Difluoroiodomethane

(Difluoroiodomethane) [1493-03-4] CHF2I (MW 177.92) InChI = 1S/CHF2I/c2-1(3)4/h1H InChIKey = YSLFMGDEEXOKHF-UHFFFAOYSA-N (generally used as a precursor of CF2 carbene, CHF2− anion, or CHF2√ radical) Alternative Name: difluoromethyl iodide. Physical Data: clear colorless liquid; bp = 21–23 °C1; mp =−122 °C2. Solubility: soluble in most organic solvents. Form Supplied in: liquid, in cylinder with valve (Oakwood). Usually prepared in the laboratory due to low availability and high cost. Analysis of Reagent Purity: 1H NMR (d6-acetone):3δ 8.16 (t, J = 56.2 Hz); 19F NMR (CFCl3):1δ−68 (d, J = 56 Hz). Handling, Storage, and Precautions:4 use caution when handling. Irritating to skin, eyes, and respiratory system. Avoid prolonged exposure. Keep container tightly closed in a dry environment. Recommended storage temperature: −20 °C. Preparative Methods: the reagent is prepared via the Finkelstein reaction of iodoform with fluorides of silver or mercury2, 5, 6; via the Hunsdiecker reaction of silver or mercury difluoroacetates in the presence of iodine7, 8; or via the trapping of in situ generated difluorocarbene with iodide anion and a proton source.1, 3, 9 Purification: trap-to-trap distillation.1