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Product Code B1741-5g
Price $144 ex. VAT

A fluorinated heterocyclic building block

Used as a synthesis intermediate for organic and metal complexes in application of fluorescence dyes, OLEDs, and solar cells

Specifications | MSDS | Literature and Reviews

5-(Trifluoromethoxy)isatin (CAS number 169037-23-4), a derivative of indole, has two carbonyls at 2,3-position and a trifluoromethoxy at 5-position. In 5-(trifluoromethoxy)isatin, the carbonyl at 3-position is more reactive than the amide carbonyl at 2-position, thus it is readily functionalized under nucleophilic substitution. The nucleophilic substitution can also be enantioselective with the addition of chiral catalysts, with up to 92% ee (enantiomeric excess).

5-(Trifluoromethoxy)isatin is used to synthesize luminescent gold(I) complexes, displaying an emission at 400 nm. The isatin-gold complexes show cytotoxicity to cancer cells with half-maximal inhibitory concentration (IC50) as low as 0.28 μM. 5-(Trifluoromethoxy)isatin is also used to modify rhodamine in application of selectively detection of Cr3+. An isatin decorated fullerene (C60) has improved miscibility to P3HT in heterojunction organic solar cells.

Multiple functional groups

Multiple functional groups

For facile synthesis

Fluorinated building block

Fluorinated isatin building block

For drug discovery, solar cells, and OLEDs

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High purity 169037-23-4

High purity

>98% High purity

General Information

CAS Number 169037-23-4
Chemical Formula C9H4F3NO3
Full Name 5-(Trifluoromethoxy)-1H-indole-2,3-dione
Molecular Weight 231.13 g/mol
Synonyms 5-(Trifluoromethoxy)-2,3-indolinedione
Classification / Family Fluorinated building blocks, Heterocyclic building blocks, Solar cells, OLEDs

Chemical Structure

5-(Trifluoromethoxy)isatin chemical structure, CAS 169037-23-4
5-(Trifluoromethoxy)isatin chemical structure, CAS 169037-23-4

Product Details

Purity 98%
Melting Point Tm = 170 °C – 172 °C
Appearance Orange to brown powder

MSDS Documentation

5-(Trifluoromethoxy)isatin5-(Trifluoromethoxy)isatin MSDS Sheet

Literature and Reviews

  1. A novel Cr3+ fluorescence turn-on probe based on rhodamine and isatin framework, A. Dhara et al., J. Fluoresc., 25, 1921–1929 (2015); DOI: 10.1007/s10895-015-1684-0.
  2. Highly enantioselective construction of 3-hydroxy oxindole through a decarboxylative aldol addition of trifluoromethyl α-fluorinated gem-diol to N-benzyl isatins, I. Saidalimu et al., Angew. Chem. Int. Ed., 52, 5566–5570(2013); DOI: 10.1002/anie.201301443.
  3. Bioactive and luminescent indole and isatin based gold(I) derivatives, V. Fernández-Moreira et al., Dalton Trans., 48, 3098–3108(2019); DOI: 10.1039/C8DT00298C.
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