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902772

Sigma-Aldrich

(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
MDL number:
MFCD00008692
UNSPSC Code:
12352002

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

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

Application

Stoichiometric oxidant in the TEMPO oxidation of nerol to neral.[1] Oxidant employed in the rhodium-catalyzed aziridination of olefins with sulfamate esters.[2]
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.[3]
Used in the room temperature Pd-catalyzed 2-arylation of indoles
Useful reagent for the synthesis of a wide variety of heterocyclic compounds.[4][5]

Other Notes

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

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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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Jinbo Huang et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(44), 13964-13967 (2012-09-22)
A metal-free synthesis of diversified benzimidazoles from N-arylamidines through a phenyliodine(III) diacetate (PIDA) promoted intramolecular direct C(sp(2))-H imidation has been developed. The reaction proceeds smoothly at 0 °C or ambient temperature to provide the desired products in good to excellent
Lopa V Desai et al.
Journal of the American Chemical Society, 126(31), 9542-9543 (2004-08-05)
This communication describes a new palladium-catalyzed method for the oxygenation of unactivated sp3 C-H bonds. A wide variety of alkane substrates containing readily available oxime and/or pyridine directing groups are oxidized with extremely high levels of chemo-, regio-, and in
Synlett, 221-221 (1994)
Jayasree Seayad et al.
Organic letters, 12(7), 1412-1415 (2010-03-13)
Copper(I) or -(II) salts with weakly coordinating anions catalyze the diacetoxylation of olefins efficiently in the presence of PhI(OAc)(2) as the oxidant under mild conditions. The reaction is effective for aryl, aryl alkyl, as well as aliphatic terminal and internal
Substrate dependence of nonlinear effects: mechanistic probe and practical applications.
Y K Chen et al.
Journal of the American Chemical Society, 123(22), 5378-5379 (2001-07-18)
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