36629-42-2

Usage

Uses

Used in Photocoupling Applications:
Methyl Pentafluorobenzoate is used as a key component in the preparation of photocoupling agents. It is particularly useful for the efficient immobilization of polymers, nanoparticles, graphene, and small molecules. Its chemical structure allows for strong interactions with these materials, enhancing their stability and functionality.
Used in Photoactive Reagent Preparation:
Methyl Pentafluorobenzoate is also employed in the preparation of photoactive reagent N-hydroxysuccinimide (NHS)-PFPA. This reagent is valuable in various chemical reactions, particularly in the field of biochemistry and pharmaceuticals, where it can be used for the conjugation of molecules to create new compounds with specific properties.
Used in Chemical Synthesis:
In the chemical synthesis industry, Methyl Pentafluorobenzoate serves as an important intermediate for the production of various compounds. Its unique structure and reactivity make it a versatile building block for creating a wide range of molecules with different applications.
Used in Material Science:
Methyl Pentafluorobenzoate is utilized in the development of new materials with specific properties, such as improved stability, reactivity, or functionality. Its incorporation into polymers, nanoparticles, and other materials can enhance their performance in various applications, including electronics, coatings, and adhesives.

InChI:InChI=1/C8H3F5O2/c1-15-8(14)2-3(9)5(11)7(13)6(12)4(2)10/h1H3

Upstream product

• 67-56-1 methanol 
• 602-94-8 Pentafluorobenzoic acid 
• 2251-50-5 pentafluorobenzoylchloride 
• 64-17-5 ethanol 
• 4522-93-4 ethyl pentafluorobenzoate 
• 811-98-3 d⁽⁴⁾-methanol 
• 108-24-7 acetic anhydride 
• 879-06-1 pentafluorophenylmagnesium chloride 
• 201157-00-8 pentafluorobenzoylfluoride dimethyl acetal 
• 3070-53-9 1,6-heptadiene 
• 201157-01-9 1,2,3,4,5-Pentafluoro-6-trimethoxymethyl-benzene 

Downstream Products

• 201157-01-9 1,2,3,4,5-Pentafluoro-6-trimethoxymethyl-benzene 
• 122590-75-4 methyl 4-azidotetrafluorobenzoate 
• 122590-83-4 methyl N-(4-methylphenyl)-4-aminotetrafluorobenzoate 
• 122590-84-5 methyl N-(2-methylphenyl)-4-aminotetrafluorobenzoate 
• 122590-82-3 methyl N-benzyl-4-amino-2,3,5,6-tetrafluorobenzoate 
• 41714-44-7 Methyl-2,3,4,5-tetrafluor-6-phenylbenzoat 
• 1190369-97-1 4,5,6,7-tetrafluoro-1H-indazole-3-ol 
• 1093346-60-1 4-azido-2,3,5,6-tetrafluoro-N-(2-(2-(2-hydroxyethoxy)ethoxy)ethyl)benzamide 
• 1265905-73-4 2-(2-(2-(-4-azido-2,3,5,6-tetrafluorobenzamido)ethoxy)ethoxy)ethyl 2-bromo-2-methylpropanoate 
• 1190369-96-0 3-pentafluorophenyl-4,5,6,7-tetrafluoro-1H-indazole 
• 853-39-4 bis(pentafluorophenyl)-methanone 
• 1545-58-0 1-(2,4-dinitrophenyl)-2-((perfluorophenyl)methylene)hydrazine 
• 17413-01-3 pentafluorobenzohydrazide 
• 1156836-27-9 C₈HF₅N₂OS 

Relevant academic research and scientific papers

Study of Pd-elimination under carbonylation conditions: Regioselective formation of esters

The regioselective synthesis of methyl esters is achieved by carbonylation of two different types of organometallic derivatives resulting from insertion of non-conjugated dienes into a Pd-aryl bond. When the diene and the Pd-aryl synthon [PdPfBr(NCMe)2] (Pf = C6F5) are mixed at low temperature, solutions of η1-η2-enylpalladium complexes can be isolated and converted into β-aryl methyl esters by reaction with CO in the presence of methanolic solutions of sodium methoxide. When the reactions are carried out at room temperature η3-allylpalladium complexes are isolated, and their carbonylation gives β,γ-unsaturated esters.

DERIVATIVES OF AN FGFR INHIBITOR

The present disclosure relates to derivatives (e.g., hydroxyl, keto, glucuronide, sulfonic acid, and deuterated) of a Fibroblast Growth Factor Receptors (FGFR) inhibitor, including methods of preparation thereof, and intermediates in the preparation thereof, which are useful in the treatment of FGFR mediated disease such as cancer.

SOLID FORMS OF AN FGFR INHIBITOR AND PROCESSES FOR PREPARING THE SAME

The present disclosure relates to 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-1,3,4,7-tetrahydro-2H-pyrrolo[3',2':5,6]pyrido[4,3-d]pyrimidin-2-one, solid forms and polymorphs thereof, methods of preparation thereof, and intermediates in the preparation thereof, which are useful in the treatment of the FGFR-associated or mediated diseases such as cancer.

Synthesis and evaluation of some substituted heterocyclic fluconazole analogues as antifungal agents

A new series of fluconazole analogues of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4- difluoro-phenyl)-3-4-(substituted-heterocyclic ring-1H-1,2,3- triazol-1-yl)-2-propanols (1-10) were designed, synthesized and evaluated as antifungal agents. Preliminary antifungal tests showed that most of the title compounds exhibited moderate activity with broad spectrum against eight human pathogenic fungi in vitro, compounds 1 and 6 had the best antifungal activity against Candida albicans with the value of MIC80 = 0.5 μg/mL respectively.

Photocatalytic hydrodefluorination: Facile access to partially fluorinated aromatics

Polyfluorinated aromatics are essential to materials science as well as the pharmaceutical and agrochemical industries and yet are often difficult to access. This Communication describes a photocatalytic hydrodefluorination approach which begins with easily accessible perfluoroarenes and selectively reduces the C-F bonds. The method allows facile access to a number of partially fluorinated arenes and takes place with unprecedented catalytic activity using a safe and inexpensive amine as the reductant.

Synthesis of photoreactive phosphatidic acid analogues displaying activatory properties on cyclic AMP-phosphodiesterases. Photoaffinity labeling of an isoform of phosphodiesterase

We have previously shown that phosphatidic acid (PA) is a specific activator of some isoforms of type 4 cyclic nucleotide phosphodiesterases (PDE 4) and that accumulation of endogenous PA can, in this way, influence the cAMP signaling pathway in different cell types. Enzyme activation depends on direct binding of the effector to specific sites carried by the enzyme. To identify the binding domain, photoactivatable phosphatidic acid analogues 1-azidoPA (12) and 2-azidoPA (7 and 15), potentially suitable for covalent labeling of PDE4, have been synthesized. The ability of phospholipases A2 and D to hydrolyze unnatural phospholipids has been considered in this paper. The effect of 1-azidoPA (12) and 2-azidoPA (7 and 15) on the activity of a recombinant PA-sensitive isoform PDE4D3 was evaluated. The three compounds were able to activate the enzyme with different efficiencies. A tritiated analogue of 15 was synthesized and used in PDE4D3 labeling experiments, which showed that this PA analogue was specifically and covalently linked to the enzyme after UV irradiation. Photoactivatable analogues thus appear as suitable tools for the characterization of PA binding sites.

Nucleophilic aromatic substitution with dialkoxycarbenes

Dimethoxycarbene, generated at 110°C by thermolysis of 2,2-dimethoxy-5,5-dimethyl-Δ3-1,3,4-oxadiazoline, displaces fluoride from aromatic rings that are activated with electron-withdrawing groups. Intermolecular substitution on Sanger's reagent and on hexafluorobenzene are reported, together with intramolecular substitution by a dioxycarbene with a tethered aryl group.

New Reagents for Photoaffinity Labeling: Synthesis and Photolysis of Functionalized Perfluorophenyl Azides

Functionalized perfluorophenyl azides (PFPA) 2-6, 8-12, 14-19, and 21-29 were synthesized, allowing the attachment of PFPA to other molecules for application as photolabels.Two biactive molecules were modified by a PFPA as potential photoaffinity labeling reagents.Photolysis of two representative members was investigated.Photolysis of azide 4 in cyclohexane gave 57 percent of CH insertion product.When photolysis was carried out in the presence of diethylamine as a trapping reagent, it gave 65 percent of NH insertion product, and no ring expansion product was found.The nitro azide 19 showed a shoulder absorption in the longer wavelength compared to azide 4.Azide 19 gave less CH insertion and more aniline products compared to azide 4 when photolyzed in toluene, suggesting that the nitro group accelerates intersystem crossing of the singlet nitrene or the singlet excited azide.Collectively, our results demonstrate that the functionalized PFPA investigated are much better in undergoing CH insertion than their nonfluorinated analogues and suggest that they may constitute an improved series of photolabeling reagents.

Oxiranes from Methylenation of the Ester Carbonyl Group by Diazomethane

Esters suitably substituted by electronegative groups were found to react with diazomethane with the anchimeric assistance of a ?-system or a trifluoromethyl group close to the ester oxygen to yield 2-alkoxy-2-substituted-oxiranes in good to excellent yields without catalysts.