Dichloroiodomethane Explained

Dichloroiodomethane (DCIM) is a trihalomethane with the chemical formula . 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. It decomposes in contact with air and light. It has been detected in disinfected tap water and is considered to be a contaminant.[2] DCIM has an estimated half-life of 275 years in water.[3]

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[4] or iodoethane[5] gives dichloroiodomethane. Older methods include distillation of iodoform with phosphorus pentachloride or mercuric chloride.[1]

Notes and References

  1. Leopold Gmelin, Henry Watts, Chloriodoform in Hand-book of Chemistry (1848), pages 337–339
  2. Emma Goslan, Kenneth Clive Thompson, Simon Gillespie, Disinfection By-products in Drinking Water (2015), Royal Society of Chemistry
  3. Liu, David H. F; Liptak, Bela G, Groundwater and surface water pollution, page 57
  4. https://archive.org/details/LABORATORYSERVIC00CLEM07675.ome/page/n24/mode/1up Determination of Dichloroiodomethane in Water (1996)
  5. Nariyoshi Kawabata, Masami Tanimoto, Shigehiro Fujiwara. Synthesis of monohalocyclopropane derivatives from olefins by the reaction with trihalomethanes and copper, Tetrahedron, 1979