Chemical properties and uses of N-Iodosuccinimide

                               Chemical properties and uses of N-Iodosuccinimide

Chemical properties

N-iodosuccinimide, commonly abbreviated as NIS, is a white needle-shaped crystal. The 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. NIS is an important electrophilic iodination reagent in organic chemistry. It can react with alkenyl aluminum intermediates to prepare alkenyl iodide compounds. It can also be used as an oxidizing reagent to oxidize and cyclize dipeptides to prepare β-lactams. NIS is a good iodination reagent that can smoothly convert vinyl silane and vinyl stannane into the corresponding vinyl iodide. In addition, under mild conditions, olefin boronic acid reacts with NIS to convert into olefin iodide with unchanged geometric configuration. NIS is easy to decompose and should be stored at low temperature, away from light and moisture under nitrogen protection. When using it, you should take necessary measures to prevent inhalation of powder with pungent odor.

uses

1. Used in organic synthesis, sulfur oxidation titration reagent, mild iodination agent, glucosinolate catalyst, etc.

2. Used for chemically selective hydrolysis of mustard oil glycosides with TFA to generate 1-hydroxyglycosides; prepare highly substituted iodobenzenes through an effective 2-step process via 1,6-diyne; synthesize vinyl sulfone by reaction of olefins with benzenesulfinic acid.

3. Mainly used as a pharmaceutical intermediate in biopharmaceuticals. N-iodosuccinimide is used as an iodination agent in chemical synthesis.