84376-20-5

Usage

Uses

Used in Pharmaceutical Industry:
3,5-DIFLUORO-2-HYDROXY-BENZOIC ACID is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to enhance the biological activity and pharmacokinetic properties of drug molecules. Its unique structure allows for the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
3,5-DIFLUORO-2-HYDROXY-BENZOIC ACID is utilized as a building block in the synthesis of agrochemicals, contributing to the development of novel pesticides and herbicides. Its incorporation into these compounds can lead to enhanced crop protection and increased agricultural productivity.
Used in Material Science:
3,5-DIFLUORO-2-HYDROXY-BENZOIC ACID is employed in the development of new materials, such as polymers and coatings, due to its chemical properties and reactivity. Its fluorinated structure can impart unique characteristics to these materials, including improved stability, durability, and resistance to environmental factors.
Used in Medicinal Chemistry Research:
3,5-DIFLUORO-2-HYDROXY-BENZOIC ACID is used as a research compound in medicinal chemistry to explore its potential as a therapeutic agent or as a structural component in the design of new drugs. Its unique properties and reactivity make it a valuable tool for understanding the structure-activity relationships in drug discovery.

InChI:InChI=1/C7H4F2O3/c8-3-1-4(7(11)12)6(10)5(9)2-3/h1-2,10H,(H,11,12)

Upstream product

• 367-27-1 2,4-difluorophenol 
• 654-87-5 2,3,5-trifluorobenzoic acid 
• 749230-34-0 2-chloro-1,3-difluoro-4-(methoxymethoxy)benzene 
• 210350-62-2 1,3-difluoro-4-(methoxymethoxy)benzene 
• 140675-42-9 (3,5-difluoro-2-hydroxy-phenyl)-ethanone 
• 749230-36-2 4-chloro-3,5-difluoro-2-hydroxybenzoic acid 
• 63954-77-8 3,5-difluorosalicylaldehyde 

Downstream Products

• 180068-67-1 methyl 3,5-difluorosalicylate 
• 1017779-70-2 2-ethoxy-3,5-difluoro-benzoic acid 
• 1444116-27-1 2-ethoxy-3,5-difluoro-benzoic acid ethyl ester 

Relevant academic research and scientific papers

PYRROLOMYCINS AND METHODS OF USING THE SAME

Provided herein are pyrrolomycin derivatives, which can be used to modulate Mcl-1, inhibit proliferation of bacteria and pathogens, as well as to treat infectious diseases and cancers.

Novel fluorinated pyrrolomycins as potent anti-staphylococcal biofilm agents: Design, synthesis, pharmacokinetics and antibacterial activities

Staphylococcus aureus (SA) is a major cause of hospital- and community-associated bacterial infections in the U.S. and around the world. These infections have become increasingly difficult to treat due to the propensity to develop antibiotic resistance and form biofilm. To date, no antibiofilm agents are available for clinical use. To add to the repertoire of antibiotics for clinical use and to provide novel agents for combating both SA and biofilm infections, we previously reported marinopyrroles as potent anti-SA agents. In this study, we used fragment-based and bioisostere approaches to design and synthesize a series of novel fluorinated pyrrolomycins for the first time, performed analyses of their physicochemical and drug-like properties, and investigated structure activity relationships and pharmacokinetics. These promising fluorinated pyrrolomycins demonstrate potent antibacterial activity against SA with favorable drug-like properties and pharmacokinetic profiles. Importantly, these compounds kill staphylococcal biofilm-associated cells with a lack of mammalian cell cytotoxicity and no occurrence of bacterial resistance. Our novel fluorinated pyrrolomycin 4 has a clogP value of 4.1, an MIC of 73 ng/mL, MBC of 4 μg/mL, kill staphylococcal-associated biofilm at 8 μg/mL, bioavailability of 35%, and the elimination half-life of 6.04 h and 6.75 h by intravenous and oral administration, respectively. This is the first report of comprehensive drug discovery studies on pyrrolomycin-based antibiotics.

Salicylate activity. 3. Structure relationship to systemic acquired resistance

Salicylic acid (2-hydroxybenzoic acid; SA) is a primary signal inducing plant defenses against pathogens. This plant disease resistance, known as systemic acquired resistance (SAR), is an attractive target for the development of new plant protection agents. SAR induction is a multistep process that includes accumulation of pathogenesis-related (PR) proteins. The structure-activity profile of salicylates and related compounds has been evaluated using an inducible PR protein (PR-1a) and plant resistance to tobacco mosaic virus (TMV) as markers. Among the 47 selected monosubstituted and multiple-substituted salicylate derivatives tested, all 8 derivatives that induced more PR-1a protein than SA were fluorinated or chlorinated in the 3- and/or 5-position (3,5-difluorosalicylate > 3-chlorosalicylate > 5-chlorosalicylate > 3,5-dichlorosalicylate > 3-chloro-5-fluorosalicylate > 3-fluorosalicylate > 3-fluoro-5-chlorosalicylate > 3,5-dichloro-6-hydroxysalicylate > SA). In general, substitutions for or on the 2-hydroxyl group or at the 4-position of the ring reduced or eliminated PR-1a protein induction. In contrast, substitutions in positions ortho (3-position) or para (5-position) to the hydroxyl group with electron-withdrawing groups other than chlorine or fluorine decreased induction, and electron-donating groups in these positions also had a deleterious effect on PR-1a induction. PR-1a protein accumulation and reduction in TMV lesion diameter exhibited a log-linear relationship. The seven salicylate derivatives that were the most active TMV resistance inducers were all halogenated in the 3- and/or 5-position (3-chlorosalicylate > 3,5-difluorosalicylate > 3,5-dichloro-6-hydroxysalicylate > 3,5,6-trichlorosalicylate > 5-chlorosalicylate > 5-fluorosalicylate > 3,5-dichlorosalicylate > 4-fluorosalicylate > 3-fluorosalicylate > 3-chloro-5-fluorosalicylate > 4-chlorosalicylate > SA). The correlation between PR-1a protein induction and resistance to TMV confirms the value of using PR-1a induction as a screening tool for developing new plant disease control agents.

The regioexhaustive functionalization of difluorophenols and trifluorophenols through organometallic intermediates

2,4-Difluorophenol, 2,5-difluorophenol, 2,3-difluorophenol, 3,5-difluorophenol, 3,4-difluorophenol, 2,4,5-trifluorophenol and 2,3,4-trifluorophenol were converted into all 18 possible di- or trifluorinated hydroxybenzoic acids (1a-c, 4a-c, 9a-c, 12a,b, 14a-c, 17a,b, 18a,b), all of them new compounds. The phenolic hydrogen atom was replaced by a methoxymethyl or, less frequently, by a triisopropylsilyl group, which exerted an ortho activating or ortho shielding effect, respectively. Sites flanked by two electronegative substituents (fluorine, alkoxy) were deprotonated with particular ease. They had to be silenced by the reversible attachment of a metalation-blocking trimethylsilyl group or of a metalation-deflecting chlorine atom if the metal was to be introduced elsewhere. In all cases but one, the stage was thus set for an intramolecular competition between metalation at an oxygen-adjacent or a fluorine-adjacent site. It proved indeed possible to secure the desired regioflexibility in either way by relying on an appropriate substrate-reagent matching. This demonstrates once more the potential of the organometallic approach to diversity-oriented synthesis.

An improved method for the preparation of 3,5-difluorosalicylaldehyde and 3,5-difluorosalicylic acid

An improved method for the synthesis of 3,5-difluorosalicylic acid (3b) and 3,5-difluorosalicylaldehyde (3a) is described. 2,4-Difluorophenol (4) undergoes a formylation reaction to afford aldehyde 3a which is oxidized to the desired acid 3b. This method