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

CAS Number 652-34-6

Chemistry Building Blocks, Fluorinated Building Blocks, Materials, Monomers

Product Code B2871-1g
Price £80 ex. VAT

A perfluorinated hydroxybenzoic acid building block

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

Specifications | MSDS | Literature and Reviews

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 pKa of 5.3, compared to non-fluorinated 4-hydroxybenzoic acid (pKa 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

Multiple functional groups

For facile synthesis

Fluorinated building block

Fluorinated hydroxybenzoic acid building block

For drug discovery, medicinal chemistry and biochemistry research

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High purity 652-34-6

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

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

Product Details

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

MSDS Documentation

2,3,5,6-Tetrafluoro-4-hydroxybenzoic acid2,3,5,6-Tetrafluoro-4-hydroxybenzoic acid MSDS Sheet

Literature and Reviews

  1. 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.
  2. 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.
  3. 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.

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