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Synthesis and application of fluoroiodomethane

Synthesis and application of Fluoroiodomethane 373-53-5,Handling, Storage, and Precautions: fluoroiodomethane is toxic by inhalation, in contact with skin, and if swallowed. It should be used only in a chemical fume hood. Fluoroiodomethane is stable under normal conditions, but is incompatible with strong oxidizing agents.


Grégory Landelle & Jean-François Paquin
Université Laval, Québec, Québec, Canada

Handling, Storage, and Precautions: fluoroiodomethane is toxic
by inhalation, in contact with skin, and if swallowed. It should
be used only in a chemical fume hood. Fluoroiodomethane is
stable under normal conditions, but is incompatible with strong
oxidizing agents.

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Alternate Name: fluoromethyliodide.Physical Data: bp 53–54 ◦C.Solubility: sol in most organic solvents.Form Supplied in: colorless liquid; few commercial sources.Purification: distilled at 760 mmHg.

Preparation. As fluoroiodomethane is scarcely commerciallyavailable, it can be prepared in moderate yield according to Bur-on and Greenlimb’s procedure by reacting diiodomethane withmercury(II) fluoride (eq 1).1 18F-Labeled fluoroiodomethane hasbeen obtained, in moderate yield, by a nucleophilic substitutioneaction of diiodomethane with [18F] KF under mild conditionseq 2).2

Fluoromethylation. Fluoroiodomethane can react with var-ious nucleophiles (phenols, benzoic acid derivatives, amines,amides, and thiol derivatives) to give the corresponding
fluoromethylated products (eq 3).2,3 However, reproducibilityproblems have been observed since some of the fluoromethylatedproducts are unstable.4,5Preparation of Fluorophosphonium Salts En Route toTerminal Fluoroalkenes. Fluoroiodomethane reacts with triph

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