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Merck
CN

43088

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
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
57650143
EC Number:
216-049-8
Beilstein/REAXYS Number:
3574977
MDL number:
MFCD00011909

Key Documents

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Product Name

Diphenyliodonium chloride, ≥98.0% (AT)

InChI key

RSJLWBUYLGJOBD-UHFFFAOYSA-M

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

SMILES string

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

assay

≥98.0% (AT)

reaction suitability

reagent type: oxidant

mp

233-235 °C (subl.) (lit.)

functional group

iodo

Quality Level

200

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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

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory 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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN4005
BCCL7101
BCCJ8743
BCCF7000
BCCB1671

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The Journal of Organic Chemistry, 4117-4117 (1987)
Z.-C. Chen et al.
The Journal of Organic Chemistry, 52, 4115-4115 (1987)
Synthesis, 723-723 (1988)
Sarah A Krawczyk et al.
PloS one, 7(4), e34904-e34904 (2012-04-12)
In obesity, there is an increase in reactive oxygen species (ROS) within adipose tissue caused by increases in inflammation and overnutrition. Hormone sensitive lipase (HSL) is part of the canonical lipolytic pathway and critical for complete lipolysis. This study hypothesizes
Li Qian et al.
Parkinsonism & related disorders, 13 Suppl 3, S316-S320 (2008-11-19)
In this paper we report that diphenyliodonium (DPI), a NADPH oxidase inhibitor, shows potent anti-inflammatory and neuroprotective effects at femtomolar concentrations (10(-13) to 10(-14) M) in primary midbrain cultures. Mechanistic studies revealed that DPI-elicited effects were mediated by the inhibition
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