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Sku TS246CS-W012024_10_G
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Product Information

Product Name
Diphenyliodonium chloride
Brand Name
ChemScene
Product Number
CS-W012024
CAS
1483-72-3
Certificate of Analysis (COA)​
COA not found

General Information

PubChem CID
73870
IUPAC Name
diphenyliodanium chloride
InChI Key
RSJLWBUYLGJOBD-UHFFFAOYSA-M
SMILES
C1=CC=C(C=C1)I+C2=CC=CC=C2.Cl-

Description

Product Introduction

Diphenyliodonium Chloride contains a positively charged diphenyliodonium center paired with chloride. The electron-deficient iodine center gives this compound useful electrophilic reactivity, allowing it to participate in aryl-transfer and related organic transformations.

In photochemical materials research, diaryliodonium salts are important sources of photo-generated strong acids and are therefore used in cationic polymerization, photoresist chemistry and UV-curable material systems. Diphenyliodonium Chloride is also used as a reagent for electrophilic phenylation and transition-metal-mediated coupling reactions.

 

Mechanism / Principle

Diphenyliodonium Chloride functions primarily through the highly electrophilic diaryliodonium center.

Under suitable reaction or photochemical conditions, the iodonium species can undergo cleavage or aryl-transfer processes, generating reactive intermediates. In organic synthesis, this enables electrophilic phenylation and aryl-transfer reactions. In photopolymerization systems, diaryliodonium salts can generate strong Brønsted acids after photochemical activation, which can initiate cationic polymerization of suitable monomers and resins.

This combination of electrophilic reactivity and photoacid-generating capability makes Diphenyliodonium Chloride useful for organic synthesis and advanced photopolymer materials research.

 

Key Research Applications

1. Electrophilic Phenylation

Diphenyliodonium Chloride can be used as an electrophilic phenylating reagent for introducing phenyl groups into suitable substrates. It provides a useful alternative to conventional aryl halide-based approaches in selected synthetic systems.

 

2. Transition-Metal-Mediated Cross-Coupling

Diaryliodonium salts can participate in metal-catalyzed aryl-transfer reactions. Diphenyliodonium Chloride has been investigated as an arylating reagent in copper-catalyzed and other transition-metal-mediated transformations.

 

3. Organic Synthesis

Diphenyliodonium Chloride can serve as a reactive iodine-containing reagent for the preparation of substituted aromatic compounds and other advanced organic intermediates. Its electrophilic phenyl-transfer characteristics make it useful in synthetic methodology research.

 

4. Photoacid Generator Systems

Diphenyliodonium salts are important photoacid-generating materials. Upon appropriate photochemical activation, they can generate strong acid species that promote acid-catalyzed reactions, making them relevant to photoresist and photochemical material research.

 

5. Cationic Photopolymerization

The photoacid generated from diaryliodonium salts can initiate cationic polymerization of epoxy, oxetane and other suitable monomers. This makes Diphenyliodonium Chloride relevant to UV-curable resin and advanced polymer research.

 

6. Photoresist and Electronic Materials

Photoacid-generating compounds are widely investigated in chemically amplified photoresist systems. Diphenyliodonium Chloride can therefore be studied in photoresist formulation, lithography-related materials and electronic-material development.

 

7. Advanced Functional Materials

Its combination of ionic structure and photoactive behavior makes Diphenyliodonium Chloride useful for research involving UV-responsive polymers, functional coatings, photochemical materials and other advanced material systems.

 

Advantages

  • Effective diaryliodonium reagent for electrophilic aryl transfer.
  • Useful source of reactive phenyl groups in selected organic transformations.
  • Applicable to photochemical and photoacid-generating systems.
  • Relevant to cationic photopolymerization research.
  • Suitable for photoresist and electronic-material development.
  • Useful building block for organic synthesis and functional-material research.
  • Commercial grades with high assay are available for laboratory research. 

 

Storage & Handling

Diphenyliodonium Chloride should be handled as a laboratory research chemical. It is reported to be sensitive to light, air and heat. TCI recommends refrigerated storage at 0–10 °C and storage under inert gas.

Keep the container tightly closed and minimize exposure to light, moisture and elevated temperatures. Appropriate gloves, eye protection and laboratory ventilation should be used during handling. The compound is classified as toxic if swallowed and may cause skin and eye irritation; consult the current SDS before use.

 

Research Areas

  • Organic Synthesis
  • Photochemistry
  • Photopolymerization Materials
  • Photoresist Materials
  • Electronic Materials
  • UV-Curable Polymer Materials
  • Functional Coatings
  • Advanced Polymer Research
  • Fine Chemical Research

FAQ

Q1. What is Diphenyliodonium Chloride?
Diphenyliodonium Chloride is a diaryliodonium salt with CAS 1483-72-3. It is used in organic synthesis, electrophilic phenylation, photochemistry and photoacid-generating systems.

 

Q2. What is Diphenyliodonium Chloride used for?
It is used in electrophilic phenylation, organic synthesis, cross-coupling research, photoacid generation, cationic photopolymerization and photoresist materials.

 

Q3. Can Diphenyliodonium Chloride be used in photopolymerization?
Yes. Diaryliodonium salts can function as photoacid-generating components for cationic polymerization systems, including research involving epoxy and other cationically polymerizable materials.

 

Q4. Is Diphenyliodonium Chloride used in photoresist research?
Yes. Diphenyliodonium salts are relevant to photoacid generator systems used in photoresist and lithography-related materials research.

 

Q5. What is the physical form of Diphenyliodonium Chloride?
It is typically supplied as a white to light yellow powder or crystalline solid.

 

Q6. How should Diphenyliodonium Chloride be stored?
It should generally be protected from light, air and heat. TCI specifies refrigerated storage at 0–10 °C under inert gas.

 

Q7. What is the melting point of Diphenyliodonium Chloride?
Its reported melting point is approximately 233–235 °C, with decomposition/sublimation noted in some references.