Chloroiodomethane

Chloroiodomethane
IUPAC name Chloroiodomethane
Other names Chloro(iodo)methane, Chloromethyl iodide, Chloro-iodo-methane
Identifiers
CAS number	593-71-5
PubChem	11644
ChemSpider	11154 Y
EC number	209-804-8
Jmol-3D images	Image 1 Image 2
SMILES C(Cl)I ClCI
InChI InChI=1S/CH2ClI/c2-1-3/h1H2 Y Key: PJGJQVRXEUVAFT-UHFFFAOYSA-N Y InChI=1/CH2ClI/c2-1-3/h1H2
Properties
Molecular formula	CH2ClI
Molar mass	176.38 g/mol
Appearance	Colorless liquid
Density	2.416 g/cm3 (20 °C) 2.422 g/cm3 (25 °C)
Boiling point	108 - 109 °C
kH	0.89 mol.kg-1.bar-1
Hazards
EU classification	Irritant (Xi)
R-phrases	R36/37/38
S-phrases	S23, S24/25
NFPA 704	1 1 0
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 4, 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. http://cat.inist.fr/?aModele=afficheN&cpsidt=4874194. Retrieved 2007-06-29. 

External links

• Usage in organic synthesis

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