516-12-1 Usage
Chemical Properties
white-yellow to brown crystalline powder
Uses
Different sources of media describe the Uses of 516-12-1 differently. You can refer to the following data:
1. N-Iodosuccinimide is a iodo substituted succinimide that is used as an iodinating agent in chemical synthesis.
2. Iodination of ketones and aldehydes.
Highly substituted iodobenzenes prepared via an efficient 2-step process from 1,6-diynes.
Used with TFA to chemoselectively hydrolyze thioglycosides to 1-hydroxyglycosides.
Synthesis of vinyl sulfones from olefins and benzenesulfinic acid.
3. 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.
Preparation
To a solution of 39.2g of succinimide in 1200ml of boiling water was added 51.0g of freshly precipitated silver oxide, the mixture was filtered and the silver salt was allowed to crystallize. Filtration and washing with cold water furnished 45.0g of the silver salt of succinimide suitable for the iodination step.
The finely powdered salt (49.5g) was added in portions with stirring to a solution of 50.8g of iodine in 300ml of acetone, the temperature being maintained at 5-10°C. After decolorization (30 min.), the silver iodide was filtered, the solvent was removed under reduced pressure at room temperature and the residue was washed with ether, yielding 43g of N-iodosuccinimide with mp 189-191°C. An analytical sample (85% recovery) was obtained by dissolving in the minimum quantity of hot dioxane and precipitating with carbon tetrachloride; colorless needles, mp 200-201°C.
Ref: JACS 75, 3493 (1953)
Definition
ChEBI: N-iodosuccinimide is a five-membered cyclic dicarboximide compound having an iodo substituent on the nitrogen atom. It is a dicarboximide and a pyrrolidinone. It derives from a succinimide.
Reactions
N-Iodosuccinimide (NIS) is an iodinating agent that is used for various electrophilic iodinations and as source for iodine in radical reactions.
N-Iodosuccinimide is the least reactive of the N-haloamides in aromatic substitution. N-Iodosuccinimide does not act as an iodinating agent in pure dimethyl sulfoxide or N-ethylacetamide. On the other hand, butyl disulfide and a number of other sulfur-containing compounds are effective catalysts at low concentration for the iodination of guanosine derivatives using N-iodosuccinimide. This catalytic effect is observed when dimethyl sulfoxide is used as the solvent,but not when N-ethylacetamide is used.
https://www.organic-chemistry.org/chemicals/oxidations/n-iodosuccinimide-nis.shtm
Synthesis Reference(s)
Journal of the American Chemical Society, 75, p. 3493, 1953 DOI: 10.1021/ja01110a055Organic Syntheses, Coll. Vol. 5, p. 663, 1973Tetrahedron Letters, 25, p. 233, 1984 DOI: 10.1016/S0040-4039(00)99848-4
Purification Methods
Crystallise it from dioxane/CCl4. It iodinates arenes in triflic acid. [Olah et al J Org Chem 58 3194 1993, Beilstein 21/9 V 544.]
Check Digit Verification of cas no
The CAS Registry Mumber 516-12-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 6 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 516-12:
(5*5)+(4*1)+(3*6)+(2*1)+(1*2)=51
51 % 10 = 1
So 516-12-1 is a valid CAS Registry Number.
InChI:InChI=1/C4H4INO2/c5-6-3(7)1-2-4(6)8/h1-2H2
516-12-1Relevant articles and documents
Synthesis of N-iodosuccinimide and its application in H2SO4 as efficient iodination reagent for deactivated aromatic compounds
Chaikovskii,Skorokhodov,Filimonov
, p. 1503 - 1504 (2001)
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Electrophilic Substitution of Hydrogen in Betulin and Diacetylbetulin
Bodrikov,Kurskii, Yu. A.,Chiyanov,Subbotin, A. Yu.
, p. 131 - 138 (2018/06/14)
Betulin and diacetylbetulin, which can be regarded as sterically hindered alkenes, reacted with N-chloro-, N-bromo-, and N-iodosuccinimides to give products of allylic and vinylic substitution in quantitative overall yield. The contribution of allylic substitution increases in the series Cl Br I. Quantum chemical simulation of the reactions of diacetylbetulin with N-halosuccinimides showed that, regardless of the electrophile power, all reactions involve open-chain carbocationic intermediates. The direction of deprotonation of the latter with formation of allylic or vinylic substitution products is determined by preferential orientation of the vacant orbital and C–Hlg bond.
Glycosylation with Disarmed Glycosyl Bromides Promoted by Iodonium Ions
Lanz, Gyrithe,Madsen, Robert
supporting information, p. 3119 - 3125 (2016/07/12)
Iodonium ions have been developed for activating glycosyl bromides in the coupling to glycosyl acceptors. The iodonium ions are generated from N-iodosuccinimide and a protic acid such as camphorsulfonic acid or triflic acid, where the latter gives the most reactive promoter system. The couplings occur with the release of iodine monobromide, and the best results are obtained with benzoylated glycosyl donors and acceptors. In this way, disarmed glycosyl bromides can serve as glycosyl donors without the use of heavy-metal salts.
