N-Iodosuccinimide

N-Iodosuccinimide (NIS) is a reagent used in organic chemistry for the iodination of alkenes and as a mild oxidant.[2][3]

N-Iodosuccinimide
Iodosuccinimide.svg
Names
Preferred IUPAC name
1-Iodopyrrolidine-2,5-dione
Identifiers
3D model (JSmol)
113917
ChEBI
ChemSpider
ECHA InfoCard 100.007.475 Edit this at Wikidata
EC Number
  • 208-221-6
122896
UNII
  • InChI=1S/C4H4INO2/c5-6-3(7)1-2-4(6)8/h1-2H2
    Key: LQZMLBORDGWNPD-UHFFFAOYSA-N
  • C1CC(=O)N(C1=O)I
Properties
C4H4INO2
Molar mass 224.985 g·mol−1
Appearance White solid
Density 2.245 g/cm3
Melting point 202–206 °C (396–403 °F; 475–479 K)(dec.) [1]
Soluble in Dioxane, THF, MeCN; Insoluble in ether, CCl4
Hazards
GHS pictograms GHS07: Harmful
GHS Signal word Warning
H302, H315, H319, H335
P261, P264, P270, P271, P280, P301+312, P302+352, P304+340, P305+351+338, P312, P321, P330, P332+313, P337+313, P362, P403+233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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

ReferencesEdit

  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.
  3. ^ "N-Iodosuccinimide - Huateng Pharma".