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516-12-1 - N-Iodosuccinimide, 97% - A14320 - Alfa Aesar

A14320 N-Iodosuccinimide, 97%

CAS Number

Size Price ($) Quantity Availability
5g 42.54
25g 144.14
100g 434.03
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N-Iodosuccinimide, 97%


Chemical Properties

Formula Weight
Melting point
ca 196° dec.
Moisture & Light Sensitive
Soluble in dioxane, tetrahydrfuran and acetonitrile. Insoluble in ether and carbon tetrachloride.


N-Iodosuccinimide is used in the preparation of vinyl sulfones from olefins and benzenesulfinic acid. It acts as a source for I<sup>+</sup> 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.


Moisture and light sensitive. Store in a cool place. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents and strong bases.

Literature 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).

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H315-H319-H335

Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P301+P312-P312-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

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