Organofluorine

Organofluorine refers to organic compounds that contain at least one covalent carbon–fluorine bond. The carbon–fluorine bond is among the strongest single bonds in organic chemistry, giving organofluorines high thermal and chemical stability and often significant metabolic resistance. Fluorine’s high electronegativity also strongly affects molecular properties such as reactivity, lipophilicity, acidity, and pKa, enabling applications in pharmaceuticals, agrochemicals, and materials.

Most organofluorines are synthetic; natural occurrences are rare but include fluoroacetate-containing toxins found in some plants and microorganisms. Synthesis relies on introducing C–F bonds via electrophilic fluorination (for example, reagents such as Selectfluor or NFSI) or nucleophilic fluorination (fluoride sources with activating substrates, including DAST or Deoxo-Fluor). Fluorination can target alkanes, alkenes, arenes, and carbonyl derivatives, and late-stage fluorination is widely used in drug development. Polyfluorinated and perfluorinated compounds arise from polymerization or multi-step fluorination and include materials such as polytetrafluoroethylene.

Applications of organofluorines span medicine, agriculture, and materials science. Fluorinated motifs are common in pharmaceuticals, where fluorine can enhance metabolic stability and bioavailability. In agrochemicals, fluorinated compounds improve potency and persistence. Fluorinated polymers impart chemical resistance and low surface energy, while fluorinated solvents and refrigerants offer stability under demanding conditions. Safety and environment: many organofluorines are persistent or potentially toxic in the environment, particularly per- and polyfluorinated substances. Regulatory oversight focuses on emissions, persistence, and bioaccumulation, and responsible handling remains essential.