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
• Article Data: 19

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

Chemical Properties

white to light yellow crystal powder

Uses

2,4,5-Trifluorobenzoic Acid is a useful synthetic intermediate. It can be used to synthesize quinolone antibacterial agnts.

Synthesis Reference(s)

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

General Description

2,4,5-Trifluorobenzoic acid is an important quinolone antibacterial intermediate.

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

• 98349-22-5 2,4,5-trifluorobenzonitrile 
• 32890-92-9 2,3,4,6-tetrafluorobenzoic acid 
• 2367-82-0 1,2,3,5-tetrafluorobenzene 
• 367-23-7 1,2,4-trifluorobenzene 
• 129604-31-5 2,4,5-trifluoro-α-chloroacetophenone 
• 292621-58-0 3-chloro-2,4,5,6-tetrafluorobenzoyl chloride 
• 5360-81-6 3-chloro-2,4,5,6-tetrafluorobenzoic acid 
• 165047-24-5 2,4,5-trifluorobenzaldehyde 
• 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 
• 101513-67-1 2,4,5-trifluorobenzoyl fluoride 

Downstream Products

• 130137-04-1 2-(2,4-difluorophenylamino)-4,5-difluorobenzoic acid 
• 20372-66-1 methyl 2,4,5-trifluorobenzoate 
• 181821-02-3 2-(4-Dimethylamino-2,5-difluoro-phenylmethanesulfinyl)-N-pyridin-4-yl-nicotinamide 
• 181819-74-9 (4-Dimethylamino-2,5-difluoro-phenyl)-methanol 
• 181824-36-2 4-Dimethylamino-2,5-difluoro-benzoic acid methyl ester 
• 181824-00-0 2-(4-Dimethylamino-2,5-difluoro-benzylsulfanyl)-nicotinic acid 
• 181823-14-3 2-(4-Dimethylamino-2,5-difluoro-benzylsulfanyl)-N-pyridin-4-yl-nicotinamide 
• 182875-05-4 tert-butyl 2,4,5-trifluorobenzoate 
• 1355488-90-2 4-((5-chloro-6-isopropoxypyridin-3-yl)methoxy)-2,5-difluorobenzoic acid 
• 1355488-89-9 4-((5,6-dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoic acid 
• 1355488-86-6 tert-butyl 4-((5,6-dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoate 
• 1355488-61-7 4-[(5-chloropyridin-2-yl)methoxy]-2,5-difluoro-N-(methylsulfonyl)benzamide diethylamine salt 
• 1355063-61-4 4-(5-chloro-6-methoxypyridin-3-yloxy)-N-(cyclopropylsulfonyl)-2,5-difluorobenzamide diethylamine salt 
• 1355066-47-5 tert-butyl 4-{[5-chloro-6-(tetrahydro-2H-pyran-4-yloxy)pyridin-3-yl]oxy}-2,5-difluorobenzoate 

Relevant articles and documents

Hydrogen Bond Directed Photocatalytic Hydrodefluorination and Methods of Use Thereof

Methods of synthesizing compounds comprising fluorinated aryl groups are disclosed, wherein said methods utilize hydrogen bond directed photocatalytic hydrodefluorination.

Electrophilicity and nucleophilicity of commonly used aldehydes

The present approach for determining the electrophilicity (E) and nucleophilicity (N) of aldehydes includes a kinetic study of KMNO4 oxidation and NaBH4 reduction of aldehydes. A transition state analysis of the KMNO4 promoted aldehyde oxidation reaction has been performed, which shows a very good correlation with experimental results. The validity of the experimental method has been tested using the experimental activation parameters of the two reactions. The utility of the present approach is further demonstrated by the theoretical versus experimental relationship, which provides easy access to E and N values for various aldehydes and offers an at-a-glance assessment of the chemical reactivity of aldehydes in various reactions. the Partner Organisations 2014.

Fragmentation of radical anions of polyfluorinated benzoates

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.