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MilliporeSigma

220051

N-Iodosuccinimide

95%

Synonym(s):

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

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5 G

$64.60

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$139.00

100 G

$513.00

$64.60


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About This Item

Empirical Formula (Hill Notation):
C4H4INO2
CAS Number:
Molecular Weight:
224.98
Beilstein/REAXYS Number:
113917
EC Number:
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

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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

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1 of 4

This Item
P7908226351369772
assay

95%

assay

-

assay

97%

assay

98%

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

-

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

−20°C

form

powder

form

powder

form

solid

form

solid

mp

202-206 °C (lit.)

mp

235-237 °C (lit.)

mp

130-133 °C (dec.) (lit.)

mp

120 °C (dec.) (lit.)

functional group

imide

functional group

-

functional group

imide, maleimide

functional group

-

Application

Highly substituted iodobenzenes prepared via an efficient 2-step process from 1,6-diynes.[1] Used with TFA to chemoselectively hydrolyze thioglycosides to 1-hydroxyglycosides.[2] Synthesis of vinyl sulfones from olefins and benzenesulfinic acid.[3]

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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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)
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
Christopher J T Hyland et al.
The Journal of organic chemistry, 71(22), 8658-8660 (2006-10-27)
Chiral gamma-substituted allenamides have been shown to undergo efficient gold-catalyzed and N-iodosuccinimide-mediated cyclization to highly functionalized dihydrofurans. These reactions proceed rapidly and without loss of stereochemistry.
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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    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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