4-Fluoroindole

CAS Number 387-43-9

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

A fluorinated indole

Used as a synthesis intermediate for dyes and APIs in application of drug discovery, OLEDs, DSSCs and bioimaging

Overview
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4-Fluoroindole (CAS number 387-43-9) is a mono-fluorinated indole, a benzene ring fused pyrrole heterocyclic compound. The derivatization of indole is versatile. Substitution of 1-position (on the nitrogen) is achieved with sodium hydride or potassium hydride making it a nucleophile. The 3-position can be activated with a Grignard reagent, namely methylmagnesium bromide or an organozinc compound. Position 2 of indole can be modified via directed ortho lithiation. After the expansion of chromophore, indole derivatives, triazatruxenes, are used as a donor unit in dye-sensitized solar cell with power conversion efficiency (PCE) of 13.6%.

Chemical structure of 4-fluoroindole with labelled positions

Indole is an intercellular signal molecule; hence it is a promising pharmaceutical molecular scaffold for active pharmaceutical ingredients (APIs). 4F-Indole improves the effectiveness of kanamycin (an aminoglycoside antibiotic) against Pseudomonas aeruginosa, a multi-drug resistant pathogen.

Combining the photophysio-properties and bioactivity, 4-fluoroindole is use in bioimaging, for instance monitoring cancer cells under anti-cancer treatments.

Multiple functional groups

For facile synthesis

Fluorinated indole building block

For drug discovery, OLEDs, and solar cells

Worldwide shipping

Quick and reliable shipping

High purity

>98% High purity

General Information

CAS Number	387-43-9
Chemical Formula	C₈H₆FN
Full Name	4-Fluoro-1H-indole
Molecular Weight	135.14 g/mol
Synonyms	N/A
Classification / Family	Fluorinated building blocks, Heterocyclic building block, APIs, OLEDs, DSSCs, Bioimaging

Chemical Structure

Product Details

Purity	98%
Melting Point	T_m = 30 °C – 32 °C
Appearance	White powder

MSDS Documentation

4-Fluoroindole MSDS Sheet

Literature and Reviews

4F-Indole enhances the susceptibility of pseudomonas aeruginosa to aminoglycoside antibiotics, Q. Dou et al., Microbiol. Spectr., 11(2), e04519–e04522(2023); DOI: 10.1128/spectrum.04519-22.
Fine tuning of blue photoluminescence from indoles for device fabrication, J. Hwu et al., J. Mater. Chem., 19, 3084–3090(2009); DOI: 10.1039/b821246e.
Indole fused heterocycles as sensitizers in dye-sensitized solar cells: an overview, P. Nitha et al., Mater. Adv., 2, 6136(2021); DOI: 10.1039/d1ma00499a.
Near-infrared-emitting meso-substituted heptamethine cyanine dyes: from the synthesis and photophysics to their use in bioimaging, L. Reimann et al., Chemosensors, 11, 47(2023); DOI: 10.3390/chemosensors11010047.
Recent advances in N-heterocyclic small molecules for synthesis and application in direct fluorescence cell imaging, Y. Li et al., Molecules, 28, 733(2023); DOI: 10.3390/molecules28020733.
Synthesis and biological evaluation of sclareolide-indole conjugates and their derivatives, Y. Cheng et al., Molecules, 28, 1737(2023), DOI: 10.3390/molecules28041737.

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