310-40-7

Usage

Uses

Used in Pharmaceutical Industry:
(4-FLUORO-PHENYL)-PHOSPHONIC ACID DIETHYL ESTER is used as a chemical intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, (4-FLUORO-PHENYL)-PHOSPHONIC ACID DIETHYL ESTER serves as a precursor for the production of agrochemicals, aiding in the creation of pesticides and other agricultural chemicals to protect crops and enhance yields.
Used in Organophosphorus Compounds Production:
(4-FLUORO-PHENYL)-PHOSPHONIC ACID DIETHYL ESTER is utilized as a precursor in the synthesis of other organophosphorus compounds, which have diverse applications in various industries, including chemical manufacturing and materials science.

Upstream product

• 462-06-6 fluorobenzene 
• 64723-95-1 pinacolone enolate anion 
• 352-34-1 4-fluoro-1-iodobenzene 
• 29800-93-9 diethyl phosphite 
• 762-04-9 phosphonic acid diethyl ester 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 122-52-1 triethyl phosphite 
• 814-49-3 diethyl chlorophosphate 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 1765-93-1 4-fluoroboronic acid 
• 824-80-6 sodium 4-fluorobenzenesulfinate 
• 371-40-4 4-fluoroaniline 
• 33715-53-6 triethoxy(4-fluorophenyl)silane 
• 403-43-0 4-fluorobenzoyl chloride 

Downstream Products

• 169052-23-7 (4-diethylphosphono)phenyl-diphenylphosine 
• 607-01-2 ethyl-diphenyl-phosphane 
• 104412-67-1 4-fluorophenyl-phosphonic acid bis(trimethylsilyl) ester 
• 349-87-1 (4-fluorophenyl)phosphonic acid 
• 1338580-35-0 ethyl (cyanomethyl)(4-fluorophenyl)phosphinate 
• 1374338-72-3 ethyl (1-cyanocyclopropyl)(4-fluorophenyl)phosphinate 
• 367493-30-9 (4-fluorophenyl)phosphonic acid monoethyl ester 
• 1443991-60-3 3,4-diphenyl-1-ethoxy-6-fluoro-benz[c-1,2]oxaphosphinine 1-oxide 
• 1443991-61-4 3-phenyl-4-methyl-1-ethoxy-6-fluoro-benz[c-1,2]oxaphosphinine 1-oxide 
• 1451210-91-5 (E)-butyl 3-(2-(diethoxyphosphoryl)-5-fluorophenyl)acrylate 
• 1605306-35-1 C₁₁H₁₃FNO₃P 
• 18437-71-3 p-fluorophenylphosphine 
• 657-81-8 4-fluorophenylphosphonic dichloride 

Relevant academic research and scientific papers

Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine

In this work, we developed a ligand- and base-free visible-light-mediated protocol for the photoredox syntheses of arylphosphonates and, for the first time, alkyl phosphonates. Zinc phthalocyanine-photocatalyzed Csp2-P and Csp3-P bond formations were efficiently achieved by reacting aryl/alkylhydrazines with trialkylphosphites in the presence of air serving as an abundant oxidant. The reaction conditions tolerated a wide variety of functional groups.

Microwave assisted P–C coupling reactions without directly added P-ligands

Our group introduced a green protocol for the Pd(OAc)2- or NiCl2-catalyzed P–C coupling reaction of aryl halides and various > P(O)H-compounds under MW conditions without directly added P-ligands. The reactivity of a few aryl derivatives in the Pd(OAc)2-catalyzed Hirao reaction was also studied. An induction period was observed in the reaction of bromobenzene and diphenylphosphine oxide. Finally, the less known copper(I)-promoted P–C coupling reactions were investigated experimentally. The mechanism was explored by quantum chemical calculations.

Photoinduced transition-metal and external photosensitizer free cross-coupling of aryl triflates with trialkyl phosphites

Photoinduced phosphonation of aryl triflates with trialkyl phosphites via a tandem single-electron-transfer, C-O bond cleavage and Arbuzov rearrangement process in the absence of transition-metal and external photosensitizer is reported herein. The protoc

Nickel-Catalyzed Phosphorylation of Tosylates

Abstract: Four new bidentate phosphine ligands have been synthesized, characterized and evaluated in Ni-catalyzed C–P coupling reaction. The readily available and inexpensive highly active sulfonate Ni(cod)2-L8 catalyzes the reaction leading to

Cobalt catalyzed C-P bond formation by cross-coupling of boronic acids with P(O)H compounds in presence of zinc

In our current work, we have reported the first cobalt-catalyzed cross-coupling of arylboronic acid with alkyl/aryl phosphites under mild conditions. The reaction was carried out in the presence of zinc powder as an additive and ter-pyridine as a ligand. The use of non-precious cobalt salt makes the protocol advantageous, as it is inexpensive and more abundant than the previously used methods where precious metal salts (Pd and Pt) were used. The reaction has a wide substrate scope and the products were obtained in good yields.

Synthesis, characterization and properties of titanium phosphonate clusters

Titanium phosphonate clusters were synthesized by the reactions of titanium tetraisopropoxide (Ti(OiPr)4) with arylphosphonic acids (ArPO3H2, Ar = Ph, 1-Nap, 4-MeOPh, 4-FPh, 4-ClPh, 4-BrPh, and 4-BrBn) and H2O in tetrahydrofuran (THF) at room temperature. [Ti4(μ3-O)(OiPr)5(μ-OiPr)3(O3PAr)3]·solv (Ar = Ph (1), 1-Nap (2), 4-MeOPh (3), 4-FPh (4), 4-ClPh (5); solv = thf for 1 and 2 or 2-propanol for 3–5) were isolated as new Ti4P3-type clusters, while Ti7(μ3-O)2(OiPr)6(μ-OiPr)6(O3PBnBr)6 (6) was isolated as a Ti7P6-type cluster. A co-crystal of Ti4P3- (7a) and Ti7P6-type (7b) clusters were obtained when 4-BrPhPO3H2 was used, and [Ti(OiPr)(acac)(O3PPh)]4 (8), a new cage cluster, was obtained when Ti(acac)2(OiPr)2 (Hacac = acetylacetone) was reacted with PhPO3H2.

Avisible-light-promoted metal-free strategy towards arylphosphonates: Organic-dye-catalyzed phosphorylation of arylhydrazines with trialkylphosphites

A visible-light-induced metal-free catalytic system was developed for the synthesis of arylphosphonates starting from arylhydrazines and trialkylphosphites. By using the inexpensive eosin B as catalyst, sub-stoichiometric amounts of DABCO, and ambient air as oxidant, diverse arylphosphonates were obtained under visible-light irradiation. Notably, this catalytic system is suitable for gram-scale reaction by utilizing sunlight as an illumination source.

Visible-Light-Mediated Metal-Free Synthesis of Aryl Phosphonates: Synthetic and Mechanistic Investigations

This work describes a straightforward access to a large variety of aryl phosphonates by the simple combination of diaryliodonium salts with phosphites in the presence of a base and under visible-light illumination. The reaction proceeds smoothly, tolerates various functionalities, and was applied for the synthesis of pharmaceutically relevant compounds. Mechanistic investigations, including EPR, NMR, and DFT calculations, support the postulated reaction mechanism.

Decarbonylative Phosphorylation of Amides by Palladium and Nickel Catalysis: The Hirao Cross-Coupling of Amide Derivatives

Considering the ubiquity of organophosphorus compounds in organic synthesis, pharmaceutical discovery agrochemical crop protection and materials chemistry, new methods for their construction hold particular significance. A conventional method for the synthesis of C?P bonds involves cross-coupling of aryl halides and dialkyl phosphites (the Hirao reaction). We report a catalytic deamidative phosphorylation of a wide range of amides using a palladium or nickel catalyst giving aryl phosphonates in good to excellent yields. The present method tolerates a wide range of functional groups. The reaction constitutes the first example of a transition-metal-catalyzed generation of C?P bonds from amides. This redox-neutral protocol can be combined with site-selective conventional cross-coupling for the regioselective synthesis of potential pharmacophores. Mechanistic studies suggest an oxidative addition/transmetallation pathway. In light of the importance of amides and phosphonates as synthetic intermediates, we envision that this Pd and Ni-catalyzed C?P bond forming method will find broad application.