Fluorodiiodomethane

Fluorodiiodomethane
Names
	Preferred IUPAC name Fluoro(diiodo)methane
	Other names Diiodofluoromethane
Identifiers
CAS Number	1493-01-2 ;
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:
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

^ "fluoro(diiodo)methane". Sigma Aldrich. Retrieved 28 August 2025.
^ "NCATS Inxight Drugs — Fluorodiiodomethane". drugs.ncats.io. Retrieved 28 August 2025.
^ ^a ^b Navuluri, Chandra Sekhar (2015). "Fluorodiiodomethane". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd: 1–4. doi:10.1002/047084289x.rn01761. ISBN 978-0-470-84289-8. Retrieved 28 August 2025.
^ 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. Bibcode:1958JAChS..80..819H. doi:10.1021/ja01537a017. ISSN 0002-7863. Retrieved 28 August 2025.

[1] "fluoro(diiodo)methane". Sigma Aldrich. Retrieved 28 August 2025.

[2] "NCATS Inxight Drugs — Fluorodiiodomethane". drugs.ncats.io. Retrieved 28 August 2025.

[Nav-3] Navuluri, Chandra Sekhar (2015). "Fluorodiiodomethane". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd: 1–4. doi:10.1002/047084289x.rn01761. ISBN 978-0-470-84289-8. 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. Bibcode:1958JAChS..80..819H. doi:10.1021/ja01537a017. ISSN 0002-7863. Retrieved 28 August 2025.

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