G. Prakash, Fang Wang
Sep 15, 2011
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Abstract
[421-50-1] C3H3F3O (MW 112.05) InChI = 1S/C3H3F3O/c1-2(7)3(4,5)6/h1H3 InChIKey = FHUDAMLDXFJHJE-UHFFFAOYSA-N (1,1,1-trifluoroisopropanol precursor; precursor of methyl(trifluoromethyl)dioxirane for the oxidations of various organic compounds; a valuable trifluoromethyl-containing building block for the syntheses of various fluoroorganics) Alternate Names: α,α,α-trifluoroacetone; 1,1,1-trifluoro-2-propanone; methyl trifluoromethyl ketone. Physical Data: bp 21.5–22.5 °C; d20 1.282 g mL−1. Solubility: sol in water, ether, CHCl3, and other organic solvents. Form Supplied in: colorless liquid; commercially available. Purification: by distillation. Preparative Methods: can be prepared by several synthetic routes. The compound was first prepared through the decarboxylation of ethyl 4,4,4-trifluoro-3-oxobutanoate (CF3COCH2CO2Et).1 It was reported that α,α,α-trifluoroacetone (CF3COCH3) can be obtained in 56% yield by treating trifluoroacetic acid (CF3CO2H) with an excess amount of methylmagnesium iodide (MeMgI, 3 equiv).2 Utilizing the Ruppert–Prakash reagent (TMSCF3),3 alternatively, CF3COCH3 was obtained in 86% yield through the reaction between TMSCF3 and ethyl acetate in the presence of cesium fluoride (CsF).4 In addition to the above-mentioned approaches, CF3COCH3 was also obtained in a moderate yield via a Cu(I)-catalyzed reaction between sodium trifluoroacetate (CF3CO2Na) and acetyl chloride (CH3COCl).5 Handling, Storage, and Precautions: avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Use explosion-proof equipment and keep away from sources of ignition. Keep container tightly sealed in a dry and well-ventilated fume hood. Recommended to store at 2–8 °C. Pressure may accumulate over time causing containers to burst.