Iodosobenzene

Names

IUPAC name

Iodosylbenzene

Other names

Iodosobenzene

Identifiers

CAS Number

536-80-1^Y

3D model (JSmol)

Interactive image

ChemSpider

83171^Y

ECHA InfoCard

100.007.864

PubChem CID

92125

InChI

InChI=1S/C6H5IO/c8-7-6-4-2-1-3-5-6/h1-5H^Y

Key: JYJVVHFRSFVEJM-UHFFFAOYSA-N^Y
InChI=1/C6H5IO/c8-7-6-4-2-1-3-5-6/h1-5H

Key: JYJVVHFRSFVEJM-UHFFFAOYAR

SMILES

c1ccc(cc1)I=O

Properties

Chemical formula

C₆H₅IO

Molar mass

220.01 g mol⁻¹

Appearance

colourless solid

Density

1.229 g cm⁻³

Melting point

210 ˚C

Solubility in water

poor

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

Infobox references

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. It is related to the more popular reagent periodinane.

Iodosobenzene was first described by Conrad Willgerodt from iodobenzene. It is prepared by first oxidizing iodobenzene to the diacetate followed by hydrolysis:

The structure of iodosobenzene remains unverified crystallographically. Its low solubility in most solvents and vibrational spectroscopy indicate that it is not molecular, but is polymeric, consisting of I-O-I-O chains. The related diacetate, C₆H₅I(O₂CCH₃)₂, illustrates the ability of iodine(III) to adopt a T-shaped geometry without multiple bonds. Theoretical studies show that the bonding between the iodine and oxygen atoms in iodosobenzene represents a single dative I-O sigma bond, confirming the absence of the double I=O bond.

Iodosobenzene has no commercial uses, but in the laboratory it is employed as an "oxo-transfer reagent." It epoxidizes certain alkenes and converts some metal complexes into the corresponding oxo derivatives. Although it is an oxidant, it is also mildly nucleophilic. The active agent in these oxo-transfer reactions is assumed to be monomeric PhI=O, but this aspect remains unverified.

This compound is explosive and should not be heated under vacuum.

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