5-Fluorooxindole

CAS Number 56341-41-4

Chemistry Building Blocks, Fluorinated Building Blocks, Heterocyclic Building Blocks, Monomers

A fluorinated heterocyclic building

Used as a synthesis intermediate for macromolecules and fluorescent dyes in application of APIs, bioimaging, solar cells and OLEDs

Overview
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5-Fluorooxindole (CAS number 56341-41-4), a fluorinated oxindole, is a benzene ring fused pyrrolidone (γ-lactam) with a fluorine substituent at 5-position. 5-Fluorooxindole has proven effectiveness on alleviating inflammatory pain and improving the analgesic effects of morphine. 5-Fluorooxindole inhibits the plasticity changes, oxidative stress, and inflammatory responses cause by peripheral inflammation. The derivatives of 5-fluorooxindole are used as α-glucosidase inhibitors for prevention and treatment of type 2 diabetes.

The 3-position of 5-fluorooxindole can be functionalised through an aldol condensation reaction in a basic solution. With the expanded chromophore, 5-fluorooxindole is used as an acceptor in dye-sensitized solar cells (DSSCs) with power conversion efficiency of 6.35%. Oxindole modified polymers are exploited as donors in non-fullerene polymer solar cells with Y6 (BTP-4F) as acceptor with power conversion efficiency up to 8.27%.

Multiple functional groups

For facile synthesis

Fluorinated oxindole building block

For drug discovery, solar cells, and OLEDs

Worldwide shipping

Quick and reliable shipping

High purity

>98% High purity

General Information

CAS Number	56341-41-4
Chemical Formula	C₈H₆FNO
Full Name	5-Fluoro-2-oxindole
Molecular Weight	151.14 g/mol
Synonyms	5-Fluoro-1,3-dihydroindol-2-one, 5-Fluoro-2,3-dihydro-2-oxoindole
Classification / Family	Fluorinated building block, Heterocyclic building block, OLEDs, Solar cells

Chemical Structure

Product Details

Purity	98%
Melting Point	T_m = 143 °C – 147 °C
Appearance	Off-white to pale pink/beige powder

MSDS Documentation

5-Fluorooxindole MSDS Sheet

Literature and Reviews

Bis-arylidene oxindole-betulinic acid conjugate: a fluorescent cancer cell detector with potent anticancer activity, A. Pal et al, ACS Med. Chem. Lett., 6, 612−616(2015); DOI: 10.1021/acsmedchemlett.5b00095.
New oxindole-bridged acceptors for organic sensitizers: substitution and performance studies in dye-sensitized solar cells, Y. Tingare et al., Molecules, 25, 2159(2020); DOI: 10.3390/molecules25092159.
Synthesis and biological evaluation of 5-fluoro-2-oxindole derivatives as potential α-glucosidase inhibitors, J. Lin et al., Front. Chem., 10, 928295(2022); DOI: 10.3389/fchem.2022.928295.
The antinociceptive, antioxidant and anti-inflammatory effects of 5-fluoro-2-oxindole during inflammatory pain, Antioxidants, 9, 1249(2020); DOI: 10.3390/antiox9121249.
The development of photoactivated fluorescent N-hydroxyoxindoles and its application for cell-selective imaging, J. Lai et al., Chem. Eur. J., 22, 6361(2022); DOI: 10.1002/chem.201600547.
Simple (thienylmethylene)oxindole-based polymer materials as donors for efficient non-fullerene polymer solar cells, H. Li et al., Nano Select 2, 417–424(2021); DOI. 10.1002/nano.202000198.

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