Trifluoroiodomethane

[2314-97-8] CF3I (MW 195.91) InChI = 1S/CF3I/c2-1(3,4)5 InChIKey = VPAYJEUHKVESSD-UHFFFAOYSA-N (trifluoromethylating reagent) Alternate Name: trifluoromethyl iodide. Physical Data: bp −22 °C.1 Solubility: sol ether, acetone, alcohol, benzene. Form Supplied in: gas; commercially available. Preparative Methods: prepared by the fluorination of CI4 with IF5 (eq 1),2 or by the Hunsdiecker reaction of Silver(I) Trifluoroacetate with an excess of Iodine (eq 2),3 or by the reaction of trifluoroacetyl fluoride with Lithium Iodide (eq 3).4 More recently, Chen reported a convenient method for the synthesis of CF3I by the reaction of XCF2CO2Me (X = Br, Cl) with iodine, KF, and CuI (eq 4).5 (1) (2) (3) (4) CF3I can be prepared by electrophilic fluorination of sodium iodide with (trifluoromethyl)dibenzothiotriflate, a process that can be accelerated by light (eq 5).21 Reaction of CF3Br with elemental zinc in DMF led to the formation of trifluoromethylzinc bromide that reacted with ICl to afford the desired CF3I (eq 6).22 This is a less damaging reaction pathway than the decarboxylation route using silver or mercury trifluoroacetates. (5) (6) More recently, the preparation from pentafluoroethane was reported by its reaction with iodine in the presence of catalytic amounts of alkali metals (eq 7).23 (7) A novel vapor-phase process for the production of CF3I was successfully developed by means of the reaction of CHF3 with I2 in the presence of alkali metal salts supported on an activated carbon carrier as catalysts (eq 8).24 (8)