Chloroiodomethane is the
halomethane
Halomethane compounds are derivatives of methane () with one or more of the hydrogen atoms replaced with halogen atoms (Fluorine, F, Chlorine, Cl, Bromine, Br, or Iodine, I). Halomethanes are both naturally occurring, especially in marine environm ...
with the formula is . It is a colorless liquid of use in
organic synthesis
Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...
.
Together with other iodomethanes, chloroiodomethane is produced by some microorganisms.
Applications
Chloroiodomethane is used in
cyclopropanation (''Simmon-Smith reaction''), where it often replaces
diiodomethane
Diiodomethane or methylene iodide, commonly abbreviated "MI", is an organoiodine compound. Diiodomethane is a very dense colorless liquid; however, it decomposes upon exposure to light liberating iodine, which colours samples brownish. It is slig ...
because of higher yields and selectivity. It is also used in
Mannich reaction, aminomethylation,
epoxidation
In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ...
, ring opening and addition to terminal alkenes. It is a precursor to agent
Ph3P=CHCl that can add a
chloromethylene group (=CHCl).
[ It reacts with organolithium compounds to give chloromethyl lithium (ClCH2Li).
]
Crystallography
It crystallizes orthorhombic crystal system
In crystallography, the orthorhombic crystal system is one of the 7 crystal systems. Orthorhombic lattices result from stretching a cubic lattice along two of its orthogonal pairs by two different factors, resulting in a rectangular prism with ...
with space group ''Pnma'' with lattice constants: ''a'' = 6.383, ''b'' = 6.706, ''c'' = 8.867 (.10−1 nm).[
]
References
External links
Usage in organic synthesis
Halomethanes
Chloroiodoalkanes
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