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220051

Sigma-Aldrich

N-Iodosuccinimide

95%

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Synonym(s):
1-iodo-pyrrolidine-2,5-dione, 1-iodoazolidine-2,5-dione, NIS, succiniodimide
Empirical Formula (Hill Notation):
C4H4INO2
CAS Number:
516-12-1
Molecular Weight:
224.98
Beilstein:
113917
EC Number:
208-221-6
MDL number:
MFCD00005512
PubChem Substance ID:
24853162
NACRES:
NA.22

Quality Level

200

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 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

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Canadian Journal of Chemistry, 84, 66-66 (2006)
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
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
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
Yuanxun Zhu et al.
Organic letters, 13(5), 1024-1027 (2011-01-28)
An efficient and straightforward strategy for the synthesis of N-(2-haloinden-1-yl)arenesulfonamides from propargylic alcohols and sulfonamides is described. Allenesulfonamide is postulated to be the key intermediate for this tandem transformation.
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