Chloroiodomethane

Chloroiodomethane is the halomethane with the formula is CH
₂ClI. It is a colorless liquid of use in organic synthesis.^[1] Together with other iodomethanes, chloroiodomethane is produced by some microorganisms.^[2]

Chloroiodomethane

Stereo, skeletal formula of chloroiodomethane with all explicit hydrogens added
Spacefill model of chloroiodomethane
Names
Preferred IUPAC name Chloro(iodo)methane
Other names Chloroiodomethane Chloroiodomethane Chloromethyl iodide
Identifiers
CAS Number	593-71-5 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1730802
ChemSpider	11154 Y
ECHA InfoCard	100.008.915
EC Number	209-804-8
PubChem CID	11644
UNII	X7AF9WG7CX Y
CompTox Dashboard (EPA)	DTXSID50208034
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
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P305+P351+P338
NFPA 704 (fire diamond)	1 1 0
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). Y verify (what is YN ?) Infobox references

Applications

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]

Crystallography

It crystallizes orthorhombic crystal system with space group Pnma with lattice constants: a = 6.383, b = 6.706, c = 8.867 (.10⁻¹ nm).^[4]