N-Iodosuccinimide

• Catalog No.: A14320
• CAS Number: 516-12-1
• M. F.: C4H4INO2
• M. W.: 224.98453
• Purity: 97%

SYNONYMS

• Title: N-碘化丁二酰胺
• IUPAC name: 1-iodopyrrolidine-2,5-dione
• IUPAC Traditional name: N-iodosuccinimide

DATABASE IDS

• MDL Number: MFCD00005512
• CAS Number: 516-12-1
• Merck Index: 145045
• Beilstein Number: 113917
• EC Number: 208-221-6

PROPERTIES

• Purity: 97%
• Density: 2.245
• Melting Point: ca 196°C dec.
• GHS Hazard statements: H301-H315-H319-H335
• European Hazard Symbols: X
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Risk Statements: 22-36/37/38
• RTECS: WN2817000
• Safety Statements: 26-36/37
• Storage Warning: Moisture & Light Sensitive
• TSCA Listed: 否

REFERENCES

• Source of positive iodine. Iodinates methoxy benzenes and naphthalenes in acetonitrile, e.g. anisole gives 95% yield of 4-iodoanisole: Tetrahedron Lett., 37, 4081 (1996).
• In combination with TFA and TFA anhydride, iodinates 2,4-diethoxypyrimidines or N-alkyluracils specifically to their 5-iodo-derivatives: Synth. Commun., 18, 855 (1988). With triflic acid, the "superelectrophile" iodine(I) triflate is formed. This species will iodinate even deactivated aromatics, e.g. nitrobenzene to the m-iodo derivative: J. Org. Chem., 58, 3194 (1993).
• Alone or with a catalytic amount of triflic acid, is a powerful coupling agent in oligosaccharide synthesis, particularly for thioglycosyl donors; see, e.g.: Tetrahedron Lett., 34, 8523 (1993). For reviews, see: Chem. Rev., 93, 1503 (1993); Contemp. Org. Synth., 3, 173 (1996).
• In the presence of triphenylphosphine or triphenyl phosphite, converts alcohols to iodides stereoselectively with inversion: Tetrahedron Lett., 3937 (1973). See also: Carbohydr. Res., 24, 45 (1972).
• In combination with the phase-transfer catalyst, Tetra-n-butylammonium iodide, A15484, oxidizes alcohols to carbonyl compounds in high yield under neutral conditions: Synthesis, 394 (1981). Glycols are cleaved to carbonyl compounds; the rate of reaction is increased by u.v. irradiation: J. Org. Chem., 46, 1927 (1981). Similarly, ɑ-hydroxyacids are oxidatively decarboxylated to ketones: J. Org. Chem., 47, 3006 (1982).
• Oxidative coupling of dianions of acyclic tertiary amides gives a stereoselective preparation of ?-lactams: J. Org. Chem., 57, 1864 (1992):
  
• Has been used in the construction of disulfide bridges in cystine peptides, from cysteine in a DMF-dichloromethane solvent: J. Org. Chem., 58, 3003 (1993).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 960 (2006).
• With K₂CO₃ in MeOH, aldehydes can be oxidized directly to methyl esters: J. Org. Chem., 54, 1213 (1989).