5-(Trifluoromethoxy)isatin

CAS Number 169037-23-4

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

5-(Trifluoromethoxy)isatin CAS 169037-23-4

A fluorinated heterocyclic building block

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

Overview
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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

For facile synthesis

Fluorinated isatin building block

For drug discovery, solar cells, and OLEDs

Worldwide shipping

Quick and reliable shipping

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

Product Details

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

MSDS Documentation

5-(Trifluoromethoxy)isatin MSDS Sheet

Literature and Reviews

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.
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.
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.
Synthesis of novel methanofullerenes spiro-coupled with the indolinone fragment and prospects of their use in light-absorbing layers of plastic solar cells, I. Romanova et al., Russ. Chem. Bull., 60(5), 867-872(2011); DOI: 10.1007/s11172-011-0136-5.
The aggregation-induced emission enhancement properties of BF₂ complex isatin-phenylhydrazone: Synthesis and fluorescence characteristics, J. Zheng et al., Dyes Pigm., 113, 502-509(2015); DOI: 10.1016/j.dyepig.2014.09.025.

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