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Merck
CN

902772

(Diacetoxyiodo)benzene solution

0.50 M solution in DCM

Synonym(s):

Iodobenzene diacetate, Iodosobenzene diacetate, Phenyl-iodanediyl diacetate

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About This Item

Linear Formula:
C10H11IO4
CAS Number:
3240-34-4
UNSPSC Code:
12352002
MDL number:
MFCD00008692

Key Documents

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InChI

1S/C10H11IO4/c1-8(12)14-11(15-9(2)13)10-6-4-3-5-7-10/h3-7H,1-2H3

InChI key

ZBIKORITPGTTGI-UHFFFAOYSA-N

form

liquid

reaction suitability

reaction type: C-H Activation, reagent type: catalyst, reagent type: oxidant

refractive index

n/D 1.444

density

1.361 g/mL

Application

Stoichiometric oxidant in the TEMPO oxidation of nerol to neral. Oxidant employed in the rhodium-catalyzed aziridination of olefins with sulfamate esters.
Unactivated sp3 C-H bonds of both oxime and pyridine substrates undergo highly regio- and chemoselective Pd(II)-catalyzed oxygenation with PhI(OAc)2 as a stoichiometric oxidant.
Used in the room temperature Pd-catalyzed 2-arylation of indoles
Useful reagent for the synthesis of a wide variety of heterocyclic compounds.

Other Notes

Rh2(esp)2: An Exceptionally Efficient and Selective Catalyst for C-H Amination

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Central nervous system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Tetrahedron, 62, 11331-11331 (2006)
S Garadnay et al.
Current medicinal chemistry, 8(6), 621-626 (2001-04-03)
The reactions of morphine and its derivatives with phenyliodo(III)diacetate (PIDA) have been studied. This methodology has not been introduced to morphine alkaloids, despite the fact that such a strategy would ensure dearomatization of the electrophilic aromatic ring of morphine derivatives
Renhua Fan et al.
Organic & biomolecular chemistry, 6(24), 4615-4621 (2008-11-29)
An efficient one-pot oxidative decarboxylation-Friedel-Crafts reaction of acyclic alpha-amino acid derivatives with electron-rich aromatic compounds is reported. The reaction is activated by the combination of iodobenzene diacetate, iodine and iron dust, resulting in a mild and simple reaction system. The
Hai Yi et al.
Chemical communications (Cambridge, England), 46(37), 6941-6943 (2010-08-24)
3-Aryl-4-unsubstituted-6-CF(3)-pyridin-2-ones have been efficiently synthesized from readily available 4-aryl-3-carbamoyl-6-CF(3)-pyridin-2(1H)-ones by treatment with PhI(OAc)(2) in the presence of NaOH.
Aldrichimica Acta, 27, 15-15 (1994)
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