58109-40-3

Basic information

• Product Name: Diphenyliodonium hexafluorophosphate
• Synonyms: DIHFP;diphenyliodoniuM hexafluorophosphate(V);DPIHFP;iodonium diphenyl hexafluorophosphate;DIHP;DIPHENYLIODINIUM HEXAFLUOROPHOSPHATE;DIPHENYLIODONIUM HEXAFLUOROPHOSPHATE;diphenyl-iodoniuhexafluorophosphate(1-)
• CAS NO: 58109-40-3
• Molecular Formula: C₁₂H₁₀I*F₆P
• Molecular Weight: 426.08
• EINECS: 261-134-5
• Product Categories: Diphenyliodonium Compounds;Functional Materials;Hypervalent Iodine Compounds;Iodonium Sulfonium & Oxonium Compounds;Photopolymerization Initiators;Synthetic Organic Chemistry;Hypervalent Iodine;Oxidation;Synthetic Reagents;Cationic PhotoinitiatorsMicro/Nanoelectronics;FluoridesSelf Assembly&Contact Printing;Electronic Chemicals;Organic Photoinitiators;Photoacid Generators (PAGs);Photoresists;Polymerization Initiators
• Mol File: 58109-40-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 140-144 °C(lit.)
• Appearance: /Crystalline
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Soluble in tetrahydrofuran, ethyl acetate, methanol, acetonitril
• Sensitive: Light Sensitive
• BRN: 4343861
• CAS DataBase Reference: Diphenyliodonium hexafluorophosphate(CAS DataBase Reference)
• NIST Chemistry Reference: Diphenyliodonium hexafluorophosphate(58109-40-3)
• EPA Substance Registry System: Diphenyliodonium hexafluorophosphate(58109-40-3)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 1759 8/PG 3
• WGK Germany: 3
• F: 8-10-21
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 58109-40-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 58109-40-3 differently. You can refer to the following data:
1. Catalyst for the photochemical polymerization of various monomers.
2. Diphenyliodonium hexafluorophosphate is used as cationic photoinitiator and photoacid generator. It acts as a catalyst for the photochemical polymerization of various monomers. Further, it used as arylating reagent as well as an oxidant in organic synthesis.

InChI:InChI=1/C12H10I.F6P/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;1-7(2,3,4,5)6/h1-10H;/q+1;-1

Synthetic route

iodobenzene (591-50-4) + benzene (71-43-2) → diphenyliodonium hexafluorophosphate (58109-40-3)

Conditions	Yield
With hexafluorophosphoric acid; 3-chloro-benzenecarboperoxoic acid

diphenyliodonium 4-nitrophenolate → potassium 4-nitrophenolate (1124-31-8) + diphenyliodonium hexafluorophosphate (58109-40-3)

Conditions	Yield
With potassium hexafluorophosphate In acetonitrile at 20℃; Equilibrium constant; Temperature; Inert atmosphere;

diphenyliodonium 4-nitrophenolate + tert-butylammonium hexafluorophosphate(V) (3109-63-5) → tetra-n-butylammonium p-nitrophenoxide (3002-48-0) + diphenyliodonium hexafluorophosphate (58109-40-3)

Conditions	Yield
In acetonitrile at 20℃; Equilibrium constant; Inert atmosphere;

(allylsulfonyl)benzene (16212-05-8) + diphenyliodonium hexafluorophosphate (58109-40-3) → trans-cinnamyl phenyl sulfone (16212-07-0)

Conditions	Yield
With palladium diacetate; sodium hydrogencarbonate In acetonitrile at 50℃; for 22h;	99%

indole (120-72-9) + diphenyliodonium hexafluorophosphate (58109-40-3) → 2-phenyl-indole (948-65-2)

Conditions	Yield
Stage #1: indole With C64H56N6P2Pd2 In acetic acid at 24.84℃; for 0.0833333h; Inert atmosphere; Schlenk technique; Stage #2: diphenyliodonium hexafluorophosphate In acetic acid at 24.84℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique;	99%
Stage #1: indole With Pd2[(C6H4)PPh2]2[O2CC6H5]2; acetic acid at 24.84℃; for 0.0833333h; Inert atmosphere; Schlenk technique; Stage #2: diphenyliodonium hexafluorophosphate at 24.84℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique;	99%

5-methyl-2-pyridone (1003-68-5) + diphenyliodonium hexafluorophosphate (58109-40-3) → Pirfenidone (53179-13-8)

Conditions	Yield
With triethylamine; copper(l) chloride In toluene at 20℃; for 0.5h; Inert atmosphere;	99%

diphenyl sulfide (139-66-2) + diphenyliodonium hexafluorophosphate (58109-40-3) → triphenylsulphonium hexafluorophosphate (57835-99-1)

Conditions	Yield
With copper(II) benzoate In chlorobenzene at 125℃; under 2068.65 Torr; for 0.0333333h; Inert atmosphere; Microwave irradiation;	98%

1,2-diacetoxy-3-butene (18085-02-4) + diphenyliodonium hexafluorophosphate (58109-40-3) → (E)-4-phenylbut-3-ene-1,2-diyl diacetate (119420-99-4)

Conditions	Yield
With palladium diacetate; sodium hydrogencarbonate In acetonitrile at 50℃; for 20h;	98%

1-methylindole (603-76-9) + diphenyliodonium hexafluorophosphate (58109-40-3) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With Pd2[(C6H4)PPh2]2[CF3C(O)CHC(O)CF3]2 In acetic acid at 24.84℃; for 30h; Catalytic behavior; Reagent/catalyst; Time; Solvent; Inert atmosphere; Schlenk technique;	98%
Stage #1: 1-methylindole With Pd2[(C6H4)PPh2]2[O2CC6H5]2; acetic acid at 24.84℃; for 0.0833333h; Inert atmosphere; Schlenk technique; Stage #2: diphenyliodonium hexafluorophosphate at 24.84℃; for 10h; Reagent/catalyst; Inert atmosphere; Schlenk technique;	97%

2-(phenylthio)thioxanthone (1195763-38-2) + potassium trifluorotris(pentafluoroethyl)phosphate (123215-04-3) + diphenyliodonium hexafluorophosphate (58109-40-3) → diphenyl-2-thioxanthonylsulfonium tris(pentafluoroethyl)trifluorophosphate

Conditions	Yield
Stage #1: 2-(phenylthio)thioxanthone; diphenyliodonium hexafluorophosphate With copper(II) benzoate In chlorobenzene at 120 - 125℃; for 3h; Stage #2: potassium tris(pentafluoroethyl)trifluorophosphate In dichloromethane; water at 25℃; for 2h;	98%
Stage #1: 2-(phenylthio)thioxanthone; diphenyliodonium hexafluorophosphate With copper(II) benzoate In chlorobenzene at 120 - 125℃; for 3h; Stage #2: potassium tris(pentafluoroethyl)trifluorophosphate In dichloromethane; water at 25℃; for 2h;
Stage #1: 2-(phenylthio)thioxanthone; diphenyliodonium hexafluorophosphate With copper(II) benzoate In chlorobenzene at 120 - 125℃; for 3h; Stage #2: potassium tris(pentafluoroethyl)trifluorophosphate In dichloromethane; water at 25℃; for 2h;

1-(1H-inden-3-yl)cyclopentan-1-ol + diphenyliodonium hexafluorophosphate (58109-40-3) → 2'-phenyl-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-one

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; C23H22CuF6N2O8S2 In dichloromethane at 0 - 25℃; for 48h; Pinacol Rearrangement; Inert atmosphere; diastereoselective reaction;	98%

1-(1H-inden-3-yl)cyclopentan-1-ol + diphenyliodonium hexafluorophosphate (58109-40-3) → (1S,2'R)-2'-phenyl-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-one

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; [Cu(OTf)2((R)-Ph-BOX)] In dichloromethane at 0 - 25℃; for 48h; Pinacol Rearrangement; Inert atmosphere; stereoselective reaction;	98%

dibenzo-18-crown-6 (14187-32-7) + diphenyliodonium hexafluorophosphate (58109-40-3) → diphenyliodonium hexafluorophosphate-dibenzo-18-crown-6 ether complex

Conditions	Yield
In ethyl acetate for 0.0833333h; Reflux;	97.6%

(E)-(4-(2-(9,9-didecyl-7-nitro-9H-fluoren-2-yl)vinyl)phenyl)(phenyl)sulfane + diphenyliodonium hexafluorophosphate (58109-40-3) → (E)-(4-(2-(9,9-didecyl-7-nitro-9H-fluoren-2-yl)vinyl)phenyl)diphenylsulfonium hexafluorophosphate (V)

Conditions	Yield
With copper(II) benzoate In chlorobenzene at 125℃; under 2068.65 Torr; Inert atmosphere; Microwave irradiation; Darkness;	97%

tris(trifluoromethanesulfonyl)methide potassium salt (114395-69-6) + diphenyliodonium hexafluorophosphate (58109-40-3) → C4F9O6S3(1-)*C12H10I(1+) (182505-78-8)

Conditions	Yield
In ethyl acetate at 20℃; for 1h;	97%

sodium benzenesulfonate (873-55-2) + diphenyliodonium hexafluorophosphate (58109-40-3) → diphenyl sulphone (127-63-9)

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 24h; Schlenk technique; Inert atmosphere;	96%

diphenyliodonium hexafluorophosphate (58109-40-3) + 1-(3,4-dihydro-2H-pyran-6-yl)cyclopentan-1-ol (74938-47-9) → (5R,10R)-10-phenyl-6-oxaspiro[4.5]decan-1-one

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; [Cu(OTf)2((R)-Ph-BOX)] In dichloromethane at 0 - 25℃; for 36h; Pinacol Rearrangement; Inert atmosphere; stereoselective reaction;	96%

1-(5,6-dimethoxy-1H-inden-3-yl)cyclopentan-1-ol + diphenyliodonium hexafluorophosphate (58109-40-3) → 5',6'-dimethoxy-2'-phenyl-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-one

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; C23H22CuF6N2O8S2 In dichloromethane at 0 - 25℃; for 48h; Pinacol Rearrangement; Inert atmosphere; diastereoselective reaction;	96%

1-(5,6-dimethoxy-1H-inden-3-yl)cyclopentan-1-ol + diphenyliodonium hexafluorophosphate (58109-40-3) → (1S,2'R)-5',6'-dimethoxy-2'-phenyl-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-one

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; [Cu(OTf)2((R)-Ph-BOX)] In dichloromethane at 0 - 25℃; for 48h; Pinacol Rearrangement; Inert atmosphere; stereoselective reaction;	96%

(Z)-3-(1-((tert-butyldimethylsilyl)oxy)-5-phenylpent-1-en-1-yl)oxazolidin-2-one (1330660-53-1) + diphenyliodonium hexafluorophosphate (58109-40-3) → (S)-3-(2,5-diphenylpentanoyl)oxazolidin-2-one (1330660-76-8)

Conditions	Yield
With [((CH3)2C(C3H3NOC6H5)2)Cu(OSO2CF3)]; CuOTf*1/2PhMe In dichloromethane; toluene at -10℃; for 24h; optical yield given as %ee; enantioselective reaction;	95%

diphenyliodonium hexafluorophosphate (58109-40-3) + benzonitrile (100-47-0) + phenylpropynoic acid ethyl ester (2216-94-6) → ethyl 2,4-diphenylquinoline-3-carboxylate (17282-90-5)

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 120℃; Inert atmosphere; Sealed tube; regioselective reaction;	95%

diphenyliodonium hexafluorophosphate (58109-40-3) + 6-phenyl-5-hexyne-1-nitrile (152858-50-9) → 9-phenyl-2,3-dihydro-1H-cyclopenta[b]quinoline (10265-82-4)

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 130℃; for 12h; Inert atmosphere; Sealed tube;	95%

(Z)-6-(tert-butyldimethylsilyloxy)-6-(2-oxooxazolidin-3-yl)hex-5-enyl benzoate (1330660-55-3) + diphenyliodonium hexafluorophosphate (58109-40-3) → (S)-6-oxo-6-(2-oxooxazolidin-3-yl)-5-phenylhexyl benzoate (1330660-78-0)

Conditions	Yield
With [((CH3)2C(C3H3NOC6H5)2)Cu(OSO2CF3)]; (CuOTf)2PhMe In dichloromethane; toluene at 0℃; for 24h; optical yield given as %ee; enantioselective reaction;	94%

N-(2-methylbenzoyl)-8-aminoquinoline (1182669-71-1) + diphenyliodonium hexafluorophosphate (58109-40-3) → 2-methyl-N-phenyl-N-(quinolin-8-yl)benzamide

Conditions	Yield
With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h;	94%
With copper(II) acetate monohydrate In 1,2-dichloro-ethane at 80℃; for 48h; Molecular sieve; Schlenk technique;	94%

(Z)-benzyl (6-((tert-butyldimethylsilyl)oxy)-6-(2-oxooxazolidin-3-yl)hex-5-en-1-yl)(methyl)carbamate (1330660-56-4) + diphenyliodonium hexafluorophosphate (58109-40-3) → (S)-benzyl methyl(6-oxo-6-(2-oxooxazolidin-3-yl)-5-phenylhexyl)carbamate (1330660-79-1)

Conditions	Yield
With [((CH3)2C(C3H3NOC6H5)2)Cu(OSO2CF3)]; CuOTf*1/2PhMe In dichloromethane; toluene at 5℃; for 24h; optical yield given as %ee; enantioselective reaction;	93%

N-methylisocarbostyril (4594-71-2) + diphenyliodonium hexafluorophosphate (58109-40-3) → 2-methyl-8-phenylisoquinolin-1(2H)-one

Conditions	Yield
With silver hexafluoroantimonate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In acetic acid at 100℃; for 24h; Mechanism; Reagent/catalyst; Solvent; regiospecific reaction;	93%

ethyl 2-acetoxy-3-butenoate (127700-79-2) + diphenyliodonium hexafluorophosphate (58109-40-3) → (E)-ethyl 2-acetoxy-4-phenylbut-3-enoate (1151782-13-6)

Conditions	Yield
With resorcinolbis[(diphenyl)phosphinite] palladium trifluoroacetate; sodium hydrogencarbonate In acetonitrile at 50℃; for 19h;	92%

3,5-dibromo-2-hydroxypyridine (13472-81-6) + diphenyliodonium hexafluorophosphate (58109-40-3) → 3,5-dibromo-1-phenylpyridin-2(1H)-one (120491-71-6)

Conditions	Yield
With triethylamine; copper(l) chloride In toluene at 20℃; for 0.0833333h; Inert atmosphere;	92%

5-methyl-2-cyanoaniline (26830-96-6) + diphenyliodonium hexafluorophosphate (58109-40-3) → 2-(4-imino-7-methyl-3-phenyl-3,4-dihydroquinazolin-2-yl)-5-methylaniline

Conditions	Yield
In 1,2-dichloro-ethane at 20 - 120℃; for 48h; Inert atmosphere;	92%

diphenyliodonium hexafluorophosphate (58109-40-3) + anthranilic acid nitrile (1885-29-6) → (2-(3-phenyl)-4-imino-3,4-dihydroquinazoline)-2-aniline

Conditions	Yield
In 1,2-dichloro-ethane at 20 - 120℃; for 48h; Inert atmosphere;	92%

methyl 3-(3,4-dihydro-2H-pyran-6-yl)-3-hydroxycyclobutane-1-carboxylate + diphenyliodonium hexafluorophosphate (58109-40-3) → methyl 4-oxo-10-phenyl-6-oxaspiro[4.5]decane-2-carboxylate + methyl 4-oxo-10-phenyl-6-oxaspiro[4.5]decane-2-carboxylate

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; C23H22CuF6N2O8S2 In dichloromethane at 0 - 25℃; for 48h; Pinacol Rearrangement; Inert atmosphere; diastereoselective reaction;	A 92% B 7%

(Z)-3-(1-(tert-butyldimethylsilyloxy)-6-methoxyhex-1-enyl)oxazolidin-2-one (1330660-49-5) + diphenyliodonium hexafluorophosphate (58109-40-3) → (S)-3-(6-methoxy-2-phenylhexanoyl)oxazolidin-2-one (1330660-72-4)

Conditions	Yield
With [((CH3)2C(C3H3NOC6H5)2)Cu(OSO2CF3)]; (CuOTf)2PhMe In dichloromethane; toluene at 0℃; for 24h; optical yield given as %ee; enantioselective reaction;	91%

pyridine N-oxide (694-59-7) + diphenyliodonium hexafluorophosphate (58109-40-3) → 2-(pyridin-1-ium-1-yl)phenolate

Conditions	Yield
Stage #1: pyridine N-oxide; diphenyliodonium hexafluorophosphate In 1,2-dichloro-ethane at 120℃; for 48h; Inert atmosphere; Schlenk technique; Stage #2: With potassium carbonate In methanol; 1,2-dichloro-ethane at 20℃; for 1h;	91%

Upstream product

• 71-43-2 benzene 
• 3109-63-5 tert-butylammonium hexafluorophosphate(V) 
• 591-50-4 iodobenzene 

Downstream Products

• 591-50-4 iodobenzene 
• 92-52-4 biphenyl 
• 103-84-4 Acetanilid 
• 1591-31-7 4-iodo-biphenyl 
• 2113-51-1 2-iodobiphenyl 
• 20442-79-9 3-iodo-1,1'-biphenyl 
• 71-43-2 benzene 
• 82135-89-5 phenylpentamethylenesulfonium hexafluorophosphate 
• 35816-56-9 pentacarbonylmanganate 
• 10170-69-1 dimanganese decacarbonyl 
• 13985-77-8 phenylpentacarbonylmanganese(I) 
• 108-86-1 bromobenzene 
• 591-50-4 phenyliodinium radical cation 
• 14325-34-9 9-ethoxy-9-phenyl-10-anthrone 

Relevant articles and documents

Photoredox-Catalyzed Cascade Reactions Involving Aryl Radical: Total Synthesis of (±)-Norascyronone A and (±)-Eudesmol

Herein, we have developed two types of photoredox-catalyzed cascade reactions using diaryliodonium salts for the concise synthesis of norascyronone A and β-eudesmol. A rationally designed photoredox-catalyzed arylation/cyclization/Friedel-Crafts cascade reaction of enone was exploited to generate the norascyronone polycyclic skeleton. A visible-light-induced radical cyclization/acyloxy-migration reaction was explored to forge the decalin skeleton of eudesmol, and mechanistic studies indicated the reaction was initiated by one-electron oxidation of the enol ester.

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.

Photoinitiators

Halogen onium salts, and onium salts of Group VA and V1A elements having an MF6- anion, where M is selected from P, As and Sb, have been found to exhibit unusual activity under ultraviolet light. These onium salts can be employed as cationic photoinitiators when used with a variety of organic resins and cyclic organic compounds.