Dichloroiodomethane

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/h1H Key: HNLZCOJXSLDGKD-UHFFFAOYSA-N;
	SMILES ClC(I)Cl;
Properties
Chemical formula	CHCl2I
Molar mass	210.82 g·mol−1
Appearance	pale yellow liquid
Boiling point	131°C
Solubility in water	very slighlty
	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.^[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

^ ^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

Zdroj:https://en.wikipedia.org?pojem=Dichloroiodomethane
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[handbook-1] Leopold Gmelin, Henry Watts, Chloriodoform in Hand-book of Chemistry (1848), pages 337–339

[d213-2] 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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v t e Halomethanes
Unsubstituted	CH₄
Monosubstituted	CH₃F CH₃Cl CH₃Br CH₃I CH₃At
Disubstituted	CH₂F₂ CH₂ClF CH₂BrF CH₂FI CH₂Cl₂ CH₂BrCl CH₂ClI CH₂Br₂ CH₂BrI CH₂I₂
Trisubstituted	CHF₃ CHClF₂ CHBrF₂ CHF₂I CHCl₂F CHBrClF CHClFI CHBr₂F CHBrFI CHFI₂ CHCl₃ CHBrCl₂ CHCl₂I CHBr₂Cl CHBrClI CHClI₂ CHBr₃ CHBr₂I CHBrI₂ CHI₃
Tetrasubstituted	CF₄ CClF₃ CBrF₃ CF₃I CCl₂F₂ CBrClF₂ CClF₂I CBr₂F₂ CBrF₂I CF₂I₂ CCl₃F CBrCl₂F CCl₂FI CBr₂ClF C*BrClFI CClFI₂ CBr₃F CBr₂FI CBrFI₂ CFI₃ CCl₄ CBrCl₃ CCl₃I CBr₂Cl₂ CBrCl₂I CCl₂I₂ CBr₃Cl CBr₂ClI CBrClI₂ CClI₃ CBr₄ CBr₃I CBr₂I₂ CBrI₃ CI₄
* Chiral compound.