Chloroiodomethane

[2] Chloroiodomethane is used in cyclopropanation (Simmon-Smith reaction), 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.

It is a precursor to agent Ph3P=CHCl that can add a chloromethylene group (=CHCl).

[1] It reacts with organolithium compounds to give chloromethyl lithium (ClCH2Li).

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

Stereo, skeletal formula of chloroiodomethane with all explicit hydrogens added
Stereo, skeletal formula of chloroiodomethane with all explicit hydrogens added
Spacefill model of chloroiodomethane
Spacefill model of chloroiodomethane
NFPA 704 four-colored diamond Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazards (white): no code