Iodobenzene dichloride
Encyclopedia
Iodobenzene dichloride (PhICl2) is a complex of iodobenzene
with chlorine
. It is used as an oxidant.
Single-crystal X-ray crystallography has been used to determine its structure; as can be predicted by VSEPR theory
, it adopts a T-shaped geometry about the central iodine atom.
in chloroform
, from which it precipitates. The same reaction has been reported at pilot plant scale (20 kg) as well.
An alternate preparation involving the use of chlorine
generated in situ by the action of sodium hypochlorite on hydrochloric acid
has also been described.
(PhIO), and is oxidized by sodium hypochlorite to give iodoxybenzene (PhIO2).
In organic synthesis
, iodobenzene dichloride is used as a reagent for the selective chlorination of alkene
s and alkyne
s.
Iodobenzene
Iodobenzene is an organic compound consisting of a benzene ring substitituted with one iodine atom. It is useful as a synthetic intermediate in organic chemistry.-Preparation:...
with chlorine
Chlorine
Chlorine is the chemical element with atomic number 17 and symbol Cl. It is the second lightest halogen, found in the periodic table in group 17. The element forms diatomic molecules under standard conditions, called dichlorine...
. It is used as an oxidant.
Single-crystal X-ray crystallography has been used to determine its structure; as can be predicted by VSEPR theory
VSEPR theory
Valence shell electron pair repulsion theory is a model in chemistry used to predict the shape of individual molecules based upon the extent of electron-pair electrostatic repulsion. It is also named Gillespie–Nyholm theory after its two main developers...
, it adopts a T-shaped geometry about the central iodine atom.
Preparation
Iodobenzene dichloride is not stable, and is not commonly available commercially. It is prepared by passing chlorine gas through a solution of iodobenzeneIodobenzene
Iodobenzene is an organic compound consisting of a benzene ring substitituted with one iodine atom. It is useful as a synthetic intermediate in organic chemistry.-Preparation:...
in chloroform
Chloroform
Chloroform is an organic compound with formula CHCl3. It is one of the four chloromethanes. The colorless, sweet-smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous...
, from which it precipitates. The same reaction has been reported at pilot plant scale (20 kg) as well.
- PhI + Cl2 → PhICl2
An alternate preparation involving the use of chlorine
Chlorine
Chlorine is the chemical element with atomic number 17 and symbol Cl. It is the second lightest halogen, found in the periodic table in group 17. The element forms diatomic molecules under standard conditions, called dichlorine...
generated in situ by the action of sodium hypochlorite on hydrochloric acid
Hydrochloric acid
Hydrochloric acid is a solution of hydrogen chloride in water, that is a highly corrosive, strong mineral acid with many industrial uses. It is found naturally in gastric acid....
has also been described.
Reactions
Iodobenzene dichloride is hydrolyzed by basic solutions to give iodosobenzeneIodosobenzene
Iodosobenzene or iodosylbenzene is an organoiodine compound with the empirical formula C6H5IO. This colourless solid compound is used as an oxo transfer reagent in research laboratories examining organic and coordination chemistry...
(PhIO), and is oxidized by sodium hypochlorite to give iodoxybenzene (PhIO2).
In organic synthesis
Organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...
, iodobenzene dichloride is used as a reagent for the selective chlorination of alkene
Alkene
In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond...
s and alkyne
Alkyne
Alkynes are hydrocarbons that have a triple bond between two carbon atoms, with the formula CnH2n-2. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC nomenclature...
s.