CAS 1339946-60-9, Cat. No EN300-52818608
Reagent for monofluoromethylation
Fluoromethyl trifluoromethanesulfonate (SFM or “magic superfluoromethyl”) is a stable liquid reagent used for monofluoromethylation1. It cleanly reacts with a broad range of nucleophiles, including thiolates, alcohols, carboxylates, and phosphane chalcogenides, giving high yields of fluoromethylated products. It shows unusual reactivity with some heteroaryl carboxylates, sometimes forming rearranged products. SFM is easy to prepare, storable under inert gas, and provides efficient access to –CH₂F building blocks, valuable as bioisosteres in pharmaceutical and chemical biology applications.
Synonyms: fluoromethyl fluorosulfonate; SFM; “magic superfluoromethyl”
Selected publication
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Fluoromethyl Triflate and Fluoromethyl Fluorosulfonate: Easily Accessible and Powerful Fluoromethylation Reagents.
Gisnapp, A.; Trapp, P. C.; Schwabedissen, J.; Stammler, H. G.; Reichel, M.; Leitz, D.; Krumm, B.; Karaghiosoff, K.; Mitzel, N. W. Angewandte Chemie - International Edition 2025, 64 (8). DOI: 10.1002/anie.202420540