220051
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
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
EC Number:
208-221-6
Beilstein/REAXYS Number:
113917
MDL number:
Assay:
95%
Form:
powder
Quality Level
assay
95%
form
powder
mp
202-206 °C (lit.)
functional group
imide
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
Related Categories
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.
signalword
Warning
Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
hcodes
Hazard Classifications
Aquatic Acute 1 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1B
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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
Abby J Isaacs et al.
The Journal of thoracic and cardiovascular surgery, 149(5), 1262-1269 (2015-03-21)
Substantial controversy surrounds the choice between a mechanical versus bioprosthetic prosthesis for aortic valve replacement (AVR), based on age. This study aims to investigate national trends and in-hospital outcomes of the 2 prosthesis choices. All patients aged >18 years in
Canadian Journal of Chemistry, 84, 66-66 (2006)
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.
Manjunath Lamani et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(46), 14638-14642 (2012-10-09)
Single-step amination: the N-iodosuccinimide (NIS)-catalyzed amidation of acetophenone derivatives by using tert-butylhydroperoxide (TBHP) as an oxidant is presented. A variety of acetyl derivatives of heterocyclic compounds were easily converted to their corresponding ketoamides under these conditions. A new, NIS-catalyzed amination
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