Dichloroiodomethane

Dichloroiodomethane
Names
IUPAC name
dichloro(iodo)methane
Other names
DCIM, Chloriodoform (archaic),[1] IDCM, iododichloromethane
Identifiers
3D model (JSmol)
ChemSpider
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
Appearance pale 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. ^ a b c d Leopold Gmelin, Henry Watts, Chloriodoform in Hand-book of Chemistry (1848), pages 337–339
  2. ^ a b 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