Iodobenzene dichloride
Chemical compound
From Wikipedia, the free encyclopedia
Iodobenzene dichloride (PhICl2) is a complex of iodobenzene with chlorine. As a reagent for organic chemistry, it is used as an oxidant and chlorinating agent.
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| Names | |||
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| Preferred IUPAC name
Dichloro(phenyl)-λ3-iodane | |||
| Other names
Iodosobenzene dichloride; Phenyliodine(III) dichloride; Phenyliodo dichloride; Phenyliodoso chloride; Phenylchloroiodonium chloride; Dichloroiodobenzene; Iododichlorobenzene | |||
| Identifiers | |||
3D model (JSmol) |
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| Abbreviations | IBD | ||
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PubChem CID |
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| UNII | |||
CompTox Dashboard (EPA) |
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| Properties | |||
| C6H5Cl2I | |||
| Molar mass | 274.91 g·molâ1 | ||
| Appearance | Yellow solid | ||
| Density | 2.2 g/cm3 | ||
| Melting point | 115 to 120 °C (239 to 248 °F; 388 to 393 K) (decomposes) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical structure
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.[2]
Preparation
Iodobenzene dichloride is not stable and is not commonly available commercially. It is prepared by passing chlorine gas through a solution of iodobenzene in chloroform, from which it precipitates.[3] The same reaction has been reported at pilot plant scale (20 kg) as well.[4]
- Ph-I + Cl2 â PhICl2
An alternate preparation involving the use of chlorine generated in situ by the action of sodium hypochlorite on hydrochloric acid has also been described.[5]
Reactions
Iodobenzene dichloride is hydrolyzed by basic solutions to give iodosobenzene (PhIO)[6] and is oxidized by sodium hypochlorite to give iodoxybenzene (PhIO2).[7]
In organic synthesis, iodobenzene dichloride is used as a reagent for the selective chlorination of alkenes[1] and alkynes.[8]