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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:
Molecular Weight:
224.98
Beilstein:
113917
EC Number:
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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
Canadian Journal of Chemistry, 84, 66-66 (2006)
Mark C Dobish et al.
Journal of the American Chemical Society, 134(14), 6068-6071 (2012-04-03)
Highly enantioselective halolactonizations have been developed that employ a chiral proton catalyst-N-iodosuccinimide (NIS) reagent system in which the Brønsted acid is used at catalyst loadings as low as 1 mol %. An approach that modulates the achiral counterion (equimolar to
Stephen W Waldo et al.
Journal of the American College of Cardiology, 65(11), 1119-1126 (2015-03-21)
Public reporting of procedural outcomes may create disincentives to provide percutaneous coronary intervention (PCI) for critically ill patients. This study evaluated the association between public reporting with procedural management and outcomes among patients with acute myocardial infarction (AMI). Using the
Jasper Dinkelaar et al.
Carbohydrate research, 341(10), 1723-1729 (2006-04-06)
A variety of thioglycosides are chemoselectively hydrolyzed to the corresponding 1-hydroxy glycosides using equimolar amounts of NIS/TFA as promoter systems.

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