DIPHENYLIODONIUM TRIFLUOROMETHANESULFONATE Chemical Properties

Melting point:

180-181 °C (lit.)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

PGMEA: ~1%

form 

Crystalline Powder

color 

White to slightly yellow

Sensitive 

Light Sensitive

BRN 

3582403

InChI

InChI=1S/C12H10I.CHF3O3S/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;2-1(3,4)8(5,6)7/h1-10H;(H,5,6,7)/q+1;/p-1

InChIKey

SBQIJPBUMNWUKN-UHFFFAOYSA-M

SMILES

C1(C=CC=CC=1)[I+]C1=CC=CC=C1.C(F)(F)(F)S([O-])(=O)=O

CAS DataBase Reference

66003-76-7(CAS DataBase Reference)

EPA Substance Registry System

Iodonium, diphenyl-, 1,1,1-trifluoromethanesulfonate (1:1) (66003-76-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

8-10

Hazard Note 

Irritant

HazardClass 

6.1

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

DIPHENYLIODONIUM TRIFLUOROMETHANESULFONATE Usage And Synthesis

Uses

Diphenyliodonium Trifluoromethanesulfonate is a useful research chemical.

Uses

Reagent for phenylation.

Uses

Cationic photoinitiator. Photoacid generator.

Synthesis

5.5 mmol of m-chloroperoxybenzoic acid as an oxidizing agent was added to the reaction flask along with 5.5 mmol of iodobenzene, 15 mL of dichloromethane, 5 mmol of benzene, 10 mmol of trifluoromethanesulfonic acid, and a stirrer, and a condensation tube was installed to condense the reaction from the bottom to the top at room temperature. Subsequently, the reaction flask was heated in an oil bath at 40 °C for the condensation reflux reaction. The reaction was continued under magnetic stirring for 1 hour. Upon completion of the reaction, the reaction solution was rotary dried using a rotary evaporator (40 °C water bath). To the dried product, 20 mL of ether was added and stirred at room temperature for 30 min, after which the mixture was cooled in a 0-4 °C medical refrigerator for 15 min. After removal, the mixture was withdrawn and filtered through a Büchner funnel using ether as eluent. The solid product on the filter paper was collected and dried in an oven at 100 °C for 24 h. Diaryl iodonium trifluoromethanesulfonate was finally obtained in 88% yield. During rotary drying, the control conditions were 0.1 MPa and 40 °C.

References

[1] Organic Letters, 2011, vol. 13, # 13, p. 3462 - 3465
[2] Chemistry--A European Journal, 2012, vol. 18, # 44, p. 14140 - 14149,10
[3] Organic Letters, 2015, vol. 17, # 18, p. 4554 - 4557
[4] Organic Letters, 2015, vol. 17, # 11, p. 2688 - 2691
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 31, p. 8928 - 8932

DIPHENYLIODONIUM TRIFLUOROMETHANESULFONATE(66003-76-7)Related Product Information

• Diphenylacetyl chloride
• O-Diphenylphosphinylhydroxylamine
• Diphenyl(trimethylsilyl)phosphine
• Perfluoro-1-iodohexane
• Perfluorobutyl iodide
• Scandium trifluoromethanesulfonate
• FLUOROSULFONIC ACID
• Dess-Martin periodinane
• Trifluoromethanesulfonic acid
• DIPHENYLIODONIUM IODIDE
• (4-METHOXYPHENYL)PHENYLIODONIUM TRIFLATE
• DIPHENYLIODONIUM TRIFLUOROMETHANESULFONATE
• PHENYL[2-(TRIMETHYLSILYL)PHENYL]IODONIUM TRIFLATE
• BIS(4-TERT-BUTYLPHENYL)IODONIUM TRIFLATE
• Trifluoromethane