214554-18-4

Usage

Uses

Used in Pharmaceutical Industry:
2-Fluoro-4-(hydroxymethyl)benzoic acid is used as a fluorinated linker for the preparation of pilicide libraries. Its fluorinated nature and hydroxymethyl group provide a versatile platform for the development of new pilicides, which are compounds that inhibit bacterial protein synthesis by targeting the ribosome.
As a reagent in the synthesis of pilicides, 2-fluoro-4-(hydroxymethyl)benzoic acid plays a crucial role in the development of new antibiotics to combat antibiotic-resistant bacteria. The fluorinated linker enhances the binding affinity and specificity of the resulting pilicides, potentially leading to more effective treatments for bacterial infections.

InChI:InChI=1/C8H7FO3/c9-7-3-5(4-10)1-2-6(7)8(11)12/h1-3,10H,4H2,(H,11,12)

Upstream product

• 124-38-9 carbon dioxide 
• 456-47-3 3-fluoro-benzenemethanol 
• 481075-27-8 1-fluoro-3-[(methoxymethoxy)methyl]benzene 
• 5292-47-7 1,4-dimethyl 2-fluorobenzene-1,4-dicarboxylate 

Downstream Products

• 875222-54-1 4-(difluoromethyl)-2-fluorobenzaldehyde 
• 1270981-54-8 methyl 4-(difluoromethyl)-2-fluorobenzoate 
• 85070-58-2 methyl 2-fluoro-4-formylbenzoate 
• 1283718-57-9 methyl 2-fluoro-4-(hydroxymethyl)benzoate 
• 477199-77-2 4-(bromomethyl)-2-fluorobenzoic acid 
• 214554-23-1 4-((E)-2-Ethoxycarbonyl-vinyl)-2-fluoro-benzoic acid benzyl ester 
• 214554-25-3 4-(2-Ethoxycarbonyl-ethyl)-2-fluoro-benzoic acid 
• 214554-39-9 2-Fluoro-4-formyl-benzoic acid benzyl ester 
• 214554-37-7 3-(3-Fluoro-4-hydroxymethyl-phenyl)-propionic acid ethyl ester 
• 214554-20-8 2-Fluoro-4-hydroxymethyl-benzoic acid benzyl ester 

Relevant academic research and scientific papers

Fluoro- or trifluoromethyl-substituted benzyl and phenethyl alcohols: Substrates for metal-mediated site-selective functionalization

It was possible to functionalize the three fluorobenzyl alcohols and the three 2-(fluorophenyl)ethanols by metalation and subsequent carboxylation, the prototype electrophilic trapping reaction. Triisopropylsilyl (TIPS) outperformed methoxymethyl (MOM) as an O-protective group making seven new fluorobenzoic acids accessible in 63% average yield. Moreover, the TIPS group tolerates weakly basic and acidic media and, therefore, may facilitate further structural elaboration. The unprotected alcohols reacted more sluggishly and were unable to provide two of the targeted products (acids 1 and 2). The yield averaged only 46% in the five other cases (acids 3-7). The direct metalation of fluorinated benzyl and phenethyl alcohols remains nevertheless an attractive option because of its operational simplicity. All three (trifluoromethyl)benzyl alcohols and two of the three (trifluoromethyl)phenethyl alcohol isomers were successfully submitted to the metalation/functionalization sequence. These five starting materials gave rise to a total of nine new benzoic acids or lactones (compounds 8-14 and 17-18). Despite the poor yields (31% on average), the organometallic methods employed are, in general, extremely selective, economical and easy to perform. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Fluorinated linkers for monitoring solid-phase synthesis using gel- phase 19F NMR spectroscopy

Three fluorinated linkers which are analogues of linkers commonly used in solid-phase peptide synthesis have been prepared. Using 19F NMR spectroscopy, the fluorine atom of the linker allowed monitoring of several transformations in the solid-phase synthesis of a peptoid having a coumarin moiety. Especially, attachment of the linker to the solid phase, coupling of the first building block to the linker and cleavage of the product were efficiently monitored and optimised.