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Dichloroiodomethane

Names
IUPAC name dichloro(iodo)methane
Other names DCIM, Chloriodoform (archaic), IDCM, iododichloromethane
Identifiers
CAS Number	594-04-7
3D model (JSmol)	Interactive image
ChemSpider	11165
PubChem CID	11655
UNII	59FJY8K9MX
CompTox Dashboard (EPA)	DTXSID7021570
InChI InChI=1S/CHCl2I/c2-1(3)4/h1HKey: HNLZCOJXSLDGKD-UHFFFAOYSA-N
SMILES ClC(I)Cl
Properties
Chemical formula	CHCl2I
Molar mass	210.82 g·mol
Appearance	pale yellow liquid
Boiling point	131°C
Solubility in water	very slightly
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Dichloroiodomethane (DCIM) is a trihalomethane with the chemical formula CHCl₂I. It is a heavy, nonflammable, transparent pale yellow liquid with a chloroform-like odour. 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. DCIM has an estimated half-life of 275 years in water.

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

Synthesis

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

References

1. ^ Leopold Gmelin, Henry Watts, Chloriodoform in Hand-book of Chemistry (1848), pages 337–339
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

• Sweet-smelling chemicals
• Iodoalkanes
• Chloroalkanes
• Halomethanes