TCI
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Description
TCI E0772 Ethyl 4,4,4-Trifluorocrotonate is a fluorinated building block: an α,β-unsaturated ester carrying a trifluoromethyl group at the end of the chain. The structure combines two important elements at once — a conjugated carbonyl system that acts as a Michael acceptor, and a strongly electron-withdrawing CF₃ group. In the laboratory, this compound is used to introduce fluorinated fragments into the framework of target molecules, a strategy commonly applied in medicinal chemistry, agrochemical, and functional materials research, because the presence of fluorine can meaningfully alter the physicochemical properties of a molecule.
The characteristics that make this reagent a preferred choice are its high reactivity toward nucleophiles and its strong dienophilicity. The trifluoromethyl group lowers the electron density of the double bond, so conjugate addition by amines, thiols, carbanions, and other nucleophiles proceeds more readily than with an ordinary crotonate. On the other hand, the compound also serves as a good reactive partner in Diels–Alder reactions, 1,3-dipolar cycloadditions, and the formation of fluorinated rings. The ethyl ester group provides a route to further transformation into acids, amides, or alcohols.
In Indonesian laboratories, this reagent is typically used in university and institutional research settings where fluorinated fragments are built into target molecular frameworks — synthetic organic chemistry groups, medicinal chemistry and drug discovery programmes, agrochemical research, and functional materials development. Its liquid form allows it to be measured and transferred by syringe on a small scale, which suits the exploratory reaction work and multi-step synthesis routes commonly carried out in research laboratories.
Laboratory Applications
- Michael addition reactions: the conjugated carbonyl system combined with the electron-withdrawing CF₃ group makes conjugate addition by amines, thiols, and carbanions proceed more readily than with ordinary crotonate esters.
- Diels–Alder reactions: the electron-poor double bond makes this compound a strongly dienophilic partner, allowing cyclohexene frameworks bearing a trifluoromethyl substituent to be constructed in a single step.
- 1,3-Dipolar cycloadditions: the activated alkene serves as a reactive dipolarophile, giving access to five-membered heterocyclic rings that carry a fluorinated fragment in their structure.
- Synthesis of fluorinated ring systems: the reagent provides a direct route for building fluorinated rings, a recurring requirement in medicinal chemistry and agrochemical research programmes.
- Ester group transformations: the ethyl ester provides a handle for further conversion into the corresponding acids, amides, or alcohols, extending the range of accessible downstream derivatives.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- Product code: E0772
- CAS number: 25597-16-4
- Chemical name: Ethyl 4,4,4-Trifluorocrotonate
- Category: Chemistry > Building Blocks > Fluorinated Building Blocks
- Physical form: liquid
- Pack sizes: available in the pack sizes listed on the product page; please confirm the required size when ordering
- Storage: store in a cool, dry place in a tightly closed container
Handling and Storage
Store this reagent in a cool, dry, and well-ventilated place, away from heat sources, direct sunlight, and incompatible materials. Keep it in its original tightly closed container, or in a chemically resistant bottle with a secure cap, to prevent evaporation and moisture ingress; as a liquid α,β-unsaturated ester it should not be left open to the atmosphere. Handle the material in a fume hood, wearing safety glasses, chemically resistant gloves, and a laboratory coat. Transfer by syringe or pipette to minimise vapour exposure. Consult the manufacturer's Safety Data Sheet before use, and dispose of residues and contaminated materials through the laboratory's chemical waste procedure.
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