10294. Iodobenzene Dichloride

Nomenclature

CAS number: 932-72-9
(Dichloroiodo)benzene; benzene iododichloride.
C6H5Cl2I; mol wt 274.91.
C 26.21%, H 1.83%, Cl 25.79%, I 46.16%.

Description and references

First reported hypervalent iodine compd; utilized primarily as chlorinating reagent. Prepn from iodobenzene and chlorine gas: C. Willgerodt, Chem. Zentralbl. 56, 833 (1885); idem, J. Prakt. Chem. 33, 154 (1886) DOI; H. L. Lucas, E. R. Kennedy, Org. Synth. coll. vol. III, 482 (1955). Large scale prepn: A. Zanka et al., Org. Process Res. Dev. 2, 270 (1998) DOI. Synthetic applications: D. H. R. Barton et al., Tetrahedron 48, 8881 (1992) DOI; and new prepn methodology: X.-F. Zhao, C. Zhang, Synthesis 2007, 551 DOI. Crystal structure: E. M. Archer, T. G. D. Van Schalkwyk, Acta Crystallogr. 6, 88 (1953) DOI; J. V. Carey et al., J. Chem. Res. Synop. 1996, 358. Review: Z. Wu, Synlett 2008, 782-783 DOI.

Chemical structure

Properties

Yellow monoclinic needles, mp 112-113° (Zhou). Also reported as mp 113-117° (dec) (Zanka). Crystal density: 2.2 g/cm3. Decomposes fairly rapidly when exposed to air and uv light.

Use

In synthetic organic chemistry, primarily as a chlorinating and oxidizing reagent. Also used in other synthetic transformations.