NIS (N-Iodosuccinimide)

Technical Specifications

Product Description & Scientific Applications

N-Iodosuccinimide, NIS (C4H4INO2, 224.98 g/mol), is the N-iodo imide of succinimide. It belongs to the N-halosuccinimide class of mild, selective electrophilic halogenating reagents, alongside the chloro and bromo analogues.

Applications and Reactions

• Heteroarene iodination: NIS attacks the most nucleophilic ring position, so electron-rich heteroarenes iodinate directly without a catalyst. On ethyl imidazole-4-carboxylate it installs two iodines in one operation, 93% yield, giving a doubly halogenated coupling partner. With pyridinium p-toluenesulfonate it becomes site-selective, functionalising the C5 and C5′ positions of a symmetric intermediate in 88% without protecting the rest of the scaffold.
• Glycosylation: with triflic acid it activates thioglycoside donors, giving glycosylation in 89% yield with α selectivity. The same NIS/TfOH activation drives automated thioglycoside couplings under a controlled temperature profile from −20 to 0 °C.
• Iodocyclisation: closes a cycloisomerisation substrate in 85% yield, delivering the iodinated ring system ready for cross-coupling.
• Halogen-bond donors: converts arenes into halogen-bond donors in a single smooth step.
• Chalcogenation: as a catalytic iodine source it enables seleno- and thiocyanation of electron-rich arenes such as indoles.
• Limitations: it is not always the best iodine source. In one indole coupling it gave 40% under conditions where molecular iodine performed better.
• Storage: 2–8 °C in a tightly sealed container, protected from light and moisture.

Shipping Destinations

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