Dichlorodiiodomethane

Dichlorodiiodomethane

Names
Preferred IUPAC name Dichloro(diiodo)methane
Identifiers
CAS Number	594-23-0  Y
3D model (JSmol)	Interactive image
ChemSpider	15218897
PubChem CID	12542273
CompTox Dashboard (EPA)	DTXSID10501896
InChI InChI=1S/CCl2I2/c2-1(3,4)5 Key: ZOWYTDVMTPRWGU-UHFFFAOYSA-N
SMILES ClC(Cl)(I)I
Properties
Chemical formula	CCl2I2
Molar mass	336.72 g·mol−1
Appearance	unstable solid
Density	3.2 g/cm³
Melting point	85 °C (185 °F; 358 K)
Boiling point	206.8 °C (404.2 °F; 479.9 K)
Hazards
Flash point	78.9 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Dichlorodiiodomethane is a tetrahalomethane with the chemical formula CCl₂I₂. ^[1] This complex organic compound is characterized by having four halogen atoms—two chlorine and two iodine—attached to a methane backbone. ^[2]

Synthesis

The compound was initially prepared by Höland in 1887 by treating CH₂Cl₂ with Br₂/I₂ at 100-200 °C for several weeks. Distillation gave dichloroiodomethane and dichlorodiiodomethane. ^[3]

Physical properties

The compound forms an unstable solid that melts and decomposes at 85 °C. Its heat of formation (−ΔH°F, 25 °C, gas phase) is −24 kcal·mol⁻¹ (compare to 70 kcal·mol⁻¹ for difluorodiiodomethane and −43 kcal·mol⁻¹ for dibromodiiodomethane, calculated values). Its carbon-13 shift is −90.7 ppm. ^[4]

References

1. "dichlorodiiodomethane". NIST . Retrieved 31 August 2025.
2. "Dichlorodiiodomethane | Chemical Substance Information | J-GLOBAL". jglobal.jst.go.jp. Retrieved 31 August 2025.
3. 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 31 August 2025.
4. Somayajulu, Gollakota R; Kennedy, John R; Vickrey, Thomas M; Zwolinski, Bruno J (1 March 1979). "Carbon-13 chemical shifts for 70 halomethanes". Journal of Magnetic Resonance (1969). 33 (3): 559–568. Bibcode:1979JMagR..33..559S. doi:10.1016/0022-2364(79)90167-7. ISSN   0022-2364 . Retrieved 31 August 2025.