77918-46-8

Usage

Uses

Used in Pesticide and Herbicide Applications:
(4-Trifluoromethyl-phenyl)-phosphonic acid diethyl ester is utilized as a pesticide and herbicide in agricultural and pest control industries. Its effectiveness stems from its ability to act as a reversible inhibitor of acetylcholinesterase, leading to a disruption in the nervous system of insects and pests. This results in their eventual death, making the compound a valuable tool for controlling and eliminating unwanted pests in various settings.
Used in Agricultural Industry:
In the agricultural sector, (4-Trifluoromethyl-phenyl)-phosphonic acid diethyl ester is employed as a means to protect crops from damaging insects and pests. Its application helps ensure healthy crop growth and contributes to increased yields, which is vital for sustaining food production and meeting the demands of a growing population.

InChI:InChI=1/C11H14F3O3P/c1-3-16-18(15,17-4-2)10-7-5-9(6-8-10)11(12,13)14/h5-8H,3-4H2,1-2H3

Upstream product

• 402-43-7 p-trifluoromethylphenyl bromide 
• 814-49-3 diethyl chlorophosphate 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 762-04-9 phosphonic acid diethyl ester 
• 455-13-0 4-Iodobenzotrifluoride 
• 122-52-1 triethyl phosphite 
• 871362-15-1 bis(4-(trifluoromethyl)phenyl)iodonium trifluoromethanesulfonate 
• 368-90-1 4-(trifluoromethyl)phenylhydrazine 
• 455-14-1 4-trifluoromethylphenylamine 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 98-56-6 4-chlorobenzotrifluoride 
• 136918-14-4 phthalimide 
• 402-51-7 4-(trifluoromethyl)phenylmagnesium bromide 
• 214360-65-3 4-trifluoromethylphenylboronic acid pinacol ester 

Downstream Products

• 607353-85-5 ((4-trifluoromethyl)benzene)phosphono chloridic acid ethyl ester 
• 1869-27-8 [4-(trifluoromethyl)phenyl]phosphonic acid 
• 473808-83-2 (4-(trifluoromethyl)phenyl)phosphine 

Relevant academic research and scientific papers

Reversing the Tradeoff between Rate and Overpotential in Molecular Electrocatalysts for H2 Production

A longstanding challenge in molecular electrocatalysis is to design catalysts that break away from the tradeoff between rate and overpotential arising from electronic scaling relationships. Here we report an inversion of the rate-overpotential correlation

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.

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.

Phosphine Oxides from a Medicinal Chemist's Perspective: Physicochemical and in Vitro Parameters Relevant for Drug Discovery

Phosphine oxides and related phosphorus-containing functional groups such as phosphonates and phosphinates are established structural motifs that are still underrepresented in today's drug discovery projects, and only few examples can be found among approved drugs. In this account, the physicochemical and in vitro properties of phosphine oxides and related phosphorus-containing functional groups are reported and compared to more commonly used structural motifs in drug discovery. Furthermore, the impact on the physicochemical properties of a real drug scaffold is exemplified by a series of phosphorus-containing analogs of imatinib. We demonstrate that phosphine oxides are highly polar functional groups leading to high solubility and metabolic stability but occasionally at the cost of reduced permeability. We conclude that phosphine oxides and related phosphorus-containing functional groups are valuable polar structural elements and that they deserve to be considered as a routine part of every medicinal chemist's toolbox.

Arylphosphate compound and preparation method thereof

The invention discloses an arylphosphate compound and a preparation method thereof. The preparation method includes, with arylamine and phosphite ester as reactants and tert-butyl nitrite as an accelerator, performing stirring reaction at the temperature within 70-80 DEG C for 40-60 minutes, and separating through the column chromatography to obtain a product, namely arylphosphate compound. The preparation method is a new way of synthetizing arylphosphate target compound from low-price feasible raw materials of arylamine and phosphite ester on the acid-free and metal-free condition, has the advantages of mild reaction condition, operational simplicity and the like and overcomes the big trouble to production of medical intermediates caused by residues of metal catalysts, after-treatment ofacids in medicine synthesis, and accordingly, the simple and efficient meta-free and acid-free catalysis system has great potential application value and economic benefit.

Decarbonylative Phosphorylation of Carboxylic Acids via Redox-Neutral Palladium Catalysis

We describe the direct synthesis of organophosphorus compounds from ubiquitous aryl and vinyl carboxylic acids via decarbonylative palladium catalysis. The catalytic system shows excellent scope and tolerates a wide range of functional groups (>50 examples). The utility of this powerful methodology is highlighted in the late-stage derivatization directly exploiting the presence of the prevalent carboxylic acid functional group. DFT studies provided insight into the origin of high bond activation selectivity and P(O)-H isomerization pathway.

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.

Photoinduced Transition-Metal-Free Cross-Coupling of Aryl Halides with H-Phosphonates

Photoinduced transition-metal- and photosensitizer-free cross-coupling of aryl halides (including Ar-Cl, Ar-Br, and Ar-I) with H-phosphonates (including dialkyl phosphonates and diarylphosphine oxides) is reported. Various functional groups were tolerated, including ester, methoxy, dimethoxy, alkyl, phenyl, trifluoromethyl, and heterocyclic compounds. This simple and green strategy provides a practical pathway to synthesize arylphosphine oxides.

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.