Chloroiodomethane

Chloroiodomethane
Names
Preferred IUPAC name
Chloro(iodo)methane
Other names
  • Chloroiodomethane
  • Chloro-iodo-methane
  • Chloromethyl iodide
Identifiers
593-71-5 YesY
3D model (Jmol) Interactive image
1730802
ChemSpider 11154 YesY
ECHA InfoCard 100.008.915
EC Number 209-804-8
PubChem 11644
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
Xi
R-phrases R36/37/38
S-phrases S26, S36
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
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

Chloroiodomethane is a mixed liquid halomethane very soluble in acetone, benzene, diethyl ether and alcohol. Its refractive index is 1.5812 - 1.5832.

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

Chloroiodomethane is used in cyclopropanation (Simmon-Smith reaction), Mannich reaction, aminomethylation, epoxidation, ring opening and addition to terminal alkenes. It often replaces diiodomethane because of higher yields and selectivity.

References

  1. ↑ 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. Retrieved 2007-06-29.


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