446-17-3

Basic information

• Product Name: 2,4,5-Trifluorobenzoic acid
• Synonyms: RARECHEM AL BO 0258;2,4-trifluorobenzoic acid and derivatives;2,4,5-Trilfuorobenzoic acid;2,4,5-TRIFLUOROBENZOIC ACID AND THE DERIVATIVES;2,4,5-TrifluoroBenzoicacidsolution;2,4,5-Trifluorobenzoic acid, 99.5+%;2,4,5-Trifluorobenzoic acid 20% solution;2,4,5-Trifluorobenzoic acid 99%
• CAS NO: 446-17-3
• Molecular Formula: C₇H₃F₃O₂
• Molecular Weight: 176.09
• EINECS: 1308068-626-2
• Product Categories: blocks;Carboxes;FluoroCompounds;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Miscellaneous;C7;Carbonyl Compounds;Carboxylic Acids;Pyridines ,Halogenated Heterocycles
• Mol File: 446-17-3.mol

Chemical Properties

• Melting Point: 94-96 °C(lit.)
• Boiling Point: 241.9 °C at 760 mmHg
• Flash Point: 100.1 °C
• Appearance: white to light yellow crystal powder
• Density: 1.4362 (estimate)
• Vapor Pressure: 0.0188mmHg at 25°C
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 2.87±0.10(Predicted)
• BRN: 3257609
• CAS DataBase Reference: 2,4,5-Trifluorobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,5-Trifluorobenzoic acid(446-17-3)
• EPA Substance Registry System: 2,4,5-Trifluorobenzoic acid(446-17-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 446-17-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,4,5-Trifluorobenzoic acid is used as a synthetic intermediate for the production of quinolone antibacterial agents. It plays a crucial role in the synthesis of these medications due to its unique chemical properties, which allow for the development of effective treatments against various bacterial infections.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2,4,5-Trifluorobenzoic acid serves as a valuable building block for creating a range of fluorinated compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science. Its trifluoromethylated structure endows it with unique reactivity and properties, making it a versatile starting material for further chemical transformations.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 34, p. 168, 1991 DOI: 10.1021/jm00105a025

InChI:InChI=1/C7H3F3O2/c8-4-2-6(10)5(9)1-3(4)7(11)12/h1-2H,(H,11,12)/p-1

Upstream product

• 327-52-6 1-bromo-2,4,5-trifluorobenzene 
• 124-38-9 carbon dioxide 
• 129322-83-4 2',4',5'-trifluoroacetophenone 
• 456-22-4 4-Fluorobenzoic acid 
• 292621-58-0 3-chloro-2,4,5,6-tetrafluorobenzoyl chloride 
• 5360-81-6 3-chloro-2,4,5,6-tetrafluorobenzoic acid 
• 117-08-8 tetrachlorophthalic anhydride 
• 33795-85-6 N-methyl-tetrafluorophthalimide 
• 14737-80-5 N-methyl-tetrachlorophthalimide 
• 72524-66-4 3,4,6-trichloro-N-methylphthalimide 
• 62268-16-0 3,4,6-trichlorophthalic acid 
• 129604-31-5 2,4,5-trifluoro-α-chloroacetophenone 
• 101513-67-1 2,4,5-trifluorobenzoyl fluoride 
• 104222-42-6 3-bromo-2,4,5-trifluorobenzoic acid 

Downstream Products

• 88419-56-1 2,4,5-trifluorobenzoyl chloride 
• 351354-41-1 ethyl 2,4,5-trifluorobenzoate 
• 223444-95-9 N-t-Butyl-2,4,5-trifluorobenzamide 
• 125290-71-3 N-(2-Hydroxy-1,1-dimethylethyl)-2,4,5-trifluorobenzamide 
• 367-23-7 1,2,4-trifluorobenzene 
• 101513-77-3 3-Chloro-2,4,5-trifluorobenzoic acid 
• 20372-66-1 methyl 2,4,5-trifluorobenzoate 
• 391212-00-3 4,5-difluoro-2-[(2-fluoro-4-iodophenyl)amino]benzoic acid 
• 1160749-42-7 C₉H₇F₃N₄O 
• 1354963-02-2 2,5-difluoro-4-hydroxy-N-(methylsulfonyl)benzamide 
• 1354955-39-7 4-(4-Chloro-2-ethylphenoxy)-2,5-difluoro-N-(methylsulfonyl)benzamide 
• 1354960-56-7 4-(2-cyanophenoxy)-2,5-difluoro-N-(methylsulfonyl)benzamide 
• 1078132-91-8 2,5-difluoro-4-(2-propynyloxy)benzoic acid 2-propynyl ester 
• 1133810-47-5 methyl-(2S)-2-(1-hydroxy-3-oxo-1,3-dihydroisoindol-2-yl)-2-[8-(2,4,5-trifluorobenzoyl)-8-aza-bicyclo[3.2.1]-oct-3-yl]-exo-acetate 

Relevant articles and documents

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Hydrogen Bond Directed Photocatalytic Hydrodefluorination: Overcoming Electronic Control

The photocatalytic C-F functionalization of highly fluorinated arenes is a powerful method for accessing functionalized multifluorinated arenes. The decisive step in the determining regioselectivity in fluorine functionalization is fluoride fragmentation from the radical anion of the multifluorinated arene. To date, the availability of regioisomers has been dictated by the innate electronics of the fluorinated arene, limiting the synthetic utility of the chemistry. This study investigates the remarkable ability of a strategically located hydrogen bond to transcend the normal regioselectivity of the C-F functionalization event. A significant rate acceleration is additionally observed for hydrodefluorination of fluorines that can undergo intramolecular hydrogen bonds that form 5-8-membered cycles with moderately acidic N-H's. The hydrogen bond is expected to facilitate the fragmentation not only by bending the C-F bond of the radical anion out of planarity but also by increasing the exothermicity of the fluoride extrusion step through protonation of the naked fluoride. Finally, the synthetic utility of the method is demonstrated in an expedited synthesis of the trifluorinated α-phenyl acetic acid derivative required for the commercial synthesis of Januvia, an antidiabetic drug. This represents the first synthesis of a commercially important multifluorinated arene via a defluorination strategy and is significantly shorter than the current strategy.

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INHIBITORS OF STEAROYL-COA DESATURASE

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A comprehensive study of the symmetry forbidden fragmentation of short-lived radical anions (RAs) has been undertaken for the complete set of polyfluorinated benzoates (C6FnH5-nCO22, n = 1-5). The decay rate constants (kc) of RAs have been determined in aqueous alkaline solution (pH 13.4) by electron photoinjection (EPI) from mercury electrodes and were found to increase dramatically from ≤3 × 103 s-1 (3-F - C6H4CO2-) to (1.2 ± 0.8) × 109 s-1 (C6F5CO2-). The regioselectivity of C-F bond cleavage in the RA fragmentation has been revealed by structure assignment of reduction products of the polyfluorinated benzoic acids by Na, K, and Zn in liquid NH3, as well as by Zn in aqueous NH3 and aqueous alkaline solutions. The kc values depend on the position of the cleaved fluorine to the CO2- group generally in the order para > ortho > meta, and to sharply increase if adjacent fluorine atoms are present. The observed trends reveal that the kinetics of the RA fragmentation reaction is not controlled by the reaction thermodynamics. Semiempirical UHF/INDO calculations, the validity of which has been confirmed by ab initio ROHF/6-31+G calculations, were done to rationalize the observed trends. The reaction transition state (TS) was considered to arise from the RA's and 2*states crossing avoided due to out-of-plane deviation of the cleaving C-F bond. The satisfactory linear correlation (R = 0.96) between the model reaction energy barrier Ea and log kc has been achieved with modeling the local solvation of the CO2- group by its protonation.

Process improvements in the synthesis of 2,4,5-trifluorobenzoic acid. selective hydrodefluorination of tetrafluorophthalimides

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Spiro compound

The present invention relates to spiro compounds of general formula I: STR1 wherein the substituents are herein below defined. The present invention relates to antibacterial spiro compounds which are of value as drugs for humans, veterinary drugs or drugs for use in fish culture or as preservatives, and to antibacterial compositions containing one or more of the same compounds as active ingredients.