372-31-6 | Ethyl 4,4,4-trifluoroacetoacetate

CAS:372-31-6 | Ethyl 4,4,4-trifluoroacetoacetate ,Description

Ethyl 4,4,4-trifluoroacetoacetate (ETFA) is a versatile chemical compound that has a wide range of uses in scientific research and laboratory experiments. It is a colorless liquid that is soluble in organic solvents and has a distinct odor. ETFA is an important reagent in organic synthesis, used in the preparation of a variety of compounds, including pharmaceuticals, agrochemicals, and dyes. It is also used to catalyze a variety of reactions, as well as in the synthesis of polymers. In addition, ETFA is a useful intermediate in the production of fluorinated compounds. 
 

Scientific Research Applications

• Building Block for Enantiopure Chirons: ETFAA can be transformed into enantiopure chirons, which have both a trifluoromethyl group and an amino moiety. This process enables the creation of a series of trifluoromethyl-amino acids, crucial for pharmaceutical synthesis (Michaut, Metz, Paris, & Plaquevent, 2007).
• Addition of Thiols and Aminothiols: Ethyl 4,4,4-trifluorocrotonate, a derivative of ETFAA, reacts with thiols and aminothiols to yield 3-thiolation products. Such reactions are significant in the synthesis of sulfur-containing organic compounds (Karimova, Glazkov, Ignatenko, & Kolomiets, 2003).
• Synthesis of Trifluoromethylated Heterocyclic Compounds: ETFAA is used for synthesizing trifluoromethylated heterocyclic compounds under mild conditions. These compounds have potential applications in pharmaceuticals and other industries (朱仕正 et al., 2009) .
• Chemoselective Reactions with Anilines: Ethyl 4,4,4-trifluoroacetoacetate reacts with anilines to produce 2-trifluoromethyl-4- and 4-trifluoromethyl-2 quinolinones. This chemoselectivity is significant for synthesizing complex organic molecules (Berbasov & Soloshonok, 2003).
• Asymmetric Reduction in Organic Media: 1,4-butanediol promotes the asymmetric reduction of ETFAA to (S)-alcohol under water-deficient conditions. This method is useful for producing high-purity chiral alcohols (Zuhse, Leggewie, Hollmann, & Kara, 2015).
• Enantioselective Hydrogenation: ETFAA undergoes enantioselective hydrogenation with cinchona-modified platinum, allowing the synthesis of various trifluoromethyl alcohols with high enantiomeric excess (Arx, Mallát, & Baiker, 2000) .
• Brønsted-Acid-Catalyzed Enantioselective Arylation: ETFAA can undergo enantioselective arylation catalyzed by chiral phosphoric acid, leading to chiral trifluoromethyl compounds. This method is beneficial in asymmetric synthesis (Nie et al., 2009) .

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