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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. 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

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Description
Pricing

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H336,H351

Hazard Classifications

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

Target Organs

Central nervous system

Storage Class Code

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

Certificates of Analysis (COA)

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Tetrahedron, 62, 11331-11331 (2006)
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
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
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
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.
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