Description
(E)-4-(Dimethylamino)-1,1,1-trifluorobut-3-en-2-one, commonly abbreviated as MTFEO, is a specialized organic compound belonging to the class of trifluoromethylated enaminones. The “(E)-” prefix indicates a specific geometric isomer around the carbon-carbon double bond. This molecule features a dimethylamino group conjugated with an α,β-unsaturated ketone (enone) system, which is further substituted with a highly electronegative trifluoromethyl (CF3) group. The presence of the trifluoromethyl group significantly influences the compound’s reactivity, making the carbonyl carbon more electrophilic and the molecule a useful synthon for introducing trifluoromethyl moieties. MTFEO is typically encountered as a yellow to orange solid or oil and serves as a versatile building block in organic synthesis, particularly for constructing complex fluorinated molecules.
Properties
Property Value Chemical Name (E)-4-(Dimethylamino)-1,1,1-trifluorobut-3-en-2-one (MTFEO) CAS Number 127223-93-2 Molecular Formula C6H8F3NO Molecular Weight 167.13 g/mol Appearance Yellow to orange solid or oil (typical, may vary) Purity ≥97% (typical for synthetic intermediates) Melting Point Data not readily available; may be a low-melting solid or an oil at room temperature. Boiling Point Data not readily available; likely decomposes at higher temperatures or requires vacuum distillation. Solubility Soluble in most common organic solvents (e.g., dichloromethane, ethyl acetate, acetone, THF). Sparingly soluble in water. Stability Store in a cool, dry, dark place, preferably under an inert atmosphere. May be sensitive to strong acids, bases, or oxidizing agents. Usage
(E)-4-(Dimethylamino)-1,1,1-trifluorobut-3-en-2-one (MTFEO) is primarily utilized as a versatile intermediate and building block in organic synthesis. Its unique structure, combining an enaminone moiety with a trifluoromethyl group, makes it valuable for:
- Synthesis of Trifluoromethylated Heterocycles: MTFEO is a key precursor for creating a wide variety of trifluoromethyl-containing heterocyclic compounds, such as pyrazoles, pyridines, pyrimidines, and isoxazoles. These heterocycles are often scaffolds for biologically active molecules.
- Pharmaceutical Research: Used in the development of novel pharmaceutical drug candidates. The trifluoromethyl group can enhance properties like metabolic stability, lipophilicity, and binding affinity of drug molecules.
- Agrochemical Development: Employed in the synthesis of new pesticides (insecticides, fungicides, herbicides) where fluorine-containing compounds often exhibit enhanced efficacy.
- Reagent in Organic Reactions: It can participate in various reactions, including cycloadditions, Michael additions, and condensations, to form more complex fluorinated organic structures.
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