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Fluorine-18-Labeled Diethylaminosulfur Trifluoride (DAST): An F-for-OH Fluorinating Agent

Mallinckrodt Institute of Radiology, Washington University School of Medicine, St. Louis, Missouri

Correspondence: For reprints contact: Maria G. Straatmann, Mallinckrodt Institute of Radiology, Washington University School of Medicine, 510 S. Kingshighway Blvd., St. Louis, MO 63110.

ABSTRACT

A new fluorinating agent was developed by incorporation of ¹⁸F into diethylaminosulfur trifluoride (DAST), a reagent capable of replacing hydroxyl and carbonyl oxygen with fluorine. The DAST was synthesized using sulfur tetrafluoride and trimethylsilyldiethylamine in a freon-11 solvent at –78°C and purified by reduced-pressure distillation. Labeling was then accomplished by exchange with anhydrous ¹⁸F-hydrofluoric acid, which caused more than 80% of the available activity to be incorporated into the DAST. Fluorine-18-labeled methyl fluoride, ethyl fluoride, and 2-fluoroethanol were prepared from methanol, ethanol, and ethylene glycol, with yields of 20%, 25%, and 12%, respectively.