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114618

Sigma-Aldrich

Isatin

97%

Sinónimos:

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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5 G
MXP 869.00
100 G
MXP 1,120.00
500 G
MXP 3,662.00

MXP 869.00

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5 G
MXP 869.00
100 G
MXP 1,120.00
500 G
MXP 3,662.00

About This Item

Fórmula empírica (notación de Hill):
C8H5NO2
Número de CAS:
91-56-5
Peso molecular:
147.13
Beilstein:
383659
Número CE:
202-077-8
Número MDL:
MFCD00005718
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
24847187
NACRES:
NA.22

MXP 869.00

Disponible para envío el21 de abril de 2025Detalles

Solicitar un pedido a granel

Nivel de calidad

100

Ensayo

97%

Formulario

powder

mp

193-195 °C (dec.) (lit.)

solubilidad

boiling water: soluble
diethyl ether: soluble
soluble

grupo funcional

ketone

cadena 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)

Clave InChI

JXDYKVIHCLTXOP-UHFFFAOYSA-N

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Aplicación

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].

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 1

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
0000432504
0000432504
0000358083
BCCL3419
0000336949

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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
Fuchao Yu et al.
Organic letters, 13(18), 4782-4785 (2011-08-19)
A concise and efficient route for the synthesis of highly substituted imidazopyrroloquinoline derivatives by simply refluxing a reaction mixture of different types of isatins and heterocyclic ketene aminals (HKAs) by acetic acid was developed. This method is suitable for combinatorial
From Maya Blue to "Maya Yellow": a connection between ancient nanostructured materials from the voltammetry of microparticles.
Antonio Doménech et al.
Angewandte Chemie (International ed. in English), 50(25), 5741-5744 (2011-05-11)
Step-economic, efficient, ZnS nanoparticle-catalyzed synthesis of spirooxindole derivatives in aqueous medium viaKnoevenagel condensation followed by Michael addition
Dandia, A.; et al.
Green Chemistry, 13, 2135-2145 (2011)
Hui Lv et al.
Organic letters, 14(21), 5412-5415 (2012-10-16)
An N-heterocyclic carbene (NHC)-catalyzed annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-γ-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities (up to >20:1 dr and 99% ee).
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  1. How can I determine the shelf life / expiration / retest date of this product?

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    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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  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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