MilliporeSigma
All Photos(1)

Documents

366978

Sigma-Aldrich

5-Fluoroisatin

98%

Sign Into View Organizational & Contract Pricing

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

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

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
679119746029526274
5-Fluoroisatin 98%

Sigma-Aldrich

366978

5-Fluoroisatin

7-Fluoroisatin 96%

Sigma-Aldrich

679119

7-Fluoroisatin

5-Fluoroindoline 97%

Sigma-Aldrich

746029

5-Fluoroindoline

mp

224-227 °C (lit.)

mp

192-196 °C

mp

-

mp

82-85 °C (lit.)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

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

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

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’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Slide 1 of 1

1 of 1

7-Bromoisatin 96%

Sigma-Aldrich

679127

7-Bromoisatin

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service