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Key Documents

43088

Sigma-Aldrich

Diphenyliodonium chloride

≥98.0% (AT)

Synonym(s):

DPI, NSC 134275

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About This Item

Linear Formula:
(C6H5)2I+Cl-
CAS Number:
Molecular Weight:
316.57
Beilstein:
3574977
EC Number:
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥98.0% (AT)

reaction suitability

reagent type: oxidant

mp

233-235 °C (subl.) (lit.)

functional group

iodo

SMILES string

[Cl-].[I+](c1ccccc1)c2ccccc2

InChI

1S/C12H10I.ClH/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;/h1-10H;1H/q+1;/p-1

InChI key

RSJLWBUYLGJOBD-UHFFFAOYSA-M

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Application

Reactant for:
  • Copper-catalyzed cross coupling reactions of purines and diaryliodonium salts
  • Synthesis of acetylenic arylselenides
  • Sonogashira coupling reactions for the preparation of aryl alkynes
  • C-H functionalization for synthesis of (arylmethylene)oxindoles
  • Arylation of anilines
  • Studies on the visible-light photosensitive system-dlourescein yellow-bis(di-Ph iodonium)
  • Investigating the properties of direct and sensitized photolysis of dispersed photoacid generators

Other Notes

Reagent used for electrophilic phenylation, e.g. of malonates and dithiocarboxylates

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory 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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Z.-C. Chen et al.
The Journal of Organic Chemistry, 52, 4115-4115 (1987)
The Journal of Organic Chemistry, 4117-4117 (1987)
Synthesis, 723-723 (1988)
Tao Ma et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 31(15), 5589-5595 (2011-04-15)
Generation of reactive oxygen species (ROS) causes cellular oxidative damage and has been implicated in the etiology of Alzheimer's disease (AD). In contrast, multiple lines of evidence indicate that ROS can normally modulate long-term potentiation (LTP), a cellular model for
T Franck et al.
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Neutrophil (PMN) contribution to the acute inflammatory processes may lead to an excessive generation of reactive oxygen metabolites species (ROS) and secretion of granule enzymes. We compared the effects of either phorbol myristate acetate (PMA) or N-formyl-methionyl-leucyl-phenylalanine (fMLP) in combination

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