Chloroiodomethane

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]

Chloroiodomethane
Names
Preferred IUPAC name
Chloro(iodo)methane
Other names
  • Chloroiodomethane
  • Chloroiodomethane
  • Chloromethyl iodide
Identifiers
3D model (JSmol)
1730802
ChemSpider
ECHA InfoCard 100.008.915
EC Number
  • 209-804-8
Properties
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)
8.9 μmol Pa−1 kg−1
1.582
Hazards
GHS pictograms
GHS Signal word Warning
H315, H319, H335
P261, P305+351+338
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Related compounds
Related alkanes
Related compounds
 2-Chloroethanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 chloromethylenating agent Ph3P=CHCl.[1] It reacts with organolithium compounds to give chloromethyllithium (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
  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). doi:10.1080/00268979300101691.


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