N-Iodosuccinimide NEW

N-Iodosuccinimide

Product Name N-Iodosuccinimide

CAS 516-12-1

MF C4H4INO2

MW 224.98

EINECS 208-221-6

MOL File 516-12-1.mol

Chemical Properties

Melting point 202-206 °C(lit.)
Boiling point 249.6±23.0 °C(Predicted)
Density  2,245 g/cm3
storage temp.  2-8°C
solubility  Soluble in dioxanee, tetrahydrfuran and acetonitrilee. Insoluble in ether and carbon tetrachloridee.
form  Crystalline Powder
pka -2.57±0.20(Predicted)
color  White-yellow to brown
Water Solubility  decomposes
Sensitive  Moisture Sensitive

Usage And Synthesis
Chemical Properties

white-yellow to brown crystalline powder

Uses

N-Iodosuccinimide is a iodo substituted succinimide that is used as an iodinating agent in chemical synthesis.

Uses

Iodination of ketones and aldehydes.
Highly substituted iodobenzenes prepared via an efficient 2-step process from 1,6-diynes.
Used with TFA to chemoselectively hydrolyze thioglycosides to 1-hydroxyglycosides.
Synthesis of vinyl sulfones from olefins and benzenesulfinic acid.

Uses

N-Iodosuccinimide is used in the preparation of vinyl sulfones from olefins and benzenesulfinic acid. It acts as a source for I+ and involved in Hunsdiecker reactions for the conversion of cinnamic acids, and propiolic acids to the corresponding alfa-halostyrenes and 1-halo-1-alkynes respectively. It is also used to hydrolyze thioglycosides to 1-hydroxyglycosides with triluoroacetic acid. It is involved in the preparation of iodobenzene from 1,6-diynes. Further, it acts as an iodinating agent in chemical synthesis.

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