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(Diacetoxyiodo)benzene

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(Diacetoxyiodo)benzene Basic information

Product Name:
(Diacetoxyiodo)benzene
Synonyms:
  • PHENYLIODINE DIACETATE
  • PIA
  • AURORA KA-6690
  • (DIACETOXYIODO)BENZENE
  • DIACETOXYIODOSOBENZENE
  • DAIB
  • LABOTEST-BB LT00847235
  • IODOBENZENE I,I-DIACETATE
CAS:
3240-34-4
MF:
C10H11IO4
MW:
322.1
EINECS:
221-808-1
Product Categories:
  • APIs
  • Benzene derivatives
  • Hypervalent Iodine Compounds
  • Oxidation
  • Synthetic Organic Chemistry
  • bc0001
Mol File:
3240-34-4.mol
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(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
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)
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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
4.10-8
Hazard Note 
Irritant
TSCA 
Yes
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29310095

MSDS

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(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

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.]

(Diacetoxyiodo)benzene Preparation Products And Raw materials

Raw materials

(Diacetoxyiodo)benzeneSupplier

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