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 a
cid 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
reaction suitability
reagent type: catalyst
reagent type: oxidant
reaction type: C-H Activation
Biological Activity
RPTOR independent companion of MTOR complex 2 (RICTOR) maintains stability of the mechanistic target of rapamycin (mTOR) complex 2. It also has a role in neutrophil chemotaxis and has been linked to prostate cancer.
Synthesis
GENERAL STEPS: In a typical experiment, glacial acetic acid (2 mL), iodobenzene (0.401 mmol), and cobalt chloride hexahydrate (0.004 mmol, 1 mol%) were added to a 20 mL scintillation vial and a rubber septum was assembled. The reaction vessel was purged with oxygen for 5 min, and then acetaldehyde (4.07 mmol, 10.2 eq.) was added all at once. The reaction mixture was stirred at 1 atmosphere of oxygen and reacted at 23°C for 5 h via an inflated balloon. After completion of the reaction, the solvent was removed under vacuum and the residue was dissolved in dichloromethane. The organic layer was washed with distilled water and extracted with dichloromethane (3 x 7 mL). The organic layers were combined, dried with anhydrous magnesium sulfate and the solvent was removed in vacuum to give iodobenzene diacetic acid. The isolated compounds were characterized by 1H NMR and 13C NMR spectroscopy.
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.]
References
[1] Nature Chemistry, 2018, vol. 10, # 2, p. 200 - 204
