and a methyl ketone group. The presence of two reaction handles with distinct reactivity makes this compound highly useful in stepwise synthesis, because researchers can transform one group without disturbing the other. In the laboratory, a material of this kind serves as an efficient starting point for constructing more complex target molecules without having to build the aromatic framework from scratch.
The property that makes this compound a preferred choice is its complementary bifunctional character. The terminal alkyne group is ready for use in Sonogashira coupling, click reactions with azides, and alkyne polymerisation, while the acetyl group is a classic carbonyl that can be reduced to an alcohol, condensed into a chalcone, or converted into a heterocyclic ring through various condensation reactions. The ketone group is also electron-withdrawing, so it influences the electron density of the aromatic ring and imparts useful electronic character to conjugated materials. This push-pull combination gives the molecule value well beyond that of a simple intermediate.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on organic synthesis, medicinal chemistry, and functional materials. It suits teams that prepare compound libraries, that need a reliable para-substituted scaffold for coupling chemistry, or that develop conjugated systems for materials studies. Because it is supplied as a catalogue reagent from TCI, it fits research workflows that require consistent, repeatable starting materials across successive synthetic campaigns.
Laboratory Applications
- Sonogashira cross-coupling: the terminal alkyne couples directly with aryl or vinyl halides under palladium and copper catalysis, extending the conjugated framework while the acetyl group remains untouched.
- Click chemistry with azides: the terminal ethynyl handle undergoes cycloaddition with organic azides to form triazole linkages, making the compound useful for bioconjugation and modular library assembly.
- Chalcone synthesis: the methyl ketone condenses readily with aromatic aldehydes under aldol conditions, giving alkyne-functionalised chalcones that can be elaborated further at the ethynyl position.
- Heterocycle construction: the acetyl group can be converted into pyrazole, pyrimidine, and related ring systems through standard condensation routes, providing rapid access to nitrogen heterocyclic scaffolds.
- Conjugated and functional materials: alkyne polymerisation together with the electron-withdrawing ketone produces push-pull electronic character valued in the preparation of conjugated polymers and other functional materials.
Specifications
- Brand: TCI, catalogue reference E1563
- CAS number: 42472-69-5
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Chemical name: 1-(4-Ethynylphenyl)ethan-1-one, also known as 4'-ethynylacetophenone
- Pack sizes: available in standard TCI research-scale catalogue pack sizes; please confirm the pack size when ordering
- Storage: store in a tightly closed container in a cool, dark, well-ventilated place
Handling and Storage
Store this reagent in a tightly closed original container in a cool, dark and well-ventilated area, away from heat sources, direct sunlight, ignition sources and strong oxidising agents. Terminal alkynes and reactive carbonyl compounds are best kept sealed to limit exposure to air and moisture, so reclose the container promptly after each use. Handle the material inside a fume hood, wearing safety goggles, chemical-resistant gloves and a laboratory coat, and avoid inhalation of vapours or contact with skin and eyes. Consult the manufacturer's safety data sheet before use, and dispose of residues and contaminated materials according to institutional chemical waste procedures.
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