N-Iodosuccinimide Chemical Properties

Melting point:

202-206 °C(lit.)

Boiling point:

249.6±23.0 °C(Predicted)

Density 

2,245 g/cm³

storage temp. 

2-8°C

solubility 

Soluble in dioxane, tetrahydrfuran and acetonitrile. Insoluble in ether and carbon tetrachloride.

pka

-2.57±0.20(Predicted)

form 

Crystalline Powder

color 

White-yellow to brown

Water Solubility 

decomposes

Sensitive 

Moisture Sensitive

Merck 

14,5045

BRN 

113917

Stability:

Moisture Sensitive

InChIKey

LQZMLBORDGWNPD-UHFFFAOYSA-N

CAS DataBase Reference

516-12-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

WN2817000

F 

8-9

Hazard Note 

Harmful/Keep Cold/Moisture Sensitive

TSCA 

No

HazardClass 

IRRITANT

HS Code 

29251995

MSDS

• Language:English Provider:1-Iodo-2,5-pyrrolidinedione
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

N-Iodosuccinimide Usage And Synthesis

Chemical Properties

white-yellow to brown crystalline powder

Uses

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.

Uses

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.

Uses

N-Iodosuccinimide is a iodo substituted succinimide that is used 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/ja01110a055
Organic Syntheses, Coll. Vol. 5, p. 663, 1973
Tetrahedron 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.]

N-Iodosuccinimide(516-12-1)Related Product Information

• Succinimide
• Dispersing agent 155
• N-Bromosuccinimide
• N-Hydroxysuccinimide
• O-Phthalimide
• N-Chlorosuccinimide
• Diethyl succinosuccinate
• Bismaleimide
• Sodium thiosulfate pentahydrate
• Taurine
• 1H-Benzotriazole
• Meglumine
• Sulfamic acid
• N-Fluorobenzenesulfonimide
• 2-Methylaminoethanol
• Mepiquat chloride
• N-Carbobenzyloxy-D-asparagine
• N-Phenyl-bis(trifluoromethanesulfonimide)