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N-Iodosuccinimide

N-Iodosuccinimide Structure
N-Iodosuccinimide structure
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-IODOSUCCINIMIDE;n-iodo-succinimid;N-lodosuccinimide
CBNumber:
CB0342078
Molecular Formula:
C4H4INO2
Molecular Weight:
224.98
MDL Number:
MFCD00005512
MOL File:
516-12-1.mol
MSDS File:
SDS
Last updated:2024-11-27 17:31:30
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N-Iodosuccinimide 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.
form Crystalline Powder
pka -2.57±0.20(Predicted)
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)
FDA UNII 3COS3X3N4P

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08,GHS09
Signal word  Warning
Hazard statements  H315-H317-H319-H341-H410
Precautionary statements  P201-P273-P280-P302+P352-P305+P351+P338-P308+P313
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
NFPA 704
1
2 0

N-Iodosuccinimide price More Price(54)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 220051 N-Iodosuccinimide 95% 516-12-1 5g $58.9 2024-03-01 Buy
Sigma-Aldrich 220051 N-Iodosuccinimide 95% 516-12-1 25g $126 2024-03-01 Buy
TCI Chemical I0074 N-Iodosuccinimide >98.0%(T) 516-12-1 5g $47 2024-03-01 Buy
TCI Chemical I0074 N-Iodosuccinimide >98.0%(T) 516-12-1 25g $134 2024-03-01 Buy
Alfa Aesar A14320 N-Iodosuccinimide, 97% 516-12-1 5g $53.1 2024-03-01 Buy
Product number Packaging Price Buy
220051 5g $58.9 Buy
220051 25g $126 Buy
I0074 5g $47 Buy
I0074 25g $134 Buy
A14320 5g $53.1 Buy

N-Iodosuccinimide Chemical Properties,Uses,Production

Chemical Properties

white-yellow to brown crystalline powder

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.

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.

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 synthesis

123-56-8
516-12-1
Synthesis of N-Iodosuccinimide from Succinimide

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 3-b]pyridine DBCO-NHS Ester
5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine Iodoferrocene 2-Amino-5-fluoro-3-iodo-benzoic acid methyl ester 2(1H)-Pyridinone, 6-amino-3-iodo-5-nitro-

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N-Iodosuccinimide Suppliers

Global( 640)Suppliers
Supplier Tel Email Country ProdList Advantage
Wuhu Nuowei chemistry Co., Ltd.
+86-0553-2911116-802 +undefined17756524438 sales1@nuowei-chem.com China 1638 58
LEAP CHEM CO., LTD.
+86-852-30606658 market18@leapchem.com China 24727 58
Jinan Dexinjia Bio&Tech Co., Ltd
+86-0531-82375893 +86-15064117275 sales@jndxj.com China 1267 58
Hebei Fengmu Trading Co., Ltd.
+8613393234347 Lyla@fengmuchem.com China 2946 58
Hebei Weibang Biotechnology Co., Ltd 		+8615531157085 abby@weibangbio.com China 8807 58
Hebei Mojin Biotechnology Co., Ltd 		+86 13288715578 +8613288715578 sales@hbmojin.com China 12834 58
Hebei Chuanghai Biotechnology Co,.LTD 		+86-13131129325 sales1@chuanghaibio.com China 5889 58
Hebei Weibang Biotechnology Co., Ltd 		+8617732866630 bess@weibangbio.com China 18151 58
Hebei Jingbo New Material Technology Co., Ltd 		+8619931165850 hbjbtech@163.com China 1000 58
airuikechemical co., ltd. 		+86-18353166132 +86-18353166132 sales02@airuikechemical.com China 983 58
Supplier Advantage
Wuhu Nuowei chemistry Co., Ltd.
58
LEAP CHEM CO., LTD.
58
Jinan Dexinjia Bio&Tech Co., Ltd
58
Hebei Fengmu Trading Co., Ltd.
58
Hebei Weibang Biotechnology Co., Ltd 		58
Hebei Mojin Biotechnology Co., Ltd 		58
Hebei Chuanghai Biotechnology Co,.LTD 		58
Hebei Weibang Biotechnology Co., Ltd 		58
Hebei Jingbo New Material Technology Co., Ltd 		58
airuikechemical co., ltd. 		58

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View Lastest Price from N-Iodosuccinimide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
N-Iodosuccinimide pictures 2024-12-26 N-Iodosuccinimide
516-12-1
 US $10.00 / kg 1kg 99% 20ton Hebei Zhuanglai Chemical Trading Co.,Ltd
N-Iodosuccinimide pictures 2024-12-26 N-Iodosuccinimide
516-12-1
 US $6.00 / kg 1kg 99% 2000KG/Month HebeiShuoshengImportandExportco.,Ltd
N-Iodosuccinimide pictures 2024-12-24 N-Iodosuccinimide
516-12-1
 US $0.00-0.00 / g 1g 99.99% 20 tons airuikechemical co., ltd.

N-Iodosuccinimide Spectrum

N-Iodosuccinimide(516-12-1)1HNMRN-Iodosuccinimide(516-12-1)13CNMRN-Iodosuccinimide(516-12-1)IR1N-Iodosuccinimide(516-12-1)IR2N-Iodosuccinimide(516-12-1)Raman

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