2,3,5,6-Tetrafluoro-4-hydroxybenzoic acid

CAS Number 652-34-6

Chemistry Building Blocks, Fluorinated Building Blocks, Monomers

2,3,5,6-Tetrafluoro-4-hydroxybenzoic acid MSDS

2,3,5,6-Tetrafluoro-4-hydroxybenzoic acid CAS 652-34-6

A perfluorinated hydroxybenzoic acid building block

Used as a synthesis intermediate for APIs and quenched activity-based probe for bioimaging applications.

Overview
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2,3,5,6-Tetrafluoro-4-hydroxybenzoic acid (CAS number 652-34-6) is a perfluorinated para-hydroxybenzoic acid building block. Due to its perfluorination, 2,3,5,6-tetrafluoro-4-hydroxybenzoic acid is relatively acidic with an observed pK_a of 5.3, compared to non-fluorinated 4-hydroxybenzoic acid (pK_a of 9.3). 2,3,5,6-Tetrafluoro-4-hydroxybenzoic acid is a precursor used to synthesise BMV109 which serves as a fluorescent activity-based probe for bioimaging. This probe is intrinsically non-fluorescent but only becomes fluorescent after reacting with a target protease.

2,3,5,6-Tetrafluoro-4-hydroxybenzoic acid is also employed in the preparation of novel inhibitors for protein farnesyltransferase (FTase) and geranylgeranyltransferase (GGTase), through Mitsunobu reaction. Enzyme inhibition studies demonstrate a potency of 2.9 µM against FTase and 7.5 µM against GGTase.

Multiple functional groups

For facile synthesis

Fluorinated hydroxybenzoic acid building block

For drug discovery, medicinal chemistry and biochemistry research

Worldwide shipping

Quick and reliable shipping

High purity

>98% High purity

General Information

CAS Number	652-34-6
Chemical Formula	C₇H₂F₄O₃
Full Name	2,3,5,6-Tetrafluoro-4-hydroxybenzoic acid
Molecular Weight	210.08 g/mol
Synonyms	4-Carboxy-2,3,5,6-tetrafluorophenol, 4-Hydroxy-2,3,5,6-tetrafluorobenzoic acid
Classification / Family	Fluorinated building blocks, Benzoic acid building blocks, APIs, Bioimaging

Chemical Structure

Product Details

Purity	98%
Melting Point	T_m = 151 °C – 153 °C
Appearance	White powder

MSDS Documentation

2,3,5,6-Tetrafluoro-4-hydroxybenzoic acid MSDS Sheet

Literature and Reviews

Live cell imaging and profiling of cysteine cathepsin activity using a quenched activity-based probe, L. Edgington-Mitchell et al., Methods Mol. Biol., 1491, 145-159(2017); DOI: 10.1007/978-1-4939-6439-0_11.
An improved quenched fluorescent probe for imaging of cysteine cathepsin activity, M. Verdoes et al., J. Am. Chem. Soc., 135(39), 14726–14730(2013); DOI: 10.1021/ja4056068.
Synthesis of the farnesyl ether 2,3,5-trifluoro-6-hydroxy-4-[(E,E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yloxy]nitrobenzene, and related compounds containing a substituted hydroxytrifluorophenyl residue: novel inhibitors of protein farnesyltransferase, geranylgeranyltransferase I and squalene synthase, J. Marriott et al., J. Chem. Soc., Perkin Trans., 1, 4265–4278(2000); DOI: 10.1039/b007101n.
TEAC antioxidant activity of 4-hydroxybenzoates, B. Tyrakowska et al., Free Radic. Biol. Med., 27, 1427–1436(1999); DOI: 10.1016/S0891-5849(99)00192-6.

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