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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:
Molecular Weight:
224.98
Beilstein/REAXYS Number:
113917
EC Number:
MDL number:
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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1 of 4

This Item
P7908226351369772
N-Iodosuccinimide 95%

220051

N-Iodosuccinimide

N-(1-Pyrenyl)maleimide

P7908

N-(1-Pyrenyl)maleimide

N-Hydroxymaleimide 97%

226351

N-Hydroxymaleimide

2,5-Oxazolidinedione 98%

369772

2,5-Oxazolidinedione

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

−20°C

mp

202-206 °C (lit.)

mp

235-237 °C (lit.)

mp

130-133 °C (dec.) (lit.)

mp

120 °C (dec.) (lit.)

form

powder

form

powder

form

solid

form

solid

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

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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
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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

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