366978

5-Fluoroisatin

98%

• Synonym(s): 5-Fluoro-2,3-indoledione, NSC 39161
• 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

Properties

• 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

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• 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