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]
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| Names | |
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| IUPAC name
dichloro(iodo)methane
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| Other names
DCIM, Chloriodoform (archaic),[1] IDCM, iododichloromethane
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| 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).
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It was discovered by Georges-Simon Serullas in 1824, two years after his discovery of iodoform.[1]
Synthesis
editMany 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
edit- ^ a b c d Leopold Gmelin, Henry Watts, Chloriodoform in Hand-book of Chemistry (1848), pages 337–339
- ^ a b D213 Dichloroiodomethane, The Dictionary of substances and their effects, p. 324
- ^ Emma Goslan, Kenneth Clive Thompson, Simon Gillespie, Disinfection By-products in Drinking Water (2015), Royal Society of Chemistry
- ^ Liu, David H. F; Liptak, Bela G, Groundwater and surface water pollution, page 57
- ^ Determination of Dichloroiodomethane in Water (1996)
- ^ Nariyoshi Kawabata, Masami Tanimoto, Shigehiro Fujiwara. Synthesis of monohalocyclopropane derivatives from olefins by the reaction with trihalomethanes and copper, Tetrahedron, 1979