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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:
1483-72-3
Molecular Weight:
316.57
Beilstein:
3574977
EC Number:
216-049-8
MDL number:
MFCD00011909
UNSPSC Code:
12352002
PubChem Substance ID:
57650143
NACRES:
NA.22

Quality Level

200

Assay

≥98.0% (AT)

reaction suitability

reagent type: oxidant

mp

233-235 °C (subl.) (lit.)

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
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Z.-C. Chen et al.
The Journal of Organic Chemistry, 52, 4115-4115 (1987)
Synthesis, 723-723 (1988)
The Journal of Organic Chemistry, 4117-4117 (1987)
Aurélien Bigot et al.
Journal of the American Chemical Society, 133(35), 13778-13781 (2011-08-19)
A new strategy for the catalytic enantioselective α-arylation of N-acyloxazolidinones with chiral copper(II)-bisoxazoline complexes and diaryliodonium salts is described. The mild catalytic conditions are operationally simple, produce valuable synthetic building blocks in excellent yields and enantioselectivities, and can be applied
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
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