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N-Iodosuccinimide

Catalog No. A14320 Name Alfa Aesar
CAS Number 516-12-1 Website
M. F. C4H4INO2 Telephone
M. W. 224.98453 Fax
Purity 97% Email
Storage Chembase ID: 22338

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 Pictograms GHS06
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

DETAILS

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).