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114618

Sigma-Aldrich

Isatin

97%

Synonyme(s) :

2,3-Diketoindoline, 2,3-Dioxo-2,3-dihydroindole, 2,3-Dioxoindoline, o-Aminobenzoylformic anhydride, Isatic acid lactam, Isatinic acid anhydride, 2,3-Indolinedione, Isatine, NSC 9262

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About This Item

Formule empirique (notation de Hill) :
C8H5NO2
Numéro CAS:
91-56-5
Poids moléculaire :
147.13
Beilstein:
383659
Numéro CE :
202-077-8
Numéro MDL:
MFCD00005718
Code UNSPSC :
12352100
ID de substance PubChem :
24847187
Nomenclature NACRES :
NA.22

32.00 CHF

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Essai

97%

Forme

powder

Pf

193-195 °C (dec.) (lit.)

Solubilité

boiling water: soluble
diethyl ether: soluble
soluble

Groupe fonctionnel

ketone

Chaîne SMILES 

O=C1Nc2ccccc2C1=O

InChI

1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)

Clé InChI

JXDYKVIHCLTXOP-UHFFFAOYSA-N

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Catégories apparentées

Application

Isatin can be used as a reactant to prepare:
  • Phthalazinone derivatives.[1]
  • Spirooxindole derivatives.[2]
  • Agents against multidrug-resistant cells expressing P-glycoprotein.[3]
  • Thiazolidinones spiro-fused to indolin-2-ones as potent and selective inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B.[4]
  • Triazole-isatine compounds as potential antibacterial and antifungal agents.[5]
  • Biologically relevant scaffolds such as spiro[indole-thiazolidinones].[6]

It can be a reactant for:
  • Cascade reactions with heterocyclic ketene aminals.[7]
  • Knoevenagel condensation reactions.[8]

Isatin can also be used as a chromatographic spray reagent for amino acids, and also as a reference material in the preparation of indigo and Maya Blue. It is responsible for the yellow color exhibited by the "Maya Yellow" pigment.[9]
Isatin undergoes Pd(II)-catalyzed C-H addition by direct sp2/sp3 C-H bond activation to form 3-substituted-3-hydroxy-2-oxindoles[10]. Isatin derivatives (bis-Schiff base) are synthesized by the condensation of the natural or synthetic isatins with hydrazine[11].

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
0000432504
0000432504
0000358083
BCCL3419
0000336949

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Indirubin

Ozil, M.; et al.
J. Chem. Res. (M), 35, 268-268 (2011)
Gang-Wei Wang et al.
Organic letters, 15(20), 5270-5273 (2013-10-05)
The first Pd(II)-catalyzed C-H addition to isatins by direct sp(2)/sp(3) C-H bond activation for the construction of 3-substituted-3-hydroxy-2-oxindoles is reported. The bidentate nitrogen ligands were found to promote this reaction. Specifically, the preliminary bioassay indicated that 3-(5-chlorobenzoxazole)-3-hydroxy-N-benzyl-2-oxindole (2w) is a
Versatile three component procedure for combinatorial synthesis of biologically relevant scaffold spiro[indole-thiazolidinones] under aqueous conditions
Dandia, A.; et al.
Green Chemistry, 13, 1852-1852 (2011)
Demchuk, D. V.; et al.
Mendeleev Communications, 21, 224-224 (2011)
Chengyuan Liang et al.
European journal of medicinal chemistry, 74, 742-750 (2013-11-02)
Eighteen symmetrical bis-Schiff base derivatives of isatin were synthesized by condensation of the natural or synthetic isatins with hydrazine and were evaluated for their in vitro and in vivo antitumor activities. More than half of the obtained compounds showed potent
Afficher tous les articles scientifiques apparentés

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

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    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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  2. How can I determine the shelf life / expiration / retest date of this product?

    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/449/386/product-dating-information-mk.pdf

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