Bis(4-tert-butylphenyl)iodonium perfluoro-1-butanesulfonate Chemical Properties

Melting point:

175-177 °C (lit.)

solubility 

PGMEA: ~40%

InChI

InChI=1S/C20H26I.C4HF9O3S/c1-19(2,3)15-7-11-17(12-8-15)21-18-13-9-16(10-14-18)20(4,5)6;5-1(6,3(9,10)11)2(7,8)4(12,13)17(14,15)16/h7-14H,1-6H3;(H,14,15,16)/q+1;/p-1

InChIKey

DJBAOXYQCAKLPH-UHFFFAOYSA-M

SMILES

C(C(F)(F)C(F)(F)F)(F)(F)C(F)(F)S([O-])(=O)=O.C1(C(C)(C)C)=CC=C([I+]C2=CC=C(C(C)(C)C)C=C2)C=C1

EPA Substance Registry System

Bis(4-tert-butylphenyl)iodanium nonafluorobutane-1-sulfonate (194999-85-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

Bis(4-tert-butylphenyl)iodonium perfluoro-1-butanesulfonate Usage And Synthesis

Uses

Cationic photoinitiator. Photoacid generator.

Research

To test the reactivity of gaseous 18F-AcF in radiofluorination, bis(4-tert-butylphenyl)iodonium perfluoro-1-butanesulfonate was radiofluorinated with anhydrous 18F-CsF (generated from 18F-AcF and 20 mg Cs2CO3) in 0.3 mL anisole. The results supported the high reactivity for 18F-fluoride derived from 18F-AcF [1].    Bis(4-tert-butylphenyl)iodonium perfluoro-1-butanesulfonate is a photoinitiator (PI). The photoinitiator (PI) mechanisms are radical and cationic. In the cationic PI system, light is absorbed, causing heterolytic and homolytic cleavage that forms a cationic portion (labeled in green) and anionic portion (labeled in pink). The generated molecules are reactive with monomers, forming an acid and free radicals, propagating polymerization[2].    

References

[1] Huailei Jiang , Timothy R. DeGrado, Stephen G. DiMagno . “Production and transport of gaseous 18F-synthons: 18F-acyl fluorides.” Journal of Fluorine Chemistry 180 (2015): Pages 181-185.
[2] Megan Carve, &Donald Wlodkowic. “3D-Printed Chips: Compatibility of Additive Manufacturing Photopolymeric Substrata with Biological Applications.” Micromachines 9 2 (2018).

Bis(4-tert-butylphenyl)iodonium perfluoro-1-butanesulfonate(194999-85-4)Related Product Information

• Nonafluorobutane-1-sulfonic acid
• 3,3,4,4,5,5,5-HEPTAFLUOROPENTANOIC ACID
• 1-tert-butyl-4-iodobenzene
• Bis(4-tert-butylphenyl)iodonium perfluoro-1-butanesulfonate
• NONAFLUOROPENTANAL HYDRATE
• PERFLUOROPENTANOIC ACID