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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.
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).
With K2CO3 in MeOH, aldehydes can be oxidized directly to methyl esters: J. Org. Chem., 54, 1213 (1989).
Oxidative coupling of dianions of acyclic tertiary amides gives a stereoselective preparation of ß-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).
Zhang, J.; Zhang, X.; Wu, W.; Zhang, G.; Xu, S.; Shi, M. Intramolecular aminochalcogenation and diamination of alkenes employing N-iodosuccinimide. Tetrahedron Lett. 2015, 56 (12), 1505-1509.
Kimura, T.; Takahashi, D.; Toshima, K. Glycosylations of Glycals using N-Iodosuccinimide (NIS) and Phosphorus Compounds for Syntheses of 2-Iodo-and 2-Deoxyglycosides. J. Org. Chem. 2015, 80 (19), 9552-9562.
Hazard Statements: H302-H315-H319-H335-H500
Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. May form combustible dust concentrations in air
Precautionary Statements: P261-P264b-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant