Difluorodiiodomethane

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Difluorodiiodomethane
Names
Preferred IUPAC name
Difluoro(diiodo)methane
Other names
Diiododifluoromethane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.220.511 Edit this at Wikidata
EC Number
  • 692-496-6
  • InChI=1S/CF2I2/c2-1(3,4)5
    Key: SOEBNUZZZSSRNB-UHFFFAOYSA-N
  • C(F)(F)(I)I
Properties
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:[1]
GHS07: Exclamation mark
Warning
H315, H319, H335
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).

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

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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

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

Physical properties

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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

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  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.
  6. ^ 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.
  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.