5045. N-Iodosuccinimide

Nomenclature

CAS number: 516-12-1
Succiniodimide; NIS.
C4H4INO2; mol wt 224.98.
C 21.35%, H 1.79%, I 56.41%, N 6.23%, O 14.22%.

Description and references

Prepd by iodination of silver succinimide: Djerassi, Lenk, J. Am. Chem. Soc. 75, 3493 (1953). Structural studies: K. Padmanabhan et al., Acta Crystallogr. C46, 88 (1990). Use as synthetic reagent for cysteine peptides: H. Shih, J. Org. Chem. 58, 3003 (1993); in oxidation and halogenation reactions: A. Speicher, T. Eicher, J. Prakt. Chem. 340, 278 (1998).

Chemical structure

Properties

Needles from dioxane + carbon tetrachloride. mp 200-201°. Sol in acetone, methanol; moderately sol in dioxane. Practically insol in CCl4, ether. Dec in water. Protect from light.

Caution

Avoid contact with skin and mucous membranes.

Use

Iodination of ketones and aldehydes.