DIPHENYLIODONIUM TRIFLUOROMETHANESULFONATE

DIPHENYLIODONIUM TRIFLUOROMETHANESULFONATE Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

DIPHENYLIODONIUM TRIFLUOROMETHANESULFONATE Chemical Properties,Usage,Production

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