Chloroiodomethane


Chloroiodomethane is the halomethane with the formula is. It is a colorless liquid of use in organic synthesis. Together with other iodomethanes, chloroiodomethane is produced by some microorganisms.

Applications

Chloroiodomethane is used in cyclopropanation, 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. Upon reaction with triphenylphosphine it affords the chloromethylene agent Ph3P=CHCl. It reacts with organolithium compounds to give chloromethyllithium.

Crystallography

It crystallizes orthorhombic crystal system with space group Pnma with lattice constants: a = 6.383, b = 6.706, c = 8.867.