5076-68-6

Usage

Uses

Used in Organic Synthesis:
Phosphoric acid, diethyl 4-methoxyphenyl ester is used as a reagent in organic synthesis for various chemical reactions, contributing to the formation of desired products.
Used in Pharmaceutical Production:
In the pharmaceutical industry, Phosphoric acid, diethyl 4-methoxyphenyl ester serves as an intermediate, playing a crucial role in the synthesis of various medications.
Used in Agrochemical Production:
Similarly, in the agrochemical sector, Phosphoric acid, diethyl 4-methoxyphenyl ester acts as an intermediate, aiding in the development of different agricultural chemicals.
Used in Manufacturing Industrial Products:
Phosphoric acid, diethyl 4-methoxyphenyl ester is used in the manufacturing of various industrial products such as plasticizers, lubricants, and flame retardants, enhancing their performance and properties.
Safety Precautions:
It is important to handle Phosphoric acid, diethyl 4-methoxyphenyl ester with caution due to its toxic nature and potential to cause irritation to the skin, eyes, and respiratory system.

Upstream product

• 20464-68-0 4-methoxyphenyl phosphorodichloridate 
• 1122-95-8 sodium 4-methoxyphenolate 
• 814-49-3 diethyl chlorophosphate 
• 150-76-5 4-methoxy-phenol 
• 762-04-9 phosphonic acid diethyl ester 
• 66107-29-7 4-methoxyphenyl triflate 
• 54058-00-3 diethyl phosphite potassium salt 
• 29368-59-0 p-methoxyphenolate 
• 113947-93-6 N-(diethoxyphosphoryl)imidazolium ion 
• 681035-21-2 (2-oxo-5,5-diphenyl-oxazolidin-3-yl)-phosphonic acid diethyl ester 
• 311-45-5 paraoxon 
• 64-17-5 ethanol 
• 27856-12-8 4-methoxyphenyl phosphate 
• 78-40-0 triethyl phosphate 

Downstream Products

• 2749-94-2 1-methoxy-4-(prop-1-yn-1-yl)benzene 
• 100-66-3 methoxybenzene 
• 131558-77-5 4-(hexyn-1-yl)anisole 
• 24962-83-2 (±)-5-(4-methoxybenzyl)dihydrofuran-2(3H)-one 
• 129529-21-1 2-(Diethyl-phosphinoyl)-4-methoxy-phenol 
• 940-00-1 (4-methoxyphenyl)trimethylstannane 
• 1097200-03-7 1-(2-ethoxy-2-methoxyethyl)-4-methoxybenzene 
• 64-18-6 formic acid 
• 598-02-7 Diethyl phosphate 
• 150-78-7 1,4-dimethoxybezene 
• 76000-82-3 Ethyl (4-methoxyphenyl) hydrogen phosphate 
• 171364-79-7 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 129529-31-3 diisopropyl 2-hydroxyphenylphosphonate 
• 80615-41-4 diethyl ether of 2-hydroxy-5-methoxyphenylphosphonic acid 

Relevant academic research and scientific papers

Selective hydrolysis of phosphorus(v) compounds to form organophosphorus monoacids

An azide and transition metal-free method for the synthesis of elusive phosphonic, phosphinic, and phosphoric monoacids has been developed. Inert pentavalent P(v)-compounds (phosphonate, phosphinate, and phosphate) are activated by triflate anhydride (Tf2O)/pyridine system to form a highly reactive phosphoryl pyridinium intermediate that undergoes nucleophilic substitution with H2O to selectively deprotect one alkoxy group and form organophosphorus monoacids.

Electrochemical phosphorylation of arenols and anilines leading to organophosphates and phosphoramidates

A practical phosphorylation for generating organophosphates and phosphoramidatesviaelectrochemical dehydrogenative cross-coupling of P(O)H compounds with arenols and anilines is disclosed. This method involves using inorganic iodide salts as both redox catalysts and electrolytes in an undivided cell without the addition of oxidants or bases. A preliminary mechanistic study suggests that radicals are not involved in this process. This method is green and eco-friendly and has good functional group tolerance, high yields and broad substrate scope, with the potential for practical synthesis.

Diselenide-Mediated Catalytic Functionalization of Hydrophosphoryl Compounds

We report a diaryldiselenide catalyst for cross-dehydrogenative nucleophilic functionalization of hydrophosphoryl compounds. The proposed organocatalytic cycle closely resembles the mechanism of the Atherton-Todd reaction, with the catalyst serving as a recyclable analogue of the halogenating agent employed in the named reaction. Phosphorus and selenium NMR studies reveal the existence of a P-Se bond intermediate, and structural analyses indicate a stereospecific reaction.

Transition State Analysis of the Reaction Catalyzed by the Phosphotriesterase from Sphingobium sp. TCM1

Organophosphorus flame retardants are stable toxic compounds used in nearly all durable plastic products and are considered major emerging pollutants. The phosphotriesterase from Sphingobium sp. TCM1 (Sb-PTE) is one of the few enzymes known to be able to hydrolyze organophosphorus flame retardants such as triphenyl phosphate and tris(2-chloroethyl) phosphate. The effectiveness of Sb-PTE for the hydrolysis of these organophosphates appears to arise from its ability to hydrolyze unactivated alkyl and phenolic esters from the central phosphorus core. How Sb-PTE is able to catalyze the hydrolysis of the unactivated substituents is not known. To interrogate the catalytic hydrolysis mechanism of Sb-PTE, the pH dependence of the reaction and the effects of changing the solvent viscosity were determined. These experiments were complemented by measurement of the primary and secondary 18-oxygen isotope effects on substrate hydrolysis and a determination of the effects of changing the pKa of the leaving group on the magnitude of the rate constants for hydrolysis. Collectively, the results indicated that a single group must be ionized for nucleophilic attack and that a separate general acid is not involved in protonation of the leaving group. The Br?nsted analysis and the heavy atom kinetic isotope effects are consistent with an early associative transition state with subsequent proton transfers not being rate limiting. A novel binding mode of the substrate to the binuclear metal center and a catalytic mechanism are proposed to explain the unusual ability of Sb-PTE to hydrolyze unactivated esters from a wide range of organophosphate substrates.

LiI/TBHP Mediated Oxidative Cross-Coupling of P(O)–H Compounds with Phenols and Various Nucleophiles: Direct Access to the Synthesis of Organophosphates

An efficient and mild method for the direct phosphorylation of phenols, alcohols, and amines with P(O)–H has been reported by LiI/TBHP mediated oxidative cross-coupling reaction. Moreover, this protocol extended to β-keto esters for the synthesis of enol phosphates using H-phosphonates. Notably, this developed method applied for the synthesis of organopesticides such as paraoxon, cyanophos, and methyl parathion. The key features of this protocol are mild conditions, short reaction time, good functional group tolerance, and broad substrate scope.

Tf2O-Promoted Activating Strategy of Phosphate Analogues: Synthesis of Mixed Phosphates and Phosphinate

A metal-, toxic chloride reagent-free activating strategy of various phosphates has been developed. This method enables the facile synthesis of functional phosphates such as alkyl phosphates, aza phosphates, thiophosphate, and mixed diaryl phosphates. A transient phosphorylpyridin-1-ium species in situ generated from phosphates with Tf2O/pyridine readily undergoes a substitution reaction with diverse nucleophiles to form versatile phosphate compounds.

Nucleophilic substitution reactions of diethyl 4-nitrophenyl phosphate triester: Kinetics and mechanism

The reactions of diethyl 4-nitrophenyl phosphate (1) with a series of nucleophiles: phenoxides, secondary alicyclic (SA) amines, and pyridines are subjected to a kinetic study. Under excess of nucleophile, all the reactions obey pseudo-first-order kinetics and are first order in the nucleophile. The nucleophilic rate constants (kN) obtained are pH independent for all the reactions studied. The Bronsted-type plot (log kN vs. pKa nucleophile) obtained for the phenolysis is linear with slope β=0.21; no break was found at pKa 7.5, consistent with a concerted mechanism. The Bronsted-type plots for the SA aminolysis and pyridinolysis are linear with slopes β=0.39 and 0.43, respectively, also suggesting concerted processes. The concerted mechanisms for the latter reactions are proposed on the basis of the lack of break in the Bronsted-type plots and the instability of the hypothetical pentacoordinate intermediates formed in these reactions.

Phosphorylation of alcohols with N-phosphoryl oxazolidinones employing copper(II) triflate catalysis

(Chemical Equation Presented) Phosphoryl transfer from N-phosphoryl 5,5-diphenyl oxazolidinone is efficiently catalyzed by copper(II) triflate. The utility of this method has been demonstrated in the phosphorylation of representative primary, secondary, tertiary, phenolic, and allylic alcohols. These reaction conditions are significantly milder than employing alkoxides and allow the phosphorylation of biologically relevant molecules.

Mechanistic studies of la3+- And Zn2+-catalyzed methanolysis of aryl phosphate and phosphorothioate triesters. Development of artificial phosphotriesterase systems

The methanolyses of a series of O,O-diethyl O-aryl phosphates (2,5) and O,O-diethyl S-aryl phosphorothioates (6) promoted by methoxide and two metal ion systems, (La3+)2(-OCH3)2 and 4:Zn2+:-OCH3 (4 = 1,5,9- triazacyclododecane) has been studied in methanol at 25°C. Bronsted plots of the log k2 values vs. sspKa for the phenol leaving groups give βlg values of -0.70. -1.43 and -1.12 for the methanolysis of the phosphates and -0.63, -0.87 and -0.74 for the methanolysis of the phosphorothioates promoted by the methoxide, La 3+ and Zn2+ systems respectively. The kinetic data for the metal-catalyzed reactions are analyzed in terms of a common mechanism where there is extensive cleavage of the P-XAr bond in the rate-limiting transition state. The relevance of these findings to the mechanism of action of the phosphotriesterase enzyme is discussed. The Royal Society of Chemistry 2005.