Dichloroiodomethane

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Dichloroiodomethane
Dichloroiodomethane.png
Names
IUPAC name
dichloro(iodo)methane
Other names
DCIM, Chloriodoform (archaic), [1] IDCM, iododichloromethane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/CHCl2I/c2-1(3)4/h1H
    Key: HNLZCOJXSLDGKD-UHFFFAOYSA-N
  • ClC(I)Cl
Properties
CHCl2I
Molar mass 210.82 g·mol−1
Appearancepale yellow liquid
Boiling point 131°C [2]
very slightly
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dichloroiodomethane (DCIM) is a trihalomethane with the chemical formula CHCl2I. It is a heavy, nonflammable, transparent pale yellow liquid with a chloroform-like odour. [1] DCIM is soluble in organic solvents like acetone, diethyl ether, ethanol and benzene. [2] It decomposes in contact with air and light. It has been detected in disinfected tap water and is considered to be a contaminant. [3] DCIM has an estimated half-life of 275 years in water. [4]

It was discovered by Georges-Simon Serullas in 1824, two years after his discovery of iodoform. [1]

Synthesis

Many synthesis routes are known. Reaction of chloroform with sodium iodide [5] or iodoethane [6] gives dichloroiodomethane. Older methods include distillation of iodoform with phosphorus pentachloride or mercuric chloride. [1]

References

  1. 1 2 3 4 Leopold Gmelin, Henry Watts, Chloriodoform in Hand-book of Chemistry (1848), pages 337–339
  2. 1 2 D213 Dichloroiodomethane, The Dictionary of substances and their effects, p. 324
  3. ↑ Emma Goslan, Kenneth Clive Thompson, Simon Gillespie, Disinfection By-products in Drinking Water (2015), Royal Society of Chemistry
  4. ↑ Liu, David H. F; Liptak, Bela G, Groundwater and surface water pollution, page 57
  5. ↑ Determination of Dichloroiodomethane in Water (1996)
  6. ↑ Nariyoshi Kawabata, Masami Tanimoto, Shigehiro Fujiwara. Synthesis of monohalocyclopropane derivatives from olefins by the reaction with trihalomethanes and copper, Tetrahedron, 1979
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