Skip to Content
Merck
All Photos(3)

Key Documents

114618

Sigma-Aldrich

Isatin

97%

Synonym(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

Sign Into View Organizational & Contract Pricing

Select a Size

5 G
$51.60
100 G
$55.10
500 G
$174.00

$51.60


Please contact Customer Service for Availability

Request a Bulk Order

Select a Size

Change View
5 G
$51.60
100 G
$55.10
500 G
$174.00

About This Item

Empirical Formula (Hill Notation):
C8H5NO2
CAS Number:
Molecular Weight:
147.13
Beilstein:
383659
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

$51.60


Please contact Customer Service for Availability

Request a Bulk Order

Quality Level

Assay

97%

form

powder

mp

193-195 °C (dec.) (lit.)

solubility

boiling water: soluble
diethyl ether: soluble
soluble

functional group

ketone

SMILES string

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)

InChI key

JXDYKVIHCLTXOP-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

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].

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Novel Synthesis of Some Phthalazinone Derivatives
Mahmoud, M. R.; et al.
Chin. J. Chem., 29, 1446-1450 (2011)
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)
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)
Ozil, M.; et al.
J. Chem. Res. (M), 35, 268-268 (2011)

Questions

1–2 of 2 Questions  
  1. 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

      Helpful?

  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

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service