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366978

Sigma-Aldrich

5-Fluoroisatin

98%

Synonym(s):
NSC 39161, 5-Fluoro-2,3-indoledione
Empirical Formula (Hill Notation):
C8H4FNO2
CAS Number:
Molecular Weight:
165.12
MDL number:
PubChem Substance ID:

Quality Level

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

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

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
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

Packaging

5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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