6-Fluoroindole

CAS Number 399-51-9

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

A fluorinated indole

Used as a synthesis intermediate for bioactive compounds and polyindoles in application of APIs, fluorine-labelling compounds, OLEDs, semiconductors and DSSCs

Overview
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6-Fluoroindole (CAS number 399-51-9) is a fluorinated (6-position) indole, a benzene ring fused pyrrole heterocycle. 6-Fluoroindole is an antimicrobial which works by interfering with the quorum sensing system of the pathogens. 6-Fluoroindole inhibits the biofilm formation that causes infections.

6-Fluoroindole can be easily functionalized with Bpin groups (pinacol boronate) at 2-, 3-, 4-, 5- and 7-positions selectively with iridium-catalysed borylation and bismuth-catalysed protodeboronation. The modification to 6-fluoroindole allows late-stage functionalization on different positions of the molecule, expanding the molecular library for drug discovery.

6-Fluoroindole is also used to label bacteria cells (Escherichia coli) in order to study the protein-protein interaction in vitro with ¹⁹F NMR and ¹⁵N-¹H HSQC (heteronuclear single quantum coherence) NMR.

Multiple functional groups

For facile synthesis

Fluorinated indole building block

For drug discovery, OLEDs, and semiconductors

Worldwide shipping

Quick and reliable shipping

High purity

>98% High purity

General Information

CAS Number	399-51-9
Chemical Formula	C₈H₆FN
Full Name	6-Fluoro-1H-indole
Molecular Weight	135.14 g/mol
Synonyms	N/A
Classification / Family	Fluorinated building block, Heterocyclic building block, APIs, OLEDs, Semiconductors, DSSCs

Chemical Structure

Product Details

Purity	98%
Melting Point	T_m = 72 °C – 76 °C
Appearance	Off-white powder

MSDS Documentation

6-Fluoroindole MSDS Sheet

Literature and Reviews

Antibiofilm and antivirulence properties of indoles against Serratia marcescens, S. Sethupathy et al., Front. Microbiol., 11, 584812(2020); DOI: 10.3389/fmicb.2020.584812.
Bismuth acetate as a catalyst of the sequential protodeboronation of di- and triborylated indoles, F. Shen et al., Org Lett., 18(7), 1554–1557(2016); DOI: 10.1021/acs.orglett.6b00356.
Hexafluoroisopropyl carbamates as selective MAGL and dual MAGL/FAAH inhibitors: biochemical and physiochemical properties, M. Barth et al., ChemMedChem, 17, e202100757(2022); DOI: 10.1002/cmdc.202100757.
Fluoro-recognition: new in vivo fluorescent assay for toluene dioxygenase probing induction by and metabolism of polyfluorinated compounds, K. Aukema et al., Environ Microbiol., 24, 5202–5216(2022); DOI: 10.1111/1462-2920.16187.
The intracellular environment affects protein-protein interactions, S, Speer et al., PNAS, 18(11), e2019918118(2021); DOI: 10.1073/pnas.2019918118.

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