2-Amino-4-fluorophenol

CAS Number 399-97-3

Chemistry Building Blocks, Fluorinated Building Blocks, Monomers

A fluorinated aminophenol building block

A precursor for synthesizing benzoxazole and benzoxazine derivatives in application of APIs and fluorescent dyes

Overview
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2-Amino-4-fluorophenol (CAS number 399-97-3), also referred to as 5-fluoro-2-hydroxyaniline, has a primary amine and a fluorine substituent at 2- and 4-positions. The amine and hydroxy groups in 2-amino-4-fluorophenol can coordinate to a metal centre to form 5-membered ring complexes. A heteroleptic tin(IV) complex with 2-amino-4-fluorophenol has shown in vitro cytotoxicity towards human cancer cells.

The ortho-position amine and hydroxyl groups make 2-amino-4-fluorophenol an ideal precursor for the syntheses of benzoxazoles and benzoxazines. A fluorescent benzoxazine derivative is synthesized from 2-amino-4-fluorophenol and 1,2-diketones. Functionalised benzoxazole can be obtained by reacting 2-amino-4-fluorophenol with 1,1'-dibromoethene derivatives.

Multiple functional groups

For facile synthesis

Fluorinated aniline/phenol building block

For drug discovery, fluorescent dyes, and organic synthesis

Worldwide shipping

Quick and reliable shipping

High purity

>97% High purity

General Information

CAS Number	399-97-3
Chemical Formula	C₆H₆FNO
Full Name	2-Amino-4-fluorophenol
Molecular Weight	127.12 g/mol
Synonyms	5-Fluoro-2-hydroxyaniline
Classification / Family	Fluorinated building block, APIs and fluorescent dyes

Chemical Structure

Product Details

Purity	97%
Melting Point	T_m = 130 – 135 °C
Appearance	Brown powder

MSDS Documentation

2-Amino-4-fluorophenol MSDS Sheet

Literature and Reviews

4-Benzoyl-2-(4-bromophenyl)-1-(4-methoxyphenyl)-1,2-dihydropyrimidino[4,3-c][1,4]benzoxazine-3,5-dione, E. Khramtsova et al., Molbank, 2023, M1583(2023); DOI:10.3390/M1583.
Direct access to highly functionalised benzimidazoles and benzoxazoles from a common precursor, A. Garrido et al., Synthesis, 51, 4006–4013(2019); DOI: 10.1055/s-0039-1690153.
Structure-based optimization of small molecule human galactokinase inhibitors, L. Liu et al., J. Med. Chem., 64(18), 13551–13571(2021); DOI: 10.1021/acs.jmedchem.1c00945.
Synthesis and biological evaluation of potential acetylcholinesterase inhibitors based on a benzoxazine core, C. Méndez-Rojas et al., Arch Pharm. Chem. Life Sci., 315(5), 1800024(2018); DOI: 10.1002/ardp.201800024.
Synthesis of some fluorescent dyes based on stilbene derivatives with various substituents and their effects on the absorption maxima, Y.-G. Lee et al., Appl. Sci., 13, 5543(2023); DOI: 10.3390/app13095543.
Schiff base Sn(IV) complexes as cytotoxic agents: Synthesis, structure, isosteric and bioisosteric replacement, J. Galván-Hidalgo et al., J. Organomet. Chem., 848(15), 332-343(2017); DOI: 10.1016/j.jorganchem.2017.08.017.

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