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366978 Sigma-Aldrich

5-Fluoroisatin

98%

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

  • CAS Number 443-69-6

  • Empirical Formula (Hill Notation) C8H4FNO2

  • Molecular Weight 165.12

  •  MDL number MFCD00022795

  •  PubChem Substance ID 24862375

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Properties

Related Categories Building Blocks, C7 to C9, Chemical Synthesis, Fluorinated Building Blocks, Heterocyclic Building Blocks,
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

Description

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

Packaging

5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles
Peer-Reviewed Papers
15

References

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