15286-13-2

Usage

Uses

Used in Flame Retardant Industry:
M-TOLYL-PHOSPHONIC ACID DIETHYL ESTER is used as a flame retardant for its ability to inhibit the combustion of materials, making it an effective additive in manufacturing fire-resistant products.
Used in Plasticizer Industry:
M-TOLYL-PHOSPHONIC ACID DIETHYL ESTER is used as a plasticizer to increase the flexibility and workability of various materials.
Used in Pharmaceutical Synthesis:
M-TOLYL-PHOSPHONIC ACID DIETHYL ESTER is used as an intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Synthesis:
M-TOLYL-PHOSPHONIC ACID DIETHYL ESTER is used as an intermediate in the synthesis of agrochemicals, aiding in the production of effective pesticides and other agricultural products.
Used in Organic Compound Synthesis:
M-TOLYL-PHOSPHONIC ACID DIETHYL ESTER is used as an intermediate in the synthesis of various organic compounds, facilitating the creation of new chemical entities with potential applications in different industries.

InChI:InChI=1/C11H17O3P/c1-4-13-15(12,14-5-2)11-8-6-7-10(3)9-11/h6-9H,4-5H2,1-3H3

Upstream product

• 625-95-6 3-Iodotoluene 
• 122-52-1 triethyl phosphite 
• 52057-48-4 diethyl trimethylsilyl phosphate 
• 591-17-3 meta-bromotoluene 
• 762-04-9 phosphonic acid diethyl ester 
• 2303-76-6 sodium diethyl phosphite 
• 108-88-3 toluene 
• 2942-58-7 diethyl cyanophosphonate 
• 28987-79-3 m-tolylmagnesium bromide 
• 17933-03-8 m-tolylboronic acid 
• 3955-72-4 3-methylphenyl tosylate 
• 108-39-4 3-methyl-phenol 
• 15898-38-1 sodium 3-methylbenzenesulfinate 
• 18412-56-1 3-methylphenyltriethoxysilane 

Downstream Products

• 77918-48-0 m-tolylphosphonic acid 
• 1443991-77-2 3,4-bis(4-methoxyphenyl)-1-ethoxy-7-methylbenz[c-1,2]oxaphosphinine 1-oxide 
• 1443991-79-4 3-phenyl-4-methyl-1-ethoxy-7-methylbenz[c-1,2]oxaphosphinine 1-oxide 
• 63818-67-7 3-methylphenyl phosphonic acid monoethyl ester 
• 1451210-90-4 (E)-butyl 3-(2-(diethoxyphosphoryl)-4-methylphenyl)acrylate 
• 1451211-02-1 (E)-diethyl (2-(1,2-diphenylvinyl)-5-methylphenyl)phosphonate 
• 1451211-03-2 (Z)-diethyl (2-(1,2-diphenylvinyl)-5-methylphenyl)phosphonate 
• 1464720-95-3 (E)-ethyl 3-(2-(diethoxyphosphoryl)-4-methylphenyl)acrylate 
• 1605306-41-9 C₁₂H₁₆NO₃P 

Relevant academic research and scientific papers

Synthesis of aryl phosphonates by reaction of Grignard reagents with diethyl cyanophosphonate

Reaction of Grignard reagents with diethyl cyanophosponate gave aryl phosphonates under mild conditions and in good yield.

The Synthesis of Biarylmonophosphonates via Palladium-Catalyzed Phosphonation, Iridium-Catalyzed C-H Borylation, Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling

Abstract: The iridium-catalyzed C-H borylation of diethyl phenylphosphonate results in nonselective mono and bisborylation to afford a near statistical mixture of 3-, 3,5- and 4-boryl substituted aryl phosphonates whereas 3-substituted aryl phosphonates u

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.

Nickel-Catalyzed Electrochemical Phosphorylation of Aryl Bromides

A nickel-catalyzed electrochemical cross-coupling reaction of aryl bromides with dialkyl phosphites, ethyl phenylphosphinate, and diphenylphosphine oxide has been developed. This reaction utilizes a simple undivided cell with inexpensive carbon electrodes to synthesize aryl phosphonates, aryl phosphinates, and arylphosphine oxides at room temperature. This protocol provides a mild and efficient route for the construction of C-P bond in moderate to high yields with broad substrate scope.

Catalyst-free phosphorylation of aryl halides with trialkyl phosphites through electrochemical reduction

A catalyst-free electrochemical cross-coupling reaction of aryl halides with trialkyl phosphite has been developed. This reaction proceeds in an undivided cell with a low-cost Ni anode and a graphite cathode under mild and neutral conditions. A wide range of functional groups are well-tolerated and the phosphorylated product can be obtained on the gram scale, showing that this transformation has the potential to be a valuable method for the construction of aromatic carbon-phosphorus bonds.

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.

A palladium-catalyzed oxidative cross-coupling reaction between aryl pinacol boronates and H-phosphonates in ethanol

The first successful oxidative coupling reaction of aryl pinacol boronic esters with H-phosphonates to deliver aryl phosphorous compounds is reported herein. These reactions between aryl boronic reagents and H-phosphonates were carried out synergistically using a Pd catalyst, additive and oxidant. Without using bases and ligands, phosphorylation was accomplished in an environmentally-friendly manner under mild conditions in ethanol.

Ar-P bond construction by the Pd-catalyzed oxidative cross-coupling of arylsilanes with H-phosphonates via C-Si bond cleavage

A novel and efficient methodology that allows for the construction of Ar-P bonds via the Pd-catalyzed oxidative cross-coupling reaction of various arylsilanes with H-phosphonates leading to valuable arylphosphonates has been developed.