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N-Iodosuccinimide

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N-Iodosuccinimide
Names
Preferred IUPAC name 1-Iodopyrrolidine-2,5-dione
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 113917
ChEBI
ChemSpider
ECHA InfoCard 100.007.475 Edit this at Wikidata
EC Number
  • 208-221-6
Gmelin Reference 122896
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H4INO2/c5-6-3(7)1-2-4(6)8/h1-2H2Key: LQZMLBORDGWNPD-UHFFFAOYSA-N
SMILES
  • C1CC(=O)N(C1=O)I
Properties
Chemical formula C4H4INO2
Molar mass 224.985 g·mol
Appearance White solid
Density 2.245 g/cm
Melting point 202–206 °C (396–403 °F; 475–479 K)(dec.)
Solubility dioxane, THF, MeCN; insoluble in ether, CCl4
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H315, H319, H335
Precautionary statements P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

N-Iodosuccinimide (NIS) is a reagent used in organic chemistry for the iodination of alkenes and as a mild oxidant.

NIS is the iodine analog of N-chlorosuccinimide (NCS) and N-bromosuccinimide (NBS) which are used for similar applications.

References

  1. "N-Iodosuccinimide". Sigma-Aldrich.
  2. Scott C. Virgil; Zeng, Ying; Kong, Fanzuo; Pigza, Julie A. (2001). "N-Iodosuccinimide". E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.ri038.pub3. ISBN 0471936235.
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