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N-Iodosuccinimide

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N-Iodosuccinimide Basic information

Product Name:
N-Iodosuccinimide
Synonyms:
  • 1-iodo-5-pyrrolidinedione
  • 1-IODO-2,5-PYRROLIDINEDIONE
  • NIS
  • N-IODOSUCCINIMIDE
  • N-Iodosuccinimide, 98+%
  • N-Iodosuccinimide ,99%
  • N-Iodosuccinimide , (1-Iodo-2,5-pyrrolidinedione)
  • 1-Iodopyrrolidine-2,5-dione, 2,5-Dioxo-1-iodopyrrolidine
CAS:
516-12-1
MF:
C4H4INO2
MW:
224.98
EINECS:
208-221-6
Product Categories:
  • C-X Bond Formation (Halogen)
  • Synthetic Reagents
  • Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
  • API intermediates
  • Biochemistry
  • Halogenation
  • Iodination
  • N-Substituted Maleimides, Succinimides & Phthalimides
  • N-Substituted Succinimides
  • Reagents for Oligosaccharide Synthesis
  • Synthetic Organic Chemistry
  • 516-12-1
  • bc0001
Mol File:
516-12-1.mol
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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)
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Safety Information

Hazard Codes 
Xn,Xi
Risk Statements 
22-36/37/38
Safety Statements 
26-36-37/39
WGK Germany 
3
RTECS 
WN2817000
8-9
Hazard Note 
Harmful/Keep Cold/Moisture Sensitive
TSCA 
No
HazardClass 
IRRITANT
HS Code 
29251995

MSDS

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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 Preparation Products And Raw materials

Preparation Products

Raw materials

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