587-88-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Fluorophenylacetic acid ethyl ester is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its presence in the development process allows for the creation of drugs with analgesic and anti-inflammatory properties, making it a valuable component in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Fluorophenylacetic acid ethyl ester is utilized as a building block in the synthesis of agrochemicals. Its role in this industry is crucial for the development of products that can enhance crop protection and improve agricultural yields.
Used in Organic Chemistry:
4-Fluorophenylacetic acid ethyl ester is also used as a reagent in organic chemistry for the synthesis of more complex organic compounds. Its versatility in chemical reactions makes it an important tool for researchers and chemists working on the development of new organic molecules with potential applications in various fields.

InChI:InChI=1/C10H11FO2/c1-2-13-10(12)7-8-3-5-9(11)6-4-8/h3-6H,2,7H2,1H3

Upstream product

• 64-17-5 ethanol 
• 405-50-5 p-Fluorophenylacetic acid 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 332-29-6 2-(4-fluorophenyl)acetamide 
• 20511-20-0 ethyl p-methylcinnamate 
• 101-97-3 Ethyl 2-phenylethanoate 
• 150-46-9 triethyl borate 
• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 459-04-1 4-Fluorophenylacetyl chloride 
• 352-33-0 1-Chloro-4-fluorobenzene 
• 6148-64-7 ethyl potassium malonate 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 105-53-3 diethyl malonate 
• 1765-93-1 4-fluoroboronic acid 

Downstream Products

• 459-14-3 (4-fluoro-phenyl)-acetic acid-(2-hydroxy-ethylamide) 
• 798-59-4 tris-(4-fluoro-phenyl)-ethene 
• 104920-79-8 ethyl α-formyl-4-fluorophenylacetate 
• 100638-27-5 2-(4-fluorophenyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine 
• 137-07-5 2-amino-benzenethiol 
• 138507-01-4 3-(4-fluorophenyl)-4-hydroxy-1-(3-trifluoromethylphenyl)-1,8-naphthyridin-2-(1H)-one 
• 130754-17-5 ethyl 2-fluoro-2-(4-fluorophenyl)acetate 
• 175543-23-4 ethyl α,α-difluoro-α-(p-fluorophenyl)acetate 
• 208655-02-1 2-(4-fluorophenyl)-3-oxo-3-pyridin-4-ylpropionic acid ethyl ester 
• 208655-00-9 5-(4-fluorophenyl)-3-methyl-2-methylthio-6-(pyridin-4-yl)-3H-pyrimidin-4-one 
• 1026013-99-9 3-(6-chloro-pyridin-3-yl)-2-(4-fluoro-phenyl)-3-oxo-propionic acid ethyl ester 
• 2965-90-4 diethyl 2-(4-fluorophenyl)malonate 
• 742699-58-7 6-(4-methoxyphenyl)-4-(4-methylsulfanylphenyl)-3-(4-fluorophenyl)pyran-2-one 
• 742699-59-8 6-(4-ethoxyphenyl)-4-(4-methylsulfanylphenyl)-3-(4-fluorophenyl)pyran-2-one 

Relevant academic research and scientific papers

Copper-Catalyzed Ullmann-Type Coupling and Decarboxylation Cascade of Arylhalides with Malonates to Access α-Aryl Esters

We have developed a high-efficiency and practical Cu-catalyzed cross-coupling to directly construct versatile α-aryl-esters by utilizing readily available aryl bromides (or chlorides) and malonates. These gram-scale approaches occur with turnovers of up to 1560 and are smoothly conducted by the usage of a low catalyst loading, a new available ligand, and a green solvent. A variety of functional groups are tolerated, and the application occurs with α-aryl-esters to access nonsteroidal anti-inflammatory drugs (NSAIDs) on the gram scale.

Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment

Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.

Enantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning

Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral catalysts remains a challenge and highlights the need to identify new chemotypes for this purpose. Herein, the discovery and optimization of a bench-stable chiral 9-hydroxy-9,10-boroxarophenanthrene catalyst is described and applied in the highly enantioselective desymmetrization of 2-aryl-1,3-diols using benzylic electrophiles under operationally simple, ambient conditions. Nucleophilic activation and discrimination of the enantiotopic hydroxy groups on the diol substrate occurs via a defined chairlike six-membered anionic complex with the hemiboronic heterocycle. The optimal binaphthyl-based catalyst 1g features a large aryloxytrityl group to effectively shield one of the two prochiral hydroxy groups on the diol complex, whereas a strategically placed "methyl blocker"on the boroxarophenanthrene unit mitigates the deleterious effect of a competing conformation of the complexed diol that compromised the overall efficiency of the desymmetrization process. This methodology affords monoalkylated products in enantiomeric ratios equal or over 95:5 for a wide range of 1,3-propanediols with various 2-aryl/heteroaryl groups.

2-(Halogenated Phenyl) acetamides and propanamides as potent TRPV1 antagonists

A series consisting of 117 2-(halogenated phenyl) acetamide and propanamide analogs were investigated as TRPV1 antagonists. The structure–activity analysis targeting their three pharmacophoric regions indicated that halogenated phenyl A-region analogs exhibited a broad functional profile ranging from agonism to antagonism. Among the compounds, antagonists 28 and 92 exhibited potent antagonism toward capsaicin for hTRPV1 with Ki[CAP] = 2.6 and 6.9 nM, respectively. Further, antagonist 92 displayed promising analgesic activity in vivo in both phases of the formalin mouse pain model. A molecular modeling study of 92 indicated that the two fluoro groups in the A-region made hydrophobic interactions with the receptor.

Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide-Functionalized Phosphine Ligands

The coupling of aryl chlorides with Reformatsky reagents is a desirable strategy for the construction of α-aryl esters but has so far been substantially limited in the substrate scope due to many challenges posed by various possible side reactions. This limitation has now been overcome by the tailoring of ylide-functionalized phosphines to fit the requirements of Negishi couplings. Record-setting activities were achieved in palladium-catalyzed arylations of organozinc reagents with aryl electrophiles using a cyclohexyl-YPhos ligand bearing an ortho-tolyl-substituent in the backbone. This highly electron-rich, bulky ligand enables the use of aryl chlorides in room temperature couplings of Reformatsky reagents. The reaction scope covers diversely functionalized arylacetic and arylpropionic acid derivatives. Aryl bromides and chlorides can be converted selectively over triflate electrophiles, which permits consecutive coupling strategies.

Rapid Assembly of Saturated Nitrogen Heterocycles in One-Pot: Diazo-Heterocycle “Stitching” by N–H Insertion and Cyclization

Methods that provide rapid access to new heterocyclic structures in biologically relevant chemical space provide important opportunities in drug discovery. Here, a strategy is described for the preparation of 2,2-disubstituted azetidines, pyrrolidines, pi

Application of trivalent iodine compounds as catalysts in Bal-Schiemann reaction

The invention discloses an application of trivalent iodine compounds shown in formula I and/or II in the description and used as catalysts in Bal-Schiemann reaction. The trivalent iodine compounds areused as the catalysts in the Bal-Schiemann reaction, so that the Bal-Schiemann reaction can be conducted at room temperature or near room temperature when a thermochemical method is used, and the reaction has mild reaction conditions, wide substrate use range and short reaction time, and is safe and easy to operate, products are easy to separate, and raw materials are simple and low in toxicity.

Design, synthesis, insecticidal activity and 3D-QSR study for novel trifluoromethyl pyridine derivatives containing an 1,3,4-oxadiazole moiety

A series of trifluoromethyl pyridine derivatives containing 1,3,4-oxadiazole moiety was designed, synthesized and bio-assayed for their insecticidal activity. The result of bio-assays indicated the synthesized compounds exhibited good insecticidal activity against Mythimna separata and Plutella xylostella, most of the title compounds show 100% insecticidal activity at 500 mg L-1 and >80% activity at 250 mg L-1 against the two pests. Compounds E18 and E27 showed LC50 values of 38.5 and 30.8 mg L-1 against Mythimna separata, respectively, which were close to that of avermectin (29.6 mg L-1); compounds E5, E6, E9, E10, E15, E25, E26, and E27 showed 100% activity at 250 mg L-1, which were better than chlorpyrifos (87%). CoMFA and CoMSIA models with good predictability were proposed, which revealed the electron-withdrawing groups with an appropriate bulk at 2- and 4-positions of benzene ring could enhance insecticidal activity.

Hypervalent Iodine(III)-Catalyzed Balz–Schiemann Fluorination under Mild Conditions

An unprecedented hypervalent iodine(III) catalyzed Balz–Schiemann reaction is described. In the presence of a hypervalent iodine compound, the fluorination reaction proceeds under mild conditions (25–60 °C), and features a wide substrate scope and good functional-group compatibility.

Synthesis and Biological Activity of Anthranilic Diamide Derivatives Incorporating 1,3,4-oxadiazole or Nitrogen-containing Saturated Heterocyclic Moieties

A series of novel anthranilic diamide derivatives incorporating 1,3,4-oxadiazole or nitrogen-containing saturated heterocyclic moieties were synthesized, characterized, and evaluated for bacteriostatic activity against three phytopathogenic bacteria Xanthomonas oryzae pv. Oryzae (Xoo), Xanthomonas axonopodis pv. Citri (Xac), Ralstonia solanacearum (R. solanacearum). The preliminary biological results indicated that most compounds exhibit bacteriostatic activity against three phytopathogenic bacteria. Among these compounds, compounds 6g, 6f, and 6i displayed better antibacterial activity. In the test with concentration of 200 μg/mL, antibacterial activity of compound 6i and 6j was 96%. In particular, the bacteriostatic activity displayed by compound 6h against Xoo is similar to the one displayed by commercial drug bismerthiazol.