Iodobenzene dichloride

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Iodobenzene dichloride[1]
Names
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
)
Abbreviations IBD
ChemSpider
UNII
  • Cl[I](c1ccccc1)Cl
Properties
C6H5Cl2I
Molar mass 274.91 g·mol−1
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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Iodobenzene dichloride (PhICl2) is a complex of

chlorinating agent
.

Chemical structure

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 → 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

iodoxybenzene (PhIO2).[7]

In organic synthesis, iodobenzene dichloride is used as a reagent for the selective chlorination of alkenes.[1] and alkynes.[8]

References

  1. ^
    doi:10.1002/047084289X.rp071
  2. doi:10.1107/S0365110X53000193
    .
  3. doi:10.15227/orgsyn.022.0069
    .
  4. doi:10.1021/op980024e
    .
  5. doi:10.1055/s-2007-965889
    .
  6. doi:10.15227/orgsyn.022.0070{{cite journal}}: CS1 maint: multiple names: authors list (link
    ).
  7. doi:10.15227/orgsyn.022.0072
    .
  8. PMID 11671809
    .

Further reading
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