5-Fluoroindole

CAS Number 399-52-0

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

A fluorinated indole

Used as a synthesis intermediate for APIs and polyindoles in application of biosynthesis, OLEDs, DSSCs and semiconductors

Overview
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5-Fluoroindole (CAS number 399-52-0), derived from indole, a bicyclic heterocycle, has a fluorine substituent at 5-position. 5-Fluoroindole is applied as a fluorine labelled indole in tryptophan biosynthesis which can be monitored by ¹⁹F NMR. The conversion of 5-fluoroindole to 5-fluorotryphtophan is catalyzed by an enzyme synthase with L-serine in proliferating Escherichia coli cells.

5-Fluoroindole is also used to synthesize polyindoles. The oxidative potential of 5-fluoroindole is 1.05 V vs SCE (saturated calomel electrode), which allows it to be easily polymerized electrochemically. The fluorinated polyindoles show conductivity of 7.1 × 10^-2 S/cm as well as redox properties. Polymers of 5-fluoroindole also exhibit blue light emission in fluorescent spectroscopy, suggesting their potential applications in OLEDs.

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	399-52-0
Chemical Formula	C₈H₆FN
Full Name	5-Fluoro-1H-indole
Molecular Weight	135.14 g/mol
Synonyms	N/A
Classification / Family	Fluorinated building block, Heterocyclic building block, APIs, OLEDs, DSSCs, Semiconductors

Chemical Structure

Product Details

Purity	98%
Melting Point	T_m = 45 °C – 48 °C
Appearance	Off-white to pale beige powder

MSDS Documentation

5-Fluoroindole MSDS Sheet

Literature and Reviews

Low-potential electrochemical polymerization of 5-fluoroindole and characterization of its polymers, G. Nie et al., J. Electroanal. Chem., 604(2), 125−132(2007); DOI: 10.1016/j.jelechem.2007.03.010.
Assessing the applicability of ¹⁹F labeled tryptophan residues to quantify protein dynamics, C. Krempl et al., J. Biomol. NMR, 77, 55−67(2023); DOI: 10.1007/s10858-022-00411-2.
Modulation of the L_a/L_b mixing in an indole derivative: a position-dependent study using 4-, 5-, and 6-fluoroindole, J. Wilke et al., J. Phys. Chem. A, 121, 1597−1606(2017); DOI: 10.1021/acs.jpca.6b12605.
Multiomics analysis provides insight into the laboratory evolution of Escherichia coli toward the metabolic usage of fluorinated indoles, F. Agostini et al., ACS Cent. Sci., 7, 81−92(2021); DOI: 10.1021/acscentsci.0c00679.
Polymer-induced biofilms for enhanced biocatalysis, P. Adoni et al., Mater. Horiz., 9, 2592(2022); DOI: 10.1039/d2mh00607c.

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