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366978

Sigma-Aldrich

5-Fluoroisatin

98%

Sinónimos:

5-Fluoro-2,3-indoledione, NSC 39161

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About This Item

Fórmula empírica (notación de Hill):
C8H4FNO2
Número de CAS:
443-69-6
Peso molecular:
165.12
MDL number:
MFCD00022795
UNSPSC Code:
12352100
PubChem Substance ID:
24862375
NACRES:
NA.22

assay

98%

mp

224-227 °C (lit.)

SMILES string

Fc1ccc2NC(=O)C(=O)c2c1

InChI

1S/C8H4FNO2/c9-4-1-2-6-5(3-4)7(11)8(12)10-6/h1-3H,(H,10,11,12)

InChI key

GKODDAXOSGGARJ-UHFFFAOYSA-N

Categorías relacionadas

General description

5-Fluoroisatin has been reported as the precursor of the Sunitinib (Sutent) drug. 5-Fluoroisatin has been approved by the Food and Drugs Administration (FDA) in 2006 for the treatment of renal cell carcinoma (RCC) and gastrointestinal stromal tumor (GIST).

Application

5-Fluoroisatin may be used:
  • as reaction-based probe for live-cell detection of peroxynitrite by 19F magnetic resonance spectroscopy
  • in non-invasive detection of peroxynitrite (ONOO(-)) formation in living lung epithelial cells stimulated with interferon-γ (IFN-γ)
  • in the synthesis of bis-Schiff bases, via condensation with aromatic primary bis-amines in water suspension medium without using any organic solvent or acid catalyst
  • in the synthesis of 3-acetonyl-5-fluoro-3-hydroxyoxindole
Reactant for preparation of:
  • Spiro[indole-thiazolidinones] as biologically relevan synthesis scaffolds
  • Potential antimycobacterial agents
  • Inhibitors of c-Met kinase
  • Inhibitors of TAK1 kinase
  • Herpes simplex virus inhibitors
  • IKKβ inhibitors
  • Inhibitors of vitiligo disease
  • Potential drug candidates with anti-HIV activity and anti-tubercular activity

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sigma-Aldrich

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A Novel Preparation of a-Substituted Tryptamines from Isatins.
Franklin CS and White AC.
Journal of the Chemical Society, 2, 1335-1337 (1963)
A A Jarrahpour et al.
Molecules (Basel, Switzerland), 11(1), 59-63 (2007-10-27)
Condensation of aromatic primary bis-amines with isatin (1H-indole-2,3-dione) and 5-flouroisatin occurred cleanly and efficiently in a water suspension medium without using any organic solvent or acid catalyst. The corresponding bis-Schiff bases were obtained in good yields and were easily isolated
Counter-Current chromatography separation of isatin derivatives using the sandmeyer methodology.
Almeida MR, et al.
Journal of the Brazilian Chemical Society, 21(4), 764-769 (2010)
Kevin J Bruemmer et al.
Chemical communications (Cambridge, England), 50(82), 12311-12314 (2014-09-03)
We report a newly discovered oxidative decarbonylation reaction of isatins that is selectively mediated by peroxynitrite (ONOO(-)) to provide anthranilic acid derivatives. We have harnessed this rapid and selective transformation to develop two reaction-based probes, 5-fluoroisatin and 6-fluoroisatin, for the

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