337-82-6 | Ethyl2,2,3,3-tetrafluoropropionate

CAS:337-82-6 | Ethyl2,2,3,3-tetrafluoropropionate,Description

Ethyl 2,2,3,3-tetrafluoropropanoate is a chemical compound that is part of a broader class of organofluorine compounds, which are characterized by the presence of fluorine atoms in their molecular structure. These compounds are of significant interest due to their unique physical and chemical properties, which make them useful in various applications, including pharmaceuticals, agrochemicals, and materials science.

Synthesis Analysis

The synthesis of related fluorinated compounds has been explored in several studies. For instance, ethyl 3,3,3-trifluoropropionate was synthesized from commercially available 2-bromo-3,3,3-trifluoropropene, which underwent a reaction with bromine followed by treatment with potassium ethoxide, yielding the product in 60% overall yield in two steps. Another synthesis approach involved the reaction of ethyl 2-(trifluoromethyl) propanoate to produce 3,3-difluoro-2-methylacrylate (DFMA) with yields ranging from 70 to 90%. These methods demonstrate the feasibility of synthesizing fluorinated esters through various chemical pathways.

Molecular Structure Analysis

The molecular structure of fluorinated compounds can be quite complex. For example, the structural characterization of 2,2,3,3-tetrakis(trifluoromethanesulfonato)tetrasilanes revealed a distorted octahedral coordination of the two central silicon atoms due to Si···O interactions. Although this compound is not ethyl 2,2,3,3-tetrafluoropropanoate, it provides insight into the potential complexity of fluorinated molecular structures and the types of analyses that can be conducted to understand their geometry.

Chemical Reactions Analysis

Fluorinated compounds can participate in a variety of chemical reactions. The 1,3-dipolar cycloadditions of ethyl 2-diazo-3,3,3-trifluoropropanoate with alkynes and subsequent rearrangements led to the formation of CF3-substituted pyrazoles. Additionally, the cross-tetramerization of tetrafluoroethylene, alkynes, and ethylene in the presence of a nickel catalyst resulted in the formation of 1,3-dienes with a tetrafluorobutyl chain. These reactions highlight the reactivity of fluorinated esters and their potential to form diverse products.

Physical and Chemical Properties Analysis

The physical and chemical properties of fluorinated compounds are influenced by the presence of fluorine atoms. For instance, the addition of thioacetic acid to ethyl 2-(α-hydroxyhexafluoroisopropyl)acrylate occurs at 20°C, while reactions with thiols require higher temperatures and are accelerated by acid catalysts. The radical addition of CF2BrCl or CF2Br2 to ethyl vinyl ether, leading to the synthesis of ethyl 3,3,3-trifluoropropanoate and its 2-bromo derivative, also reflects the unique reactivity of these compounds. The fluorine atoms can significantly alter the chemical reactivity and stability of the molecules, affecting their synthesis and applications.

Scientific Research Applications

Application in Agrochemical and Pharmaceutical Industries

• Summary of the Application: Ethyl 2,2,3,3-tetrafluoropropanoate is used in the synthesis of trifluoromethylpyridines, which are key structural motifs in active agrochemical and pharmaceutical ingredients. Trifluoromethylpyridine (TFMP) derivatives are primarily used in crop protection from pests.
• Results or Outcomes: Over 20 new TFMP-containing agrochemicals have acquired ISO common names. Additionally, five pharmaceutical and two veterinary products containing the TFMP moiety have been granted market approval, and many candidates are currently undergoing clinical trials.

Application in High Voltage Electrolytes

• Summary of the Application: Ethyl 2,2,3,3-tetrafluoropropanoate is used in the synthesis of 1,1,2,2-tetrafluoroethyl-2,2,3,3-tetrafluoropropyl ether (F-EPE), which is investigated as a cosolvent for high voltage electrolytes of Li2CoPO4F. This is particularly important for the development of high energy density lithium ion batteries.
• Methods of Application or Experimental Procedures: The F-EPE/DMC electrolyte possesses both a high oxidation voltage up to 6.2 V vs. Li+/Li on Pt electrode and superior oxidation stability on Li2CoPO4F cathode. The high stability of F-EPE/DMC electrolyte effectively inhibits the oxidative decomposition of the electrolyte on Li2CoPO4F electrode above 5.0 V and suppresses the damage to the surface of Li2CoPO4F.
• Results or Outcomes: The capacity retention of Li2CoPO4F cathode increases from 15% in EC/DMC electrolyte to 51% in F-EPE/DMC electrolyte after 100 cycles at 1 C between 3.0 and 5.4 V.

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