Cas no 1048670-08-1 (ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate)

Ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate is a fluorinated β-keto ester derivative with significant utility in synthetic organic chemistry. Its trifluoromethyl group enhances electrophilic reactivity, making it a valuable intermediate for constructing trifluoromethyl-substituted heterocycles and other fluorinated compounds. The ethoxymethylene moiety further increases its versatility in condensation and cyclization reactions. This compound is particularly useful in the synthesis of pharmaceuticals, agrochemicals, and specialty materials due to its ability to introduce trifluoromethyl groups efficiently. Its stability under standard conditions and compatibility with various reaction conditions contribute to its broad applicability in research and industrial processes.
ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate structure
1048670-08-1 structure
Product Name:ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate
CAS No:1048670-08-1
MF:C9H11F3O4
MW:240.176453828812
CID:2875207
PubChem ID:2737179
Update Time:2025-05-26

ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate Chemical and Physical Properties

Names and Identifiers

    • ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate
    • .ethyl (ethoxymethylene)trifluoroacetoacetate;ethyl 2-ethoxymethylene-4,4,4-trifluoro-3-oxobutanoate;.2-[1-ethoxymethylidene]-4,4,4-trifluoro-3-oxobutyric acid ethyl ester;.ethyl 2-(ethoxymethylidene)-4,4,4-trifluoro-3-oxobutanoate;.ethyl (2Z)-3-(ethyloxy)-2-(trifluoroacetyl)-2-propenoate;
    • Ethyl ethoxymethylene-3-oxo-4,4,4-trifluoro-butyrate
    • BBL102357
    • ethyl 3-ethoxy-2-(2,2,2-trifluoroacetyl)acrylate
    • MFCD00052716
    • (Z)-ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate
    • ethyl 2-ethoxy-methylidene-4,4,4-trifluoro-3-oxobutanoate
    • Ethyl (2Z)-2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate
    • ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobu
    • AS-43173
    • 571-55-1
    • CS-0144903
    • 1048670-08-1
    • (Z)-ethyl2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate
    • AKOS005256283
    • ethyl (Z)-2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate
    • Ethyl 2-(ethoxymethylene)-4,4,4-trifluoroacetoacetate
    • ethyl (2Z)-2-(ethoxymethylidene)-4,4,4-trifluoro-3-oxobutanoate
    • STL556157
    • ethyl ethoxymethylene-3-oxo-4,4,4-trifluorobutyrate
    • SCHEMBL5188862
    • Inchi: 1S/C9H11F3O4/c1-3-15-5-6(8(14)16-4-2)7(13)9(10,11)12/h5H,3-4H2,1-2H3/b6-5-
    • InChI Key: XNGGOXOLHQANRB-WAYWQWQTSA-N
    • SMILES: FC(C(/C(=C/OCC)/C(=O)OCC)=O)(F)F

Computed Properties

  • Exact Mass: 240.06100
  • Monoisotopic Mass: 240.06094331Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 7
  • Complexity: 294
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.1
  • Topological Polar Surface Area: 52.6?2

Experimental Properties

  • PSA: 52.60000
  • LogP: 1.60130

ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate Pricemore >>

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Additional information on ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate

Recent Advances in the Application of Ethyl 2-(Ethoxymethylene)-4,4,4-Trifluoro-3-Oxobutanoate (CAS: 1048670-08-1) in Chemical Biology and Pharmaceutical Research

Ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate (CAS: 1048670-08-1) is a fluorinated β-keto ester derivative that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical synthesis. This compound serves as a key intermediate in the preparation of various heterocyclic compounds, particularly those with potential biological activities. Recent studies have explored its utility in the synthesis of trifluoromethyl-substituted pyrazoles, isoxazoles, and other nitrogen-containing heterocycles, which are of great interest in drug discovery programs targeting inflammation, cancer, and infectious diseases.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's effectiveness as a building block for the synthesis of novel trifluoromethylated pyrazole derivatives with potent COX-2 inhibitory activity. The researchers utilized ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate as a starting material in a one-pot cyclocondensation reaction with hydrazine derivatives, achieving excellent yields of the target compounds. Molecular docking studies revealed that the trifluoromethyl group significantly enhanced binding affinity to the COX-2 active site, suggesting potential for developing new anti-inflammatory agents.

In the field of antimicrobial research, a recent publication in Bioorganic & Medicinal Chemistry Letters (2024) reported the use of this compound in the synthesis of novel quinolone derivatives with enhanced activity against drug-resistant bacterial strains. The presence of the trifluoromethyl group was found to improve membrane permeability and target binding, while the ethoxymethylene moiety contributed to metabolic stability. These findings highlight the compound's potential in addressing the growing challenge of antibiotic resistance.

From a synthetic chemistry perspective, advances in catalytic methods have improved the efficiency of reactions involving ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate. A 2023 study in Advanced Synthesis & Catalysis described a novel copper-catalyzed coupling reaction that enables the direct functionalization of this compound at the β-position, opening new avenues for structural diversification. This methodological breakthrough has significant implications for medicinal chemistry, allowing for more efficient exploration of structure-activity relationships in drug discovery programs.

Ongoing research continues to explore the full potential of this versatile building block. Current investigations focus on its application in the synthesis of PROTACs (proteolysis targeting chimeras) and other targeted protein degradation technologies, where the trifluoromethyl group may offer advantages in terms of protein binding and pharmacokinetic properties. As the pharmaceutical industry increasingly embraces fluorine-containing compounds for their beneficial effects on drug properties, ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate is poised to play an important role in the development of next-generation therapeutics.

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