28036-18-2

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
Diethyl (2-chlorophenyl)phosphonate serves as an essential intermediate in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides.
Used as a Pesticide and Insecticide:
Due to its properties, diethyl (2-chlorophenyl)phosphonate is used as a pesticide and insecticide, helping to control and eliminate pests in agricultural and other settings.
Used as a Flame Retardant:
Diethyl (2-chlorophenyl)phosphonate is utilized as a flame retardant, enhancing the fire safety of various materials and products.
Used in the Production of Plasticizers:
diethyl (2-chlorophenyl)phosphonate is also employed in the production of plasticizers, which are additives that increase the flexibility and workability of plastics.
Used in Chemical Warfare (with caution):
Although not a primary use, diethyl (2-chlorophenyl)phosphonate is a potential precursor for the synthesis of nerve agents. Its potential role in chemical warfare has led to scrutiny and concerns regarding its application in this context.

Upstream product

• 762-04-9 Diethyl phosphonate 
• 66107-36-6 2-chlorophenyl triflate 
• 108-90-7 chlorobenzene 
• 762-04-9 phosphonic acid diethyl ester 
• 1956-97-4 2-chlorobenzenediazonium tetrafluoroborate 
• 122-52-1 triethyl phosphite 
• 615-41-8 2-iodochlorobenzene 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 3900-89-8 2-Chlorobenzeneboronic acid 

Downstream Products

• 881923-55-3 (2-chlorophenyl)phosphonic acid monoethyl ester 
• 1464720-91-9 (E)-ethyl 3-(3-chloro-2-(diethoxyphosphoryl)phenyl)acrylate 

Relevant academic research and scientific papers

Direct synthesis of ortho-halogenated arylphosphonates via a three-component reaction involving arynes

A three-component reaction involving arynes, trialkyl phosphites, and halides has been achieved under mild reaction conditions. This transformation provides a direct synthetic approach to ortho-halogenated arylphosphonates, which could be rapidly converted to diversely ortho-functionalized arylphosphorus com ounds

Arylphosphonate-Directed Ortho C-H Borylation: Rapid Entry into Highly-Substituted Phosphoarenes

Phosphonate-directed ortho C-H borylation of aromatic phosphonates is reported. Using simple starting materials and commercially accessible catalysts, this method provides steady access to o-phosphonate arylboronic esters bearing pendant functionality and flexible substitution patterns. These products serve as flexible precursors for a variety of highly substituted phosphoarenes, and in situ downstream functionalization of the products is described.

Direct conversion of phosphonates to phosphine oxides: An improved synthetic route to phosphines including the first synthesis of methyl JohnPhos

The synthesis of tertiary phosphine oxides from phosphonates was achieved reliably and in good to excellent yields using stoichiometric amounts of alkyl or aryl Grignard reagents and sodium trifluoromethanesulfonate (NaOTf). In the absence of the NaOTf additive, covalent coordination oligomers of magnesium and phosphorus species dominate the reaction, producing very low yields of phosphine oxide, but high conversions of the phosphonate starting material. Mechanistic studies revealed that a five-coordinate phosphorus species - not a phosphinate - is the reaction intermediate. A diverse array of phosphonates was converted to phosphine oxides using a variety of Grignard reagents for direct carbon-phosphorus functionalization. This new methodology especially simplifies the synthesis of dimethylphosphino (RPMe2)-type phosphines by using air-, water-, and silica-stable intermediates. To highlight this reaction, a new Buchwald-type ligand ([1,1′-biphenyl]-2-yldimethylphosphine, or methyl JohnPhos) and a classic bidentate phosphine, bis(diphenylphosphino)propane (dppp), were synthesized in excellent yields.

Arenediazonium tetrafluoroborates in palladium-catalyzed C-P bond-forming reactions. Synthesis of arylphosphonates, -phosphine oxides, and -phosphines

A novel palladium-catalyzed synthesis of arylphosphonates from arenediazonium tetrafluoroborates and triethylphosphite or diethylphosphite is presented. The reaction tolerates useful substituents including bromo, chloro, nitro, ether, cyano, keto, and ester groups, can be performed as a one-pot process from anilines omitting the isolation of arenediazonium salts, and can be extended to the preparation of arylphosphine oxides and arylphosphines.

Oxidative Phoshonylation of Aromatics with Ammonium Cerium(IV) Nitrate

Arylphosphonates 5 and 6 can be prepared in good yields in a one-step synthesis starting from arenes with tri- or diethylphosphites and cerium ammonium nitrate (CAN) as oxidant.The seletivity of the oxidative phosphonylation is relatively low; the reactive species is a phosphite radical cation.

Palladium-Catalyzed Reaction of Aryl Polyfluoroalkanesulfonates with O,O-Dialkyl Phosphonates

Arylphosphonates were synthesized by the reaction of aryl polyfluoroalkanesulfonates with O,O-dialkyl phpsphonates in the presence of triethylamine under palladium catalysis in good to excellent yield.

OXIDATIVE PHOSPHONYLATION OF AROMATIC COMPOUNDS

Aryl phosphonates can be prepared in good yield from the respective arenes and tri- or dialkylphosphites by either chemical or anodic oxidation.The anodic oxidation proceeds either via phosphinium radical cations, which then attack the arenes electrophilically, or via arene radical cations, which add the trialkylphosphite as nucleophile.Aryl phosphonates are also obtained in good yield by chemical oxidation with peroxodisulfate/AgNO3 in acetonitrile/water or glacial acetic acid.The diethylphosphinium radical cation, formed from diethylphosphite by oxidation with Ag(II), is supposed to be the reactive species in this process.Raising the silver salt concentration leads to an increase in polyphosphonylation.Selectivity ratios were determined for the oxidative phosphonylation process.