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Trimethyloxonium tetrafluoroborate

Trimethyloxonium tetrafluoroborate is the organic compound with the formula [(CH3)3O]+[BF4]−. This salt is a strong methylating agent, being a synthetic equivalent of CH+3. It is a white solid that rapidly decomposes upon exposure to atmospheric moisture, although it is robust enough to be weighed quickly without inert atmosphere protection. Triethyloxonium tetrafluoroborate is a closely related compound.

Preparation and reactions
The compound is prepared by the reaction of boron trifluoride with dimethyl ether and epichlorohydrin: being stronger than methyl sulfonate esters, including methyl triflate and methyl fluorosulfonate ("magic methyl"). Only the exotic dimethylhalonium reagents (, X = Cl, Br, I), methyl carboranate reagents, and the transiently generated methyldiazonium cation () are stronger sources of electrophilic methyl groups. This compound is rapidly destroyed by atmospheric moisture and is best stored in an argon atmosphere at −20 °C. The degradation products of this reagent are corrosive, although are considerably less hazardous than methyl triflate or methyl fluorosulfonate, as they do not evaporate. Trimethyloxonium tetrafluoroborate is useful for the methyl esterification of carboxylic acids under conditions where acid-catalyzed reactions cannot be used:{{cite journal : ==References==
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