N-Iodosuccinimide: A Versatile Reagent in Synthetic Chemistry

N-iodosuccinimide, commonly abbreviated as NIS, is a white needle-shaped crystal. Melting point is 200-201°C. It is soluble in acetone and methanol, slightly soluble in dioxane, and almost insoluble in carbon tetrachloride and ether. It decomposes in water. It can be prepared in the laboratory by reacting N-succinimide silver salt with iodine.

Synthesis of N-Iodosuccinimide

N-Iodosuccinimide is prepared by reacting of N-silversuccinimide with I2 in anhydrous dioxane, removal of AgI by fitration, and addition of CCl4 to promote crystallization.1

Purification

Recrystallization from dioxane–CCl4 at −20 °C.

Applications of N-Iodosuccinimide

N-Iodosuccinimide reacts with enol acetates derived from ketones to give α-iodoketones, and the reaction has found application in the steroid field.The iodination of the enol acetates seems to proceed by an ionic mechanism, and preliminary work indicates that N-iodosuccinimide is not capable of at least some of the radical-chain iodinations analogous to radical-chain brominations brought about by N-bromosuccinimide.

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