N-Iodosaccharin
Title: N-Iodosaccharin
CAS Registry Number: 86340-94-5
CAS Name: 2-Iodo-1,2-benzisothiazol-3(2H)-one 1,1-dioxide
Additional Names: NISac
Molecular Formula: C7H4INO3S
Molecular Weight: 309.08
Percent Composition: C 27.20%, H 1.30%, I 41.06%, N 4.53%, O 15.53%, S 10.37%
Literature 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).
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.
Melting point: mp 206-208°
pKa: pKa: 1.30
Use: Iodination reagent; activator of thioglycosides.

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