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Description
TCI E1548 1-(4-Methoxyphenyl)prop-2-yn-1-ol is an aromatic propargylic alcohol that carries a hydroxyl group on the benzylic carbon together with a terminal triple bond at the adjacent position, on a benzene ring substituted with a methoxy group at the para position. In the organic synthesis laboratory, this compound serves as a versatile building block because it presents three reactive handles at once: a hydroxyl group that can be converted into a leaving group, a terminal alkyne that can be coupled or activated by metal catalysts, and an electron-rich aromatic ring that stabilises cationic intermediates as the reaction proceeds.
The property that makes this compound a preferred choice is the ease with which it forms a stabilised propargylic cation. The electron-donating methoxy group at the para position significantly stabilises the positive charge on the benzylic carbon, so propargylic substitution reactions proceed under mild catalytic conditions without requiring harsh reagents. Its terminal alkyne simultaneously acts as a handle for Sonogashira coupling, azide–alkyne cycloaddition, and rearrangement into enones via the Meyer–Schuster pathway. The presence of a chiral centre at the carbinol carbon further broadens its value in stereoselective work.
In Indonesian laboratories, this building block is typically used in university research groups, synthetic methodology laboratories, and medicinal chemistry programmes that assemble more complex molecular frameworks from small, well-defined fragments. It is normally handled at bench scale for the preparation of intermediates, for exploratory route development, and for catalyst screening studies, where a compound offering several orthogonal reactive sites lets a single starting material support a range of different transformations.
Laboratory Applications
- Propargylic substitution reactions — the para-methoxy group stabilises the propargylic cation intermediate, allowing nucleophiles to be introduced under mild catalytic conditions rather than forcing conditions.
- Sonogashira cross-coupling — the terminal alkyne provides a direct handle for palladium- and copper-mediated coupling with aryl or vinyl halides to extend the carbon framework.
- Azide–alkyne cycloaddition (click chemistry) — the terminal triple bond reacts reliably to build triazole units, while the free hydroxyl remains available for later functionalisation steps.
- Meyer–Schuster rearrangement — the propargylic alcohol motif rearranges into the corresponding enone, giving synthetic access to conjugated carbonyl systems from a single precursor.
- Stereoselective methodology development — the chiral carbinol carbon makes this substrate useful for testing asymmetric catalysts and evaluating enantioselectivity in new transformations.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- Product code: E1548
- CAS number: 19115-30-1
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: available in standard TCI research-scale packaging; please confirm the size required when ordering
- Storage: keep in a cool, dark place in a tightly closed container
Handling and Storage
Store the container tightly closed in a cool, dark, well-ventilated place, away from heat, direct sunlight, and sources of ignition, and separated from strong oxidising agents and strong acids. Keep the material in its original supplier container or in a compatible, clearly labelled glass container with a secure closure. Handle inside a fume hood, wearing safety goggles, chemical-resistant gloves, and a laboratory coat, and avoid inhalation of vapour or contact with skin and eyes. Minimise exposure to air and moisture by closing the container promptly after use, and consult the manufacturer's safety data sheet before handling, use, or disposal.
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