Chloroiodomethane is the
halomethane Halomethane compounds are derivatives of methane () with one or more of the hydrogen atoms replaced with halogen atoms ( F, Cl, Br, or I). Halomethanes are both naturally occurring, especially in marine environments, and human-made, most notably ...
with the formula is . It is a colorless liquid of use in
organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
.
Together with other iodomethanes, chloroiodomethane is produced by some microorganisms.
Applications
Chloroiodomethane is used in
cyclopropanation
In organic chemistry, cyclopropanation refers to any chemical process which generates cyclopropane () rings. It is an important process in modern chemistry as many useful compounds bear this motif; for example pyrethroids and a number of quinolo ...
(''Simmon-Smith reaction''), where it often replaces
diiodomethane
Diiodomethane or methylene iodide, commonly abbreviated "MI", is an organoiodine compound. Diiodomethane is a colorless liquid; however, it decomposes upon exposure to light liberating iodine, which colours samples brownish. It is slightly solub ...
because of higher yields and selectivity. It is also used in
Mannich reaction
In organic chemistry, the Mannich reaction is a three-component organic reaction that involves the amino alkylation of an acidic proton next to a carbonyl () functional group by formaldehyde () and a primary or secondary amine () or ammonia (). ...
, aminomethylation,
epoxidation
In organic chemistry, an epoxide is a cyclic ether () with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale for ...
, ring opening and addition to terminal alkenes. It is a precursor to chloromethylenating agent
Ph3P=CHCl.
[ It reacts with organolithium compounds to give chloromethyllithium (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 a r ...
with space group ''Pnma'' with lattice constants
A lattice constant or lattice parameter is one of the physical dimensions and angles that determine the geometry of the unit cells in a crystal lattice, and is proportional to the distance between atoms in the crystal. A simple cubic crystal has ...
: ''a'' = 6.383, ''b'' = 6.706, ''c'' = 8.867 (.10−1 nm).[
]
References
External links
Usage in organic synthesis
Halomethanes
Organochlorides
Organoiodides
{{organohalide-stub