(Diacetoxyiodo)benzene Chemical Properties

Melting point:

161-163 °C (lit.)

Density 

1.6865 (estimate)

refractive index 

n/D 1.444

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

INSOLUBLE

form 

Solution

color 

Clear to cloudy colorless to yellow

biological source

mouse

Water Solubility 

INSOLUBLE

Sensitive 

Light Sensitive

BRN 

1879369

Stability:

Light and Moisture sensitive

InChIKey

ZBIKORITPGTTGI-UHFFFAOYSA-N

CAS DataBase Reference

3240-34-4(CAS DataBase Reference)

NIST Chemistry Reference

Iodobenzene diacetate(3240-34-4)

EPA Substance Registry System

Iodine, bis(acetato-.kappa.O)phenyl- (3240-34-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-37/39-26-36/37/39-27

RIDADR 

1479

WGK Germany 

3

RTECS 

DA3525000

F 

4.10-8

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29310095

MSDS

• Language:English Provider:(Diacetoxyiodo)benzene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

(Diacetoxyiodo)benzene Usage And Synthesis

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

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

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