Diphenyliodonium chloride

Base Information

• Chemical Name: Diphenyliodonium chloride
• CAS No.: 1483-72-3
• Deprecated CAS: 17267-18-4,935753-03-0,1022162-08-8,1189975-37-8
• Molecular Formula: C12H10 I . Cl
• Molecular Weight: 316.569
• Hs Code.: 29319090
• European Community (EC) Number: 216-049-8
• DSSTox Substance ID: DTXSID60883679
• ChEMBL ID: CHEMBL481680
• Mol file: 1483-72-3.mol

Synonyms:diphenyliodonium;diphenyliodonium bromide;diphenyliodonium chloride;diphenyliodonium hexafluoroarsenate;diphenyliodonium hexafluorophosphate;diphenyliodonium iodide;diphenyliodonium nitrate;diphenyliodonium nitrite;diphenyliodonium sulfate (1:1);diphenyliodonium tosylate;iodonium biphenyl;iodoniumdiphenyl

Chemical Property of Diphenyliodonium chloride

Chemical Property:

• Appearance/Colour: WHITE TO LIGHT CREAM-YELLOW POWDER
• Melting Point: 233-235 °C (subl.)(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: g/cm³
• LogP: -3.18100
• Storage Temp.: 0-6°C
• Sensitive.: Light Sensitive
• Solubility.: soluble in Methanol
• Water Solubility.: Soluble in water and methanol.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 315.95158
• Heavy Atom Count: 14
• Complexity: 116

Purity/Quality:

98%,99%, ^*data from raw suppliers

Diphenyliodonium chloride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T,Xi
• Statements: 25-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)[I+]C2=CC=CC=C2.[Cl-]
• Uses: Diphenyliodonium chloride is used as a reagent for electrophilic phenylation . It is used as a reactant for copper-catalyzed cross coupling reactions of purinesband arylation of anilines. It is involved in the preparation of acetylenic arylselenide and (arylmethylene)oxindoles. Further, it is employed in the preparation of aryl alkynes through Sonogashira coupling reactions. Reactant for:Copper-catalyzed cross coupling reactions of purines and diaryliodonium saltsSynthesis of acetylenic arylselenidesSonogashira coupling reactions for the preparation of aryl alkynesC-H functionalization for synthesis of (arylmethylene)oxindolesArylation of anilinesStudies on the visible-light photosensitive system-dlourescein yellow-bis(di-Ph iodonium)Investigating the properties of direct and sensitized photolysis of dispersed photoacid generators

Technology Process of Diphenyliodonium chloride

There total 24 articles about Diphenyliodonium chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → diphenyliodonium chloride (1483-72-3)

Guidance literature:

benzene; With potassium iodate; acetic anhydride;

With sulfuric acid; acetic acid;

With ammonium chloride;

DOI:10.1039/b418026g

Reference yield: 73.0%

diphenyliodonium iodide (2217-79-0) → diphenyliodonium chloride (1483-72-3)

Guidance literature:

With hydrogenchloride; dihydrogen peroxide; In methanol; water; Heating;

DOI:10.1246/bcsj.70.219

Reference yield: 63.0%

diphenyliodonium bromide (1483-73-4) → diphenyliodonium chloride (1483-72-3)

Guidance literature:

With hydrogenchloride; dihydrogen peroxide; In methanol; cyclohexene; Heating;

DOI:10.1055/s-1995-4045

upstream raw materials:

(Dichloroiodo)benzene

acetone

diphenylmercury(II)

benzene

Downstream raw materials:

3-phenylpyridine

2-phenylpyridine

p-phenylpyridine

iodobenzene

Refernces

• 1、 Li, Jian,Liu, Li,Ding, Dong,Sun, Jiang-Tao. "Halogen exchange via a halogenation of diaryliodonium salts with cuprous halide". . p. 541 - 548. Retrieved 2014/01/06.
• 2、 Krief, Alain,Dumont, Willy,Robert, Michael. "Synthesis of primary-alkyl selenols and selenides from primary-alkyl thiols involving diphenyl sulfonium salts". . p. 2167 - 2168. Retrieved 2007/10/03.