372-29-2 | Ethyl 3-amino-4,4,4-trifluorocrotonate

CAS:372-29-2 | Ethyl 3-amino-4,4,4-trifluorocrotonate ,Description

Ethyl 3-amino-4,4,4-trifluorocrotonate (ETAC) is an organic compound with a wide range of applications in scientific research. It is a colorless liquid with a sweet odor, and is used in a variety of synthetic reactions. ETAC has been used in the synthesis of a variety of organic compounds, as well as in the production of pharmaceuticals and other materials. It is also used in the production of polymers, dyes, and in the production of biodegradable plastics.
 

Scientific Research Applications

Synthesis of Thiolation Products

Karimova et al. (2003) demonstrated that ethyl 4,4,4-trifluorocrotonate readily adds aliphatic and aromatic thiols in the presence of catalytic amounts of alkylamines, yielding 3-thiolation products. This reaction underscores the compound's utility in introducing sulfur-containing functional groups into organic molecules Karimova, N. M., Glazkov, A., Ignatenko, A. V., & Kolomiets, A. F. (2003).

Creation of Novel Uracils and Cytosines

Lutz and Hensen (1972) reported the conversion of ethyl 3-amino-4,4,4-trifluorocrotonate to novel 3-substituted-6-(trifluoromethyl)uracils through a one-step reaction with alkyl and aryl isocyanates. This synthesis path highlights the compound's role in generating new derivatives of uracil, a key component of RNA Albert W. Lutz and Trotto Susan Hensen (1972).

Development of New 4‐Trifluoromethylated 1,3‐Oxazin‐6‐Ones

Decock‐Plancquaert et al. (2010) synthesized new 4-trifluoromethyl-1,3-oxazin-6-ones from ethyl 3-amino-4,4,4-trifluorocrotonate, employing original procedures. This work illustrates the compound's utility in generating heterocyclic structures with potential applications in medicinal chemistry and material science Marie‐Aimée Decock‐Plancquaert, Evariste, F., Guillot, N., Janousek, Z., Maliverney, C., Merényi, R., & Viehe, H. (2010) .

Facile Synthesis of 1,4-Dihydropyridines

Sridhar and Perumal (2005) explored the use of ethyl 3-aminocrotonate in the synthesis of 4-pyrazolyl 1,4-dihydropyridines, highlighting an eco-benign, room-temperature process. This synthesis contributes to the broader field of heterocyclic chemistry, where 1,4-dihydropyridines have significant pharmacological relevance R. Sridhar & P. Perumal (2005).

Asymmetric Synthesis of Pyroglutamic Acids

Soloshonok et al. (1997) found that the Michael reaction between ethyl 4,4,4-trifluorocrotonate and a Ni(II) complex enables the asymmetric synthesis of (2S,3S)-3-trifluoromethylpyroglutamic acid. This method demonstrates the compound's role in producing stereochemically complex amino acids, which are valuable in drug development and biological studies Vadim A. Soloshonok, Avilov, Dimitry V., Kukhar, Valery P., Van Meervelt, Luc, & Mischenko, N. (1997).

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