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220051

Sigma-Aldrich

N-Iodosuccinimide

95%

Synonym(s):

1-iodo-pyrrolidine-2,5-dione, 1-iodoazolidine-2,5-dione, NIS, succiniodimide

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About This Item

Empirical Formula (Hill Notation):
C4H4INO2
CAS Number:
516-12-1
Molecular Weight:
224.98
Beilstein:
113917
EC Number:
208-221-6
MDL number:
MFCD00005512
UNSPSC Code:
12352101
PubChem Substance ID:
24853162
NACRES:
NA.22

Assay

95%

form

powder

mp

202-206 °C (lit.)

storage temp.

2-8°C

SMILES string

IN1C(=O)CCC1=O

InChI

1S/C4H4INO2/c5-6-3(7)1-2-4(6)8/h1-2H2

InChI key

LQZMLBORDGWNPD-UHFFFAOYSA-N

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Application

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.

Signal Word

Warning

Hazard Statements

H315,H317,H319,H341,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Muta. 2 - Skin Irrit. 2 - Skin Sens. 1B

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Earl S Ford
Chest, 147(4), 989-998 (2014-11-07)
Numbers and rates of hospitalizations and ED visits by patients with COPD are important metrics for surveillance purposes. The objective of this study was to examine trends in these rates from 2001 to 2012 among adults aged ≥ 18 years
Yoshihiko Yamamoto et al.
Journal of the American Chemical Society, 128(25), 8336-8340 (2006-06-22)
Highly substituted iodobenzenes were efficiently and regioselectively synthesized from readily available 1,6-diynes via two-step process consisting of silver-catalyzed Csp-H iodination and subsequent ruthenium-catalyzed [2 + 2 + 2] cycloaddition of resultant iododiynes. Some of the obtained iodobenzenes were subjected to
Taichi Kano et al.
Journal of the American Chemical Society, 130(12), 3728-3729 (2008-03-07)
A direct asymmetric iodination reaction of aldehydes with NIS was found to be catalyzed by the novel axially chiral bifunctional amino alcohol (S)-1d. This method represents the rare example of the catalytic and highly enantioselective synthesis of optically active alpha-iodoaldehydes.
Cong-Ying Zhou et al.
Organic letters, 12(9), 2104-2107 (2010-04-15)
Iodination of arene-containing natural products employing N-iodosuccinimide catalyzed by In(OTf)(3) at ambient temperature is reported as a versatile and mild method for natural product derivatization amenable to small scale. This process facilitates natural product derivatization of arene moieties for SAR
Canadian Journal of Chemistry, 84, 66-66 (2006)
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