5043. N-Iodosaccharin

Nomenclature

CAS number: 86340-94-5
2-Iodo-1,2-benzisothiazol-3(2H)-one 1,1-dioxide; NISac.
C7H4INO3S; mol wt 309.08.
C 27.20%, H 1.30%, I 41.06%, N 4.53%, O 15.53%, S 10.37%.

Description and references

Iodination reagent. Prepn: M. Papadopoulou, A. Varvoglis, J. Chem. Res. Synop. 1983, 66. Synthesis and use for iodination of aromatics and alkenes: D. Dolenc, Synlett 2000, 544. As an activator of thioglycosides: M. Aloui, A. J. Fairbanks, ibid. 2001, 797; eidem, Chem. Commun. 2001, 1406. Iodination of enol acetates and diones: D. Dolenc, Synth. Commun. 33, 2917 (2003); of isatins: S. P. L. de Souza et al., Heterocycl. Commun. 9, 31 (2003).

Chemical structure

Properties

Crystallizes in small pale yellow crystals as the monohydrate, mp 206-208°. Reprecipitation from THF , then drying produces a white powder which can be stored indefinitely in a dark freezer. pKa: 1.30. Sol in common organic solvents (better in more polar ones such as acetone, acetonitrile). Insol in water.

Use

Iodination reagent; activator of thioglycosides.