ChemicalBook > CAS DataBase List > N-Iodosuccinimide

N-Iodosuccinimide

Product Name
N-Iodosuccinimide
CAS No.
516-12-1
Chemical Name
N-Iodosuccinimide
Synonyms
NIS;1-iodopyrrolidine-2,5-dione;Iodosuccinimide;N-IodosucciniMide (NIS);1-IODO-2,5-PYRROLIDINEDIONE;N-iododiimide;succiniodimide;N-Iodouccinimide;N-IODOSUCCINIMIDE;n-iodo-succinimid
CBNumber
CB0342078
Molecular Formula
C4H4INO2
Formula Weight
224.98
MOL File
516-12-1.mol
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N-Iodosuccinimide Property

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

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H341Suspected of causing genetic defects

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
220051
Product name
N-Iodosuccinimide
Purity
95%
Packaging
5g
Price
$60.7
Updated
2025/07/31
Sigma-Aldrich
Product number
220051
Product name
N-Iodosuccinimide
Purity
95%
Packaging
25g
Price
$130
Updated
2025/07/31
TCI Chemical
Product number
I0074
Product name
N-Iodosuccinimide
Purity
>98.0%(T)
Packaging
5g
Price
$47
Updated
2025/07/31
TCI Chemical
Product number
I0074
Product name
N-Iodosuccinimide
Purity
>98.0%(T)
Packaging
25g
Price
$134
Updated
2025/07/31
Sigma-Aldrich
Product number
220051
Product name
N-Iodosuccinimide
Purity
95%
Packaging
100g
Price
$482
Updated
2025/07/31
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N-Iodosuccinimide Chemical Properties,Usage,Production

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

Synthesis

123-56-8

516-12-1

The general procedure for synthesizing N-iodosuccinimide from succinimide was as follows: a mixture of succinimide (1.0 g, 10.1 mmol), iodobenzene diacetate (1.95 g, 6.06 mmol), iodine (1.67 g, 6.57 mmol), and benzene (20 mL) was stirred and reacted for 15 hours at room temperature. Subsequently, the reaction mixture was cooled and kept at 0 to 5 °C for 1 hour. The precipitated solid product was filtered, the filter cake was washed with cold benzene and finally dried under vacuum to give 2.2 g of N-iodosuccinimide in 99% yield.

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.]

References

[1] Patent: WO2015/68159, 2015, A2. Location in patent: Paragraph 00171-00172
[2] Journal of Organometallic Chemistry, 1983, vol. 255, # 3, p. 295 - 298

N-Iodosuccinimide Preparation Products And Raw materials

Raw materials

Diimine Succinimide 1,4-Dioxane

Preparation Products

2-Chloro-4-nitrophenyl-alpha-L-fucopyranoside 3-Iodo-4,5-dimethoxybenzaldehyde 5-Iodo-2,4-dimethoxypyrimidine
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View Lastest Price from N-Iodosuccinimide manufacturers

Hebei Chuanghai Biotechnology Co., Ltd
Product
N-Iodosuccinimide 516-12-1
Price
US $9.90/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-27
HebeiShuoshengImportandExportco.,Ltd
Product
N-Iodosuccinimide 516-12-1
Price
US $6.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
2000KG/Month
Release date
2024-08-05
Hebei Chuanghai Biotechnology Co., Ltd
Product
N-Iodosuccinimide 516-12-1
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-10-31

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  • 516-12-1
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  • C4H4INO2
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