1483-72-3

Basic information

• Product Name: DIPHENYLIODONIUM CHLORIDE
• Synonyms: DIPHENYLIODONIUM CHLORIDE;chlorodiphenyliodonium;diphenyl-iodoniuchloride;Iodonium,diphenyl-,chloride;Iodonium,diphenyl-chloride;DIPHENYLIODONIUM CHLORIDE 97%;Diphenyliodonium;Diphenyliodonium chloride, 98+%
• CAS NO: 1483-72-3
• Molecular Formula: C₁₂H₁₀I*Cl
• Molecular Weight: 316.57
• EINECS: 216-049-8
• Product Categories: Diphenyliodonium Compounds;Hypervalent Iodine Compounds;Iodonium Sulfonium & Oxonium Compounds;Synthetic Organic Chemistry;Hypervalent Iodine;Oxidation;Synthetic Reagents
• Mol File: 1483-72-3.mol

Chemical Properties

• Melting Point: 233-235 °C (subl.)(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: White to light cream-yellow/Powder
• Density: 1.6151 (estimate)
• Storage Temp.: 0-6°C
• Solubility: soluble in Methanol
• Water Solubility: Soluble in water and methanol.
• Sensitive: Light Sensitive
• Merck: 14,7464
• BRN: 3574977
• CAS DataBase Reference: DIPHENYLIODONIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DIPHENYLIODONIUM CHLORIDE(1483-72-3)
• EPA Substance Registry System: DIPHENYLIODONIUM CHLORIDE(1483-72-3)

Safety Data

• Hazard Codes: T,Xi
• Statements: 25-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: NN6651666
• F: 8
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1483-72-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Diphenyliodonium chloride is used as a reagent for electrophilic phenylation, which is a crucial step in the synthesis of various organic compounds. It is also employed in the preparation of acetylenic arylselenide and (arylmethylene)oxindoles, contributing to the development of new chemical structures and compounds.
Used in Copper-Catalyzed Cross-Coupling Reactions:
In the field of organic chemistry, DPI is used as a reactant for copper-catalyzed cross-coupling reactions of purines and diaryliodonium salts. These reactions are essential for the synthesis of complex organic molecules, including pharmaceuticals and natural products.
Used in Sonogashira Coupling Reactions:
Diphenyliodonium chloride is utilized in Sonogashira coupling reactions for the preparation of aryl alkynes. This reaction is a significant method for forming carbon-carbon bonds, which are vital in the synthesis of various organic compounds, including those with potential applications in materials science and pharmaceuticals.
Used in Arylation of Anilines:
DPI is also involved in the arylation of anilines, a process that allows for the introduction of aryl groups into the aniline molecule. This reaction is crucial for the synthesis of various aromatic compounds, which have applications in the chemical, pharmaceutical, and materials industries.
Used in Photochemistry:
Diphenyliodonium chloride is employed in studies on the visible-light photosensitive system-dlourescein yellow-bis(di-Ph iodonium) and investigating the properties of direct and sensitized photolysis of dispersed photoacid generators. These studies contribute to the understanding of photochemical processes and the development of new photochemical applications.

InChI:InChI=1/C12H10I/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H/q-1

Upstream product

• 932-72-9 (Dichloroiodo)benzene 
• 67-64-1 acetone 
• 587-85-9 diphenylmercury(II) 
• 71-43-2 benzene 
• 591-51-5 phenyllithium 
• 64146-77-6 tetraphenyl-boric acid ; diphenyliodonium-salt 
• 1483-73-4 diphenyliodonium bromide 
• 2217-79-0 diphenyliodonium iodide 
• 7732-18-5 water 
• 7647-01-0 hydrogenchloride 
• 536-80-1 iodosylbenzene 
• 591-50-4 iodobenzene 

Downstream Products

• 1008-88-4 3-phenylpyridine 
• 1008-89-5 2-phenylpyridine 
• 939-23-1 p-phenylpyridine 
• 591-50-4 iodobenzene 
• 34317-61-8 S-phenyl-L-cysteine 
• 103161-67-7 2-benzoyl-1,2,3-triphenyl-propane-1,3-dione 
• 1206-36-6 diphenyltellurium dichloride 
• 1202-36-4 diphenyl telluride 
• 100-56-1 phenylmercury(II) chloride 
• 108-90-7 chlorobenzene 
• 103-04-8 (phenylthio)acetic acid 
• 92582-40-6 (+/-)-2-Methyl-2-phenyl-3-oxo-bernsteinsaeure-diethylester 
• 60200-80-8 ethyl 2-phenoxy-3,3,3-trifluoro-2-trifluoromethylpropionate 
• 5467-22-1 ethyl triphenylacetate 

Relevant articles and documents

Halogen exchange via a halogenation of diaryliodonium salts with cuprous halide

An efficient halogenation reaction has been developed with diaryliodonium salts and cuprous halides. Various diaryliodonium salts 1 could perform the reaction with readily available CuBr or CuCl in CH3CN at 80°C, assembling bromoarenes or chloroarenes in up to 92% yields. This provides us a method for the transformation from iodoarenes to other haloarenes.

CuBr catalyzed C-N cross coupling reaction of purines and diaryliodonium salts to 9-arylpurines

CuBr was found to be an efficient catalyst for the C-N cross coupling reaction of purine and diaryliodonium salts. 9-Arylpurines were synthesized in excellent yields with short reaction times (2.5 h). The method represents an alternative to the synthesis of 9-arylpurines via Cu(ii) catalyzed C-N coupling reaction with arylboronic acids as arylating agents. The Royal Society of Chemistry 2011.

Synthesis of primary-alkyl selenols and selenides from primary-alkyl thiols involving diphenyl sulfonium salts

Hexyl thiol has been transformed to hexyl selenol and related selenides and selenocyanate by substitution of the corresponding hexyldiphenylsulfonium tetrafluoroborate with selenium nucleophiles. The Royal Society of Chemistry 2005.

Oxidative Anion Metatheses in Diaryliodonium Iodides and Chlorides

Oxidative anion metatheses in the crude title iodides and chlorides produced the corresponding pure hydrogensulfates, nitrates, tetrafluoroborates, triflates, tosylates, as well as bromides and chlorides (only from the iodides) in 54-86% yields. These procedures are easier and shorter than earlier methods. By using modified oxidative metatheses in the title iodides (in the presence of HBr or HCl) it was possible either to isolate, or to detect only, the intermediate dihaloiodates(I). [Ar2I]+[IX2]- (X = Br or Cl). A complex Ph2I+Cl- -1/2I2 was also obtained in 56% yield. Tetraethylammonium iodide was similarly converted into pure tetrafluoroborate or dibromoiodate(I) in 75 and 76% yields, respectively.

A short-cut synthesis of diaryliodonium bromides followed by oxidative anion metatheses

This paper reports a one-pot synthesis of the title bromides (in 20-88% crude yields) from iodoarenes oxidized with the CrO3/AcOH/Ac2O/H2SO4 liquid mixture, then coupled in situ with arenes and, finally, precipitated out with a KBr solution. Similarly, diaryliodonium perchlorates and iodides are obtained in 40-89% crude yields. Oxidative anion metatheses in the crude title bromides produce the respective pure diaryliodonium tetrafluoroborates, tosylates, trifluoroacetates, hydrosulfates, nitrates, and chlorides in 57-80% yields. These new preparative procedures are easier and shorter than many earlier methods.

Diaryliodonium salts

Cationic polymerization of epoxy monomers or prepolymers can be achieved by use of certain radiation sensitive aromatic halonium salts. Curable compositions are provided which can be used as sealants, coating compounds, encapsulants, etc.