Chloroiodomethane

Chloroiodomethane
	Stereo, skeletal formula of chloroiodomethane with all explicit hydrogens added
	Spacefill model of chloroiodomethane
Names
	Preferred IUPAC name Chloro(iodo)methane
	Other names Chloroiodomethane; Chloroiodomethane; Chloromethyl iodide;
Identifiers
CAS Number	593-71-5 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1730802
ChemSpider	11154 ;
ECHA InfoCard	100.008.915
EC Number	209-804-8;
PubChem CID	11644;
UNII	X7AF9WG7CX ;
CompTox Dashboard (EPA)	DTXSID50208034 ;
	InChI InChI=1S/CH2ClI/c2-1-3/h1H2 Key: PJGJQVRXEUVAFT-UHFFFAOYSA-N ;
	SMILES ClCI;
Properties
Chemical formula	CH2ClI
Molar mass	176.38 g·mol−1
Appearance	Colorless liquid
Density	2.422 g mL−1
Boiling point	108 to 109 °C (226 to 228 °F; 381 to 382 K)
Henry's law; constant (kH)	8.9 μmol Pa−1 kg−1
Refractive index (nD)	1.582
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P305+P351+P338
NFPA 704 (fire diamond)	1 1 0
Related compounds
Related alkanes	Chloromethane; Bromochloromethane; Dibromochloromethane;
Related compounds	2-Chloroethanol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Chloroiodomethane is the halomethane with the formula is CH
₂ClI. It is a colorless liquid of use in organic synthesis.^[1] Together with other iodomethanes, chloroiodomethane is produced by some microorganisms.^[2]

Applications

Chloroiodomethane is used in cyclopropanation (Simmon-Smith reaction), where it often replaces diiodomethane because of higher yields and selectivity. It is also used in Mannich reaction, aminomethylation, epoxidation, ring opening and addition to terminal alkenes. It is a precursor to agent Ph₃P=CHCl that can add a chloromethylene group (=CHCl).^[1] It reacts with organolithium compounds to give chloromethyl lithium (ClCH₂Li).^[3]

Crystallography

It crystallizes orthorhombic crystal system with space group Pnma with lattice constants: a = 6.383, b = 6.706, c = 8.867 (.10⁻¹ nm).^[4]

References

^ ^a ^b Miyano, Sotaro; Friestad, Gregory K. (2008). "Chloroiodomethane". E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc110.pub2. ISBN 978-0471936237.
^ Fuse, Hiroyuki; Inoue, Hiroyuki; Murakami, Katsuji; Takimura, Osamu; Yamaoka, Yukiho (2003). "Production of free and organic iodine by Roseovarius spp.". FEMS Microbiology Letters. 229 (2): 189–94. doi:10.1016/S0378-1097(03)00839-5. PMID 14680698.
^ Donald S. Matteson (2001). "Chloromethyllithium". EEROS. doi:10.1002/047084289X.rc117. ISBN 0471936235.
^ Torrie B. H.; Binbrek O. S.; von Dreele R. (1993). "Crystal structure of chloroiodomethane". Mol. Phys. 79 (4): 869–874(6). Bibcode:1993MolPh..79..869T. doi:10.1080/00268979300101691.

External links

Usage in organic synthesis

This article about an organic halide is a stub. You can help Wikipedia by expanding it.

[eEROS-1] Miyano, Sotaro; Friestad, Gregory K. (2008). "Chloroiodomethane". E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc110.pub2. ISBN 978-0471936237.

[2] Fuse, Hiroyuki; Inoue, Hiroyuki; Murakami, Katsuji; Takimura, Osamu; Yamaoka, Yukiho (2003). "Production of free and organic iodine by Roseovarius spp.". FEMS Microbiology Letters. 229 (2): 189–94. doi:10.1016/S0378-1097(03)00839-5. PMID 14680698.

[3] Donald S. Matteson (2001). "Chloromethyllithium". EEROS. doi:10.1002/047084289X.rc117. ISBN 0471936235.

[4] Torrie B. H.; Binbrek O. S.; von Dreele R. (1993). "Crystal structure of chloroiodomethane". Mol. Phys. 79 (4): 869–874(6). Bibcode:1993MolPh..79..869T. doi:10.1080/00268979300101691.

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Chloroiodomethane

Applications

Crystallography

References

External links

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