Consentement d'utilisation des Cookies

J'accepte. Notre site sauvegarde des traceurs textes (cookies) sur votre appareil afin de vous garantir de meilleurs contenus et à des fins de collectes statistiques.Vous pouvez désactiver l'usage des cookies en changeant les paramètres de votre navigateur. En poursuivant votre navigation sur notre site sans changer vos paramètres de navigateur vous nous accordez la permission de conserver des informations sur votre appareil.

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

A14320 N-Iodosuccinimide, 97%

Numéro de CAS
516-12-1
Synonymes

Conditionnement Prix ($) Quantité Disponibilité
5g 42,70
25g 150,00
100g 454,00
Ajouter au panier Ajouter au devis en vrac Afficher l'article

N-Iodosuccinimide, 97%

MDL
MFCD00005512
EINECS
208-221-6

Propriétés chimiques

Formule
C4H4INO2
Poids moleculaire
224.99
Point de fusion
ca 196° dec.
Densité
2.245
Sensibilité
Moisture & Light Sensitive
Solubilité
Soluble in dioxane, tetrahydrfuran and acetonitrile. Insoluble in ether and carbon tetrachloride.

Applications

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.

Notes

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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H302-H315-H319-H335

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

Mentions de prudence: P261-P280a-P305+P351+P338-P304+P340-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Merck
14,5045
Beilstein
113917
Code tarifaire harmonisé
2925.19
TSCA
No
RTECS
WN2817000

Recommandé

Consulté récemment

Produits chimiques

Sciences de la vie

Métaux et matériaux

Catalyseurs

Analytique et matériel de laboratoire