Chloroiodomethane

Chloroiodomethane
Names
Preferred IUPAC name
Chloro(iodo)methane
Other names
  • Chloroiodomethane
  • Chloro-iodo-methane
  • 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
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 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 chemical formula is CH
2ClI.[1] 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).[2]

Applications

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. Also, chloroiodomethane is used as an intermediate substance in pharmaceuticals, organic synthesis, agrochemicals, and dyestuff.[3]

References

  1. ↑ "Chloroiodomethane". Sigma Aldrich. sigmaaldrich.com. Retrieved 7 June 2017.
  2. ↑ 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.
  3. ↑ "Chloroiodomethane, 98%, stab. with copper". alfa.com. Retrieved 7 June 2017.


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