6-Fluoroindole-2-carboxylic acid

CAS Number 3093-97-8

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

6-Fluoroindole-2-carboxylic acid CAS 3093-97-8

A fluorinated indole with a carboxylic acid anchoring group

Used as a synthesis intermediate for metal complexes, macromolecules, and bioactive compounds in application of APIs, solar cells and OFETs

Overview
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6-Fluoroindole-2-carboxylic acid (CAS number 3093-97-8) is a fluorinated indole derivative, having a fluorine at 6-position and a carboxylic acid at 2-position. The secondary amine and carboxylic acid in 6-Fluoroindole-2-carboxylic acid form an α-amino acid moiety. This allows 6-fluoroindole-2-carboxylic acid to have a zwitterionic form where the proton of the carboxylic acid is transferred to the amine. In fluorescence spectra, the neutral form and zwitterionic form of 6-fluoroindole-2-carboxylic acid have different emission band at 332 and 370 nm respectively, forming a broad fluorescence emission peak.

The zwitterionic form of 6-fluoroindole-2-carboxylic acid

The carboxylic acid group in 6-fluoroindole-2-carboxylic acid can bind to copper(II), yielding a binuclear complex. The complex shows anti-cancer activity towards breast cancer cell lines (MDA-MB-231 and MCF-7) with percentage of inhibition of 90% at 20 µM concentration.

6-Fluoroindole-2-carboxylic acid can be used to synthesise triindoles, via a palladium catalysed decarboxylative reaction. Triindoles are used as semiconductors in OFETs with field effect mobility of 0.03 cm²V^-1S^-1, as well as hole transport layers in solar cells.

Multiple functional groups

For facile synthesis

Fluorinated indole building block

For drug discovery, solar cells, and OLEDs

Worldwide shipping

Quick and reliable shipping

High purity

>98% High purity

General Information

CAS Number	3093-97-8
Chemical Formula	C₉H₆FNO2
Full Name	6-Fluoro-1H-indole-2-carboxylic acid
Molecular Weight	179.15 g/mol
Synonyms	N/A
Classification / Family	Fluorinated building block, Heterocyclic building block, APIs, OFETs, Solar cells, Semiconductors

Chemical Structure

Product Details

Purity	97%
Melting Point	T_m = 244 °C – 250 °C
Appearance	White to off-white powder

MSDS Documentation

6-Fluoroindole-2-carboxylic acid MSDS Sheet

Literature and Reviews

Excited state proton transfer in indole-2-carboxylic acid and indole-5-carboxylic acid, P. Bangal et al., J. Phys. Chem. A, 103, 8585-8594(1999); DOI: 10.1021/jp991884f.
Halogenated indoles decease the virulence of Vibrio campbellii in a gnotobiotic brine shrimp model, S. Zhang et al., Microbiol. Spectr., 10(5), e02689-22(2022); DOI: 10.1128/spectrum.02689-22.
In vitro DNA-binding, antioxidant and anticancer anctivity of indole-2-carboxylic acid dinuclear copper(II) complex, X. Wang et al., Molecules, 22, 171(2017); DOI: 10.3390/molecules22010171.
Novel indole‐2‐carboxylic acid analogues: Synthesis and a new light in to their antioxidant potentials, N. Naik et al., Eur. J. Chem., 3(2), 214‐219(2012); DOI: 10.5155/eurjchem.3.2.214‐219.588.
Palladium-catalysed decarboxylative nitrile insertion via C-H activation or self-coupling of indole-2-carboxylic acids: A new route to indolocarbolines and triindoles, N. Tulichala et al., Chem. Commun., 51, 12008-12011(2015); DOI: 10.1039/C5CC03160E.
Self-assembly of indole-2-carboxylic acid at graphite and gold surfaces, F. De Marchi et al., J. Chem. Phys., 142, 101923(2015); DOI: 10.1063/1.4908143.

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