Difluorodiiodomethane

Difluorodiiodomethane
Names
	Preferred IUPAC name Difluoro(diiodo)methane
	Other names Diiododifluoromethane
Identifiers
CAS Number	1184-76-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	2018740;
ECHA InfoCard	100.220.511
EC Number	692-496-6;
PubChem CID	2737095;
CompTox Dashboard (EPA)	DTXSID00371828;
	InChI InChI=1S/CF2I2/c2-1(3,4)5 Key: SOEBNUZZZSSRNB-UHFFFAOYSA-N;
	SMILES C(F)(F)(I)I;
Properties
Chemical formula	CF2I2
Molar mass	303.817 g·mol−1
Appearance	pale yellow liquid
Density	3.2 g/cm³
Boiling point	89.4 °C (192.9 °F; 362.5 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P271, P280
Flash point	24.3 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Difluorodiiodomethane is a tetrahalomethane with the chemical formula CF₂I₂.^[2] This is a halomethane containing two fluorine atoms and two iodine atoms attached to the methane backbone.^[3]^[4]

Synthesis

It can be prepared by reacting potassium difluorobromoacetate or methyl difluorobromoacetate with cuprous iodide, potassium iodide, and iodine in the DMF solution, or by reacting tetraiodomethane, 1,2-dichlorobenzene, and mercury fluoride.^[5]^[6]

CBrF₂CO₂K + KI + CuI + I₂ → CF₂I₂ + KBr + CO₂

Chemical properties

In the presence of lead tetraacetate, it reacts with vinyltrimethylsilane to form (3,3-difluoro-1,3-diiodopropyl)trimethylsilane.^[7]

Physical properties

The compound forms pale yellow liquid that decomposes slowly at room temperature and upon exposure to light, turning burgundy due to the liberation of iodine.^[6]

References

^ "Difluorodiiodomethane". Sigma Aldrich. Retrieved 3 September 2025.
^ Neckers, Douglas C.; Volman, David H.; Bünau, Günther von (24 September 2009). Advances in Photochemistry, Volume 22. John Wiley & Sons. ISBN 978-0-470-13380-4. Retrieved 3 September 2025.
^ Luo, Yu-Ran (9 March 2007). Comprehensive Handbook of Chemical Bond Energies. CRC Press. p. 244. ISBN 978-1-4200-0728-2. Retrieved 3 September 2025.
^ Kuchitsu, Kozo (9 March 2013). Structure of Free Polyatomic Molecules: Basic Data. Springer Science & Business Media. p. 83. ISBN 978-3-642-45748-7. Retrieved 3 September 2025.
^ Katritzky, Alan R.; Gilchrist, Thomas L.; Meth-Cohn, Otto; Rees, Charles Wayne (21 March 2003). Comprehensive Organic Functional Group Transformations. Elsevier. p. 227. ISBN 978-0-08-042704-1. Retrieved 3 September 2025.
^ ^a ^b Navuluri, Chandra Sekhar (2015). "Difluorodiiodomethane". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd: 1–4. doi:10.1002/047084289x.rn01760. ISBN 978-0-470-84289-8. Retrieved 3 September 2025.
^ Li, An-Rong; Chen, Qing-Yun (December 1997). "Lead Tetraacetate Induced Addition Reaction of Difluorodiiodomethane to Alkenes and Alkynes. Synthesis of Fluorinated Telechelic Compounds". Synthesis. 1997 (12): 1481–1488. doi:10.1055/s-1997-1378. ISSN 0039-7881. Retrieved 3 September 2025.

[1] "Difluorodiiodomethane". Sigma Aldrich. Retrieved 3 September 2025.

[2] Neckers, Douglas C.; Volman, David H.; Bünau, Günther von (24 September 2009). Advances in Photochemistry, Volume 22. John Wiley & Sons. ISBN 978-0-470-13380-4. Retrieved 3 September 2025.

[3] Luo, Yu-Ran (9 March 2007). Comprehensive Handbook of Chemical Bond Energies. CRC Press. p. 244. ISBN 978-1-4200-0728-2. Retrieved 3 September 2025.

[4] Kuchitsu, Kozo (9 March 2013). Structure of Free Polyatomic Molecules: Basic Data. Springer Science & Business Media. p. 83. ISBN 978-3-642-45748-7. Retrieved 3 September 2025.

[5] Katritzky, Alan R.; Gilchrist, Thomas L.; Meth-Cohn, Otto; Rees, Charles Wayne (21 March 2003). Comprehensive Organic Functional Group Transformations. Elsevier. p. 227. ISBN 978-0-08-042704-1. Retrieved 3 September 2025.

[Nav-6] Navuluri, Chandra Sekhar (2015). "Difluorodiiodomethane". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd: 1–4. doi:10.1002/047084289x.rn01760. ISBN 978-0-470-84289-8. Retrieved 3 September 2025.

[7] Li, An-Rong; Chen, Qing-Yun (December 1997). "Lead Tetraacetate Induced Addition Reaction of Difluorodiiodomethane to Alkenes and Alkynes. Synthesis of Fluorinated Telechelic Compounds". Synthesis. 1997 (12): 1481–1488. doi:10.1055/s-1997-1378. ISSN 0039-7881. Retrieved 3 September 2025.

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