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(Diacetoxyiodo)benzene

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(Diacetoxyiodo)benzene manufacturers

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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
(Diacetoxyiodo)benzene Structure
(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 sourcemouse
Water Solubility INSOLUBLE
Sensitive Light Sensitive
BRN 1879369
Stability:Light and Moisture sensitive
InChI1S/C10H11IO4/c1-8(12)14-11(15-9(2)13)10-6-4-3-5-7-10/h3-7H,1-2H3
InChIKeyZBIKORITPGTTGI-UHFFFAOYSA-N
SMILESCC(OI(OC(C)=O)C1=CC=CC=C1)=O
CAS DataBase Reference3240-34-4(CAS DataBase Reference)
NIST Chemistry ReferenceIodobenzene diacetate(3240-34-4)
EPA Substance Registry SystemIodine, 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
4.10-8
Hazard Note Irritant
TSCA TSCA listed
HazardClass 6.1(b)
PackingGroup III
HS Code 29310095
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
(Diacetoxyiodo)benzene English
ACROS English
SigmaAldrich English
ALFA English
(Diacetoxyiodo)benzene Usage And Synthesis
Chemical Propertieswhite 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.
OriginThis 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 suitabilityreagent type: catalyst
reagent type: oxidant
reaction type: C-H Activation
Biological ActivityRPTOR 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
Iodobenzene

591-50-4

Acetaldehyde

75-07-0

(Diacetoxyiodo)benzene

3240-34-4

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 MethodsThe 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
Tag:(Diacetoxyiodo)benzene(3240-34-4) Related Product Information
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