Fluorodiiodomethane

Fluorodiiodomethane

Names
Preferred IUPAC name Fluoro(diiodo)methane
Other names Diiodofluoromethane
Identifiers
CAS Number	1493-01-2  Y
3D model (JSmol)	Interactive image
ChemSpider	9996877
PubChem CID	11822226
UNII	2GD4JG7JL9
CompTox Dashboard (EPA)	DTXSID70473843
InChI InChI=1S/CHFI2/c2-1(3)4/h1H Key: RIHYOLCRHKZJPJ-UHFFFAOYSA-N
SMILES C(F)(I)I
Properties
Chemical formula	CHFI2
Molar mass	285.826 g·mol−1
Density	3.2±0.1 g/cm³
Melting point	259 °C (498 °F; 532 K)
Boiling point	134 °C (273 °F; 407 K)
Hazards
GHS labelling: [1]
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319
Flash point	43.4±5.6 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Fluorodiiodomethane is a trihalomethane with the chemical formula CHFI₂. ^[2]

Synthesis

Fluorodiiodomethane can be obtained by the Finkenstein reaction of dibromofluoromethane with sodium iodide in acetone.

Also, iodoform reacts with mercuric fluoride at 120 °C to afford fluorodiiodomethane after distillation. This reaction is used to prepare large quantities of the reagent. ^{[3] [4]}

Chemical properties

It is a highly efficient precursor of fluorocarbenes. The compound can generate fluorocarbenes that react with alkenes to give compounds containing fluorinated three-membered rings.

It is also a reagent for monofluorocyclopropanation. ^[3]

References

1. "fluoro(diiodo)methane". Sigma Aldrich . Retrieved 28 August 2025.
2. "NCATS Inxight Drugs — Fluorodiiodomethane". drugs.ncats.io. Retrieved 28 August 2025.
3. Navuluri, Chandra Sekhar (2015). "Fluorodiiodomethane". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd: 1–4. doi:10.1002/047084289x.rn01761 . Retrieved 28 August 2025.
4. Hine, Jack; Butterworth, Richard; Langford, Paul B. (1 February 1958). "The Hydrolysis and Deuterium Exchange of Dibromofluoromethane and Fluorodiiodomethane1". Journal of the American Chemical Society . 80 (4): 819–824. doi:10.1021/ja01537a017. ISSN   0002-7863 . Retrieved 28 August 2025.