366978
5-Fluoroisatin
97%
Synonym(s):
5-Fluoro-2,3-indoledione, NSC 39161
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About This Item
Empirical Formula (Hill Notation):
C8H4FNO2
CAS Number:
Molecular Weight:
165.12
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Product Name
5-Fluoroisatin, 97%
InChI
1S/C8H4FNO2/c9-4-1-2-6-5(3-4)7(11)8(12)10-6/h1-3H,(H,10,11,12)
SMILES string
Fc1ccc2NC(=O)C(=O)c2c1
InChI key
GKODDAXOSGGARJ-UHFFFAOYSA-N
mp
224-227 °C (lit.)
functional group
fluoro
ketone
Quality Level
assay
97%
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
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).
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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
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)
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
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