Bis(2,2,2-tifluoroethyl) malonate

CAS 104883-33-2, Cat. No EN300-51848569
Reagent activated acyl donor

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Bis(2,2,2-trifluoroethyl) malonate is a fluorinated malonate ester that serves as a nucleophile and an activated acyl donor in organic synthesis^1,2. It features enhanced acidity (pKa 9.7) compared to standard dialkyl malonates, enabling selective alkylation reactions. This reagent undergoes Mitsunobu-type alkylation with a broad range of alcohols, including carbohydrates, leading to mono- and dialkylated products. It participates in palladium-catalyzed bisdienylation, facilitating regio- and stereoselective C–C bond formation with dienyl alcohols. Additionally, it acts as an acyl donor in enzymatic acylation, allowing regioselective functionalization of multifunctional molecules. This colorless liquid is insoluble in water but dissolves well in organic solvents and remains stable under ambient conditions.

Synonyms: bis(2,2,2-trifluoroethyl) malonate; propanedioic acid, bis(2,2,2-trifluoroethyl) ester; 1,3-bis(2,2,2-trifluoroethyl) propanedioate