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Description
TCI E1471 Ethyl (E)-3-(p-Tolyl)acrylate is a cinnamate ester bearing a methyl substituent at the para position of the aromatic ring, supplied by TCI as a non-heterocyclic building block with defined double-bond geometry fixed as the E isomer. In the laboratory it serves as a Michael acceptor and as a conjugated olefin substrate, allowing researchers to construct aryl–alkene frameworks in a controlled manner. Because the E configuration is clearly defined, the material functions both as a starting material and as a comparison standard in stereochemical studies, since any change in geometry during a reaction can be followed unambiguously by routine spectroscopic analysis.
The property that makes this compound a preferred choice is its balance between reactivity and stability. The double bond conjugated to the ester group is electrophilic at the beta position, so it readily accepts nucleophiles and participates in hydrogenation, cyclopropanation, epoxidation, dihydroxylation, and cycloaddition reactions. At the same time, the methyl group on the aromatic ring contributes a mild electron-donating effect that slightly reduces the electrophilicity of the system, making reactions easier to control than with analogues carrying strongly electron-withdrawing substituents. This moderated reactivity translates into cleaner conversions and fewer competing side reactions during optimisation work.
In Indonesian laboratories, this building block is typically used in synthetic organic chemistry groups at universities and in research institutes carrying out methodology development, asymmetric catalysis screening, and the preparation of intermediates for further functionalisation. Its well-defined stereochemistry makes it convenient for teaching and training work on alkene reactivity, while its predictable behaviour suits routine bench-scale reaction trials where consistent, reproducible starting material quality is expected from a recognised supplier.
Laboratory Applications
- Michael addition chemistry — the conjugated ester provides an electrophilic beta carbon that accepts a wide range of nucleophiles, giving researchers a reliable acceptor for carbon–carbon and carbon–heteroatom bond formation studies.
- Stereochemical reference work — the defined E configuration allows any isomerisation or geometric change occurring during a reaction to be detected clearly through routine spectroscopic comparison against the starting material.
- Cyclopropanation and epoxidation studies — the activated alkene readily undergoes carbene and oxygen transfer, making this ester a convenient substrate for evaluating reagent systems and catalyst performance on conjugated olefins.
- Catalytic hydrogenation investigations — the conjugated double bond can be reduced selectively, so the compound serves well for comparing catalyst activity, selectivity, and reaction conditions across hydrogenation methodology experiments.
- Cycloaddition and dihydroxylation research — the electron-moderated aryl alkene participates in cycloaddition and oxidative functionalisation routes, supporting the controlled construction of more elaborate substituted frameworks from a simple starting material.
Specifications
- Brand: TCI
- CAS number: 24393-49-5
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Product code: E1471
- Pack sizes: available in standard TCI catalogue pack sizes; please confirm the size required when ordering
- Storage note: store in a tightly closed original container, protected from light and heat, in accordance with the supplier documentation
Handling and Storage
Store the container tightly closed in a cool, dry, and well-ventilated area, away from direct sunlight, heat sources, and ignition sources. Keep the material in its original supplier packaging or in a compatible, clearly labelled chemical container, and avoid contact with strong oxidising agents and strong nucleophiles or bases that could react with the activated ester system. Handle in a fume hood using safety glasses, gloves, and a laboratory coat, and avoid inhalation of vapours or contact with skin and eyes. Reseal the container promptly after use, and always consult the supplier safety data sheet before handling, transfer, or disposal.
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