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366978

Sigma-Aldrich

5-Fluoroisatin

98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C8H4FNO2
CAS Number:
443-69-6
Molecular Weight:
165.12
MDL number:
MFCD00022795
UNSPSC Code:
12352100
PubChem Substance ID:
24862375
NACRES:
NA.22

Quality Level

100

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

Related Categories

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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