Chloroiodomethane

Chloroiodomethane

Stereo, skeletal formula of chloroiodomethane with all explicit hydrogens added
Names
Preferred IUPAC name Chloroiodomethane
Systematic IUPAC name Chloro(iodo)methane
Other names Chloro-iodo-methane Chloromethyl iodide
Identifiers
CAS Number	593-71-5 Y
Beilstein Reference	1730802
ChemSpider	11154 Y
EC Number	209-804-8
Jmol 3D model	Interactive image
PubChem	11644
InChI InChI=1S/CH2ClI/c2-1-3/h1H2 Y Key: PJGJQVRXEUVAFT-UHFFFAOYSA-N Y
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
Vapor pressure	{{{value}}}
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).
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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).

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.

External links

• Usage in organic synthesis