Iodobenzene dichloride

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.

Iodobenzene dichloride[1]
Names
IUPAC name
(Dichloro-λ3-iodanyl)benzene
Other names
Iodosobenzene dichloride; Phenyliodine(III) dichloride; Phenyliodo dichloride; Phenyliodoso chloride; Phenylchloroiodonium chloride; Dichloroiodobenzene; Iododichlorobenzene
Identifiers
3D model (JSmol)
Abbreviations IBD
ChemSpider
UNII
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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Infobox references

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][3]

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.[4] The same reaction has been reported at pilot plant scale (20 kg) as well.[5]

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.[6]

Reactions

Iodobenzene dichloride is hydrolyzed by basic solutions to give iodosobenzene (PhIO),[7] and is oxidized by sodium hypochlorite to give iodoxybenzene (PhIO2).[8]

In organic synthesis, iodobenzene dichloride is used as a reagent for the selective chlorination of alkenes[1] and alkynes.[9]

References
  1. Phenyliodine(III) Dichloride, David W. Knight and Glen A. Russell, in Encyclopedia of Reagents for Organic Synthesis, 2001, John Wiley & Sons, Ltd doi:10.1002/047084289X.rp071
  2. E. M. Archer and T. G. van Schalkwy (1953). "The crystal structure of benzene iododichloride". Acta Crystallogr. 6: 88–92. doi:10.1107/S0365110X53000193.
  3. J. V. Carey; P. A. Chaloner; P. B. Hitchcock; T. Neugebauer; K. R. Seddon (1996). "Synthesis and decomposition of dichloroiodoarenes - An improved low temperature X-ray structure of dichloroiodobenzene and the structure OFORO-2,3,5,6-TETRAKIS(CHLOROMETHYL)-4-METHYLBENZENE". J. Chem. Res. 358 (8): 2031–.
  4. H. J. Lucas and E. R. Kennedy. "Iodobenzene dichloride". Organic Syntheses.; Collective Volume, 3, p. 482
  5. Zanka, Atsuhiko; Takeuchi, Hiroki; Kubota, Ariyoshi (1998). "Large-Scale Preparation of Iodobenzene Dichloride and Efficient Monochlorination of 4-Aminoacetophenone". Organic Process Research & Development. 2 (4): 270. doi:10.1021/op980024e.
  6. Zhao, Xue-Fei; Zhang, Chi (2007). "Iodobenzene Dichloride as a Stoichiometric Oxidant for the Conversion of Alcohols into Carbonyl Compounds; Two Facile Methods for Its Preparation". Synthesis. 2007 (4): 551. doi:10.1055/s-2007-965889.
  7. H. J. Lucas, E. R. Kennedy, and M. W. Formo (1955). "Iodosobenzene". Organic Syntheses.CS1 maint: multiple names: authors list (link); Collective Volume, 3, p. 483
  8. M. W. Formo and John R. Johnson (1955). "Iodoxybenzene: B. Hypochlorite oxidation of iodobenzene dichloride". Organic Syntheses.; Collective Volume, 3, p. 485
  9. Michael E. Jung and Michael H. Parker (1997). "Synthesis of Several Naturally Occurring Polyhalogenated Monoterpenes of the Halomon Class". Journal of Organic Chemistry. 62 (21): 7094–7095. doi:10.1021/jo971371. PMID 11671809.

Further reading
  • Tanner, Dennis D; Van Bostelen, P. B. (1967). "Free-radical chlorination reactions of iodobenzene dichloride". Journal of Organic Chemistry. 32 (5): 1517–1521. doi:10.1021/jo01280a047.
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