653-21-4

Usage

Uses

Used in Chemical Synthesis:
2,3,4,5,6-PENTAFLUOROPHENYLACETIC ACID is used as a key intermediate in the synthesis of various organic compounds for different applications.
Used in Pharmaceutical Industry:
2,3,4,5,6-PENTAFLUOROPHENYLACETIC ACID is used as a building block for the development of pharmaceutical compounds, particularly in the synthesis of novel drugs with potential therapeutic applications.
Used in Agrochemical Industry:
2,3,4,5,6-PENTAFLUOROPHENYLACETIC ACID is used as a precursor in the production of agrochemicals, such as pesticides and herbicides, due to its ability to form stable and effective molecules.
Used in Material Science:
2,3,4,5,6-PENTAFLUOROPHENYLACETIC ACID is used as a component in the development of advanced materials, including polymers and coatings, that exhibit unique properties such as enhanced stability and resistance to environmental factors.
In the preparation of:
2,3,4,5,6-PENTAFLUOROPHENYLACETIC ACID is used in the preparation of 2,3,4,5,6-pentafluorophenylacetyl chloride, which serves as a valuable reagent in various chemical reactions and the synthesis of a wide range of organic compounds.
2,3,4,5,6-PENTAFLUOROPHENYLACETIC ACID is also used in the preparation of 4-bromo-phenacyl-2,3,4,5,6-pentafluorophenyl acetate, which is an important intermediate in the synthesis of complex organic molecules with potential applications in various industries.

InChI:InChI=1/C8H3F5O2/c9-4-2(1-3(14)15)5(10)7(12)8(13)6(4)11/h1H2,(H,14,15)/p-1

Upstream product

• 124-38-9 carbon dioxide 
• 1765-40-8 (bromomethyl)pentafluorobenzene 
• 653-30-5 (pentafluorophenyl)acetonitrile 
• 344-04-7 bromopentafluorobenzene 
• 653-37-2 perfluorobenzaldehyde 
• 653-35-0 2,3,4,5,6-pentafluorobenzyl chloride 
• 1582-05-4 diethyl 2-(perfluorophenyl)malonate 
• 440-60-8 (2,3,4,5,6-pentafluorophenyl)methanol 
• 827-15-6 1,2,3,4,5-pentafluoro-6-iodobenzene 
• 771-56-2 2,3,4,5,6-pentafluorotoluene 

Downstream Products

• 91407-87-3 pentafluorophenyldichloroacetyl chloride 
• 653-20-3 2.3.4.5.6-Pentafluor-phenylacetamid 
• 2260-89-1 2.3.4.5.6-Pentafluor-phenylessigsaeure-(4-brom-phenacylester) 
• 103067-97-6 (E)-β-(dimethylamino)-2,3,4,5,6-pentafluorostyrene 
• 103025-40-7 2-(pentafluorophenyl)-3-(dimethylamino)acrolein 
• 653-31-6 2-(pentafluorophenyl)ethanol 
• 832-72-4 2,3,4,5,6-pentafluorophenylacetyl chloride 
• 2412-72-8 2-Pentafluorophenylethyl bromide 
• 151228-81-8 Ag⁽¹⁺⁾*C₈H₂F₅O₂^(1-) 
• 178869-58-4 triphenyltin pentafluorophenylacetate 
• 853-74-7 2,2',3,3',4,4',5,5',6,6'-decafluorodibenzyl 
• 1235490-61-5 C₂₀H₂₆F₅N₂O₁₀P 
• 949260-75-7 2-(2-(perfluorophenyl)acetamido)thiophene-3-carboxamide 
• 934216-23-6 1-(dimethylamino)-3-(dimethyliminio)-2-(pentafluorophenyl)prop-1-ene perchlorate 

Relevant academic research and scientific papers

On the hydrolysis of diethyl 2-(perfluorophenyl)malonate

Diethyl 2-(perfluorophenyl)malonate was synthesized in 47% isolated yield by the reaction of sodium diethyl malonate and hexafluorobenzene. The resulting compound was considered as a starting material for synthesizing 2-(perfluorophenyl)malonic acid by hydrolysis. It was found that the desired 2-(perfluorophenyl)malonic acid could not be obtained from this ester by hydrolysis, neither under basic nor under acidic conditions. Nevertheless, hydrolysis of the ester with a mixture of HBr and AcOH gave 2-(perfluorophenyl)acetic acid in a good preparative yield of 63%. A significant advantage of this new approach to 2-(perfluoro-phenyl)acetic acid is that handling toxic substances such as cyanides and perfluorinated benzyl halides is avoided.

Solvent isotope effect on the hydroxide-ioncatalyzed hydration of ketenes in aqueous solution

Five ketenes, phenyl(ethyl)ketene, phenyl(methylthio)ketene, diphenylketene, pentafluorophenylketene, and 1-naphthylketene, were generated flash photolytically and solvent isotope effects (H2O vs. D2O) on their hydroxide-ioncatalyzed hydration in aqueous solution were determined. The values obtained are all weakly reverse and closely similar (k(HO)/k(DO) = 0.76-0.97), as expected for these fast, hydroxide-ion-consuming reactions, known to proceed by nucleophilic attack of hydroxide on the ketene carbonyl group. The characteristic magnitude of these isotope effects should prove useful in identifying new examples of this reaction.

Mechanism and Mechanism-Based Inactivation of 4-Hydroxyphenylpyruvate Dioxygenase

Six substrate analogs of 4-hydroxyphenylpyruvate, specifically pentafluorophenylpyruvate, 4-hydroxytetrafluorophenylpyruvate, 2-thienylpyruvate, 3-thienylpyruvate, thiophenol oxalate, and p-thiocresol oxalate were synthesized and their interactions with porcine liver 4-hydroxyphenylpyruvate dioxygenase investigated.Both pentafluorophenylpyruvate and thiophenol oxalate are competitive inhibitors of the enzyme with K1 values of 14 and 150 μM, respectively, but p-thiocresol oxalate has no effect on the enzymic activity.The other three substrate analogs are both substrates and mechanism-based inactivators of the enzyme with the following kinetic characteristics (compound, Km, Vmax,kinact, K', partition ratio) at pH 6.0, 37 deg C, and an air atmosphere: 4-hydroxytetrafluorophenylpyruvate, 50 μM, 1.9 mkat/kg, 1.5/min, 70 μM, 4.2; 2-thienylpyruvate, 500μM, 7.8 mkat/kg, 0.6/min, 400 μM, 41; 3-thienylpyruvate, 250 μM, 2.9 mkat/kg, 0.6/min, 300 μM, 22.When inactivated, the dioxygenase was found to contain per mole of active enzyme, 0.78 mol of label from 3-thienyl-3pyruvate and 0.85 mol of label from 4-hydroxytetrafluorophenyl-3pyruvate.The product formed from the enzyme-catalyzed oxidation of 3-thienylpyruvate was determined to be 3-carboxymethyl-3-thiolene-2-one.The implication of these results to the mechanism of the dioxygenase is considered.