Chemical Properties
white to light yellow crystal powder
Uses
(Diacetoxyiodo)benzene is a hypervalent iodine reagent that is used in conjunction with catalytic amount of sodium azide in acetonitrile, which enables oxidative decarboxylation of 2-aryl carboxylic acid into the corresponding aldehydes, ketones and nitriles.
Application
(Diacetoxyiodo)benzene, an oxidizing agent, has a wide range of applications. (Diacetoxyiodo)benzene, also known as Diacetoxy Iodobenzene, is used in wide range of medicals industrial applications as well as in human and animal nutrition products such as antiseptics and disinfectants, pharmaceutical intermediates, polarizing films for liquid crystal display [LCD] chemicals.
Origin
This reagent was originally prepared by Conrad Willgerod by reacting iodobenzene with a mixture of acetic acid and peracetic acid：
C6H5I + CH3CO3H + CH3CO2H → C6H5I(O2CCH3)2 + H2O
Purification Methods
The purity of diacetoxyiodobenzene can be checked by treatment with H2SO4 then KI and the liberated I2 is estimated with standard thiosulfate. It has been recrystallised from 5M acetic acid and dried overnight in a vacuum desiccator over CaCl2. The surface of the crystals may become slightly yellow but this does not affect its usefulness. [Sharefkin & Saltzman Org Synth Coll Vol V 600 1973, Beilstein 5 IV 693.]
