3862-09-7

Upstream product

• 150-76-5 4-methoxy-phenol 
• 142-45-0 Acetylenedicarboxylic acid 
• 19909-81-0 tris(p-methoxyphenyl)phosphite 

Downstream Products

• 112381-05-2 C₂₁H₂₁O₇P 
• 27347-14-4 N-(4-methoxyphenyl)morpholine 
• 55251-46-2 N-(4-methoxyphenyl)-N-methylaniline 

Relevant academic research and scientific papers

Diphenyl Diselenide-Catalyzed Synthesis of Triaryl Phosphites and Triaryl Phosphates from White Phosphorus

Industrially important triaryl phosphites, traditionally prepared from PCl3, have been synthesized by a diphenyl diselenide-catalyzed one-step procedure involving white phosphorus and phenols, which provides a halogen- and transition metal-free way to these compounds. Subsequent oxidation of triaryl phosphites produces triaryl phosphates and triaryl thiophosphates. Phosphorotrithioates are also prepared efficiently from aromatic thiols and aliphatic thiols.

Aerobic Oxidation of Phosphite Esters to Phosphate Esters by Using an Ionic-Liquid-Supported Organotelluride Reusable Catalyst

We describe the synthesis of an ionic-liquid (IL)-supported organotelluride catalyst and its application as a recyclable catalyst for the aerobic oxidation of phosphite esters to phosphate esters. This method shows high conversion rates, allows the ready isolation and purification of the resulting products, and exhibits good reusability of the catalyst.

Nickel-catalyzed amination of aryl phosphates through cleaving aryl C-O bonds

The amination of triaryl phosphates was achieved using a Ni(II)-(σ-Aryl) complex/NHC catalyst system in dioxane at 110 °C in the presence of NaH as base. Electron-neutral, -rich, and -deficient triaryl phosphates were coupled with a wider range of amine partners including cyclic and acyclic secondary amines, aliphatic primary amines, and anilines in good to excellent yields.

Aerobic photooxidation of phosphite esters using diorganotelluride catalysts

Diorganotellurides containing bulky aromatic substituents are found to catalyze the photooxidation of phosphite esters using aerobic oxygen as a terminal oxidant. A Hammett plot with substituted triaryl phosphites yielding p = 2.88 agrees with a nucleophilic oxygen transfer from telluroxide to phosphite.2009 American Chemical Society.

Evaluation of kinetic parameters from the synthesis of triaryl phosphates using reaction calorimetry

Triaryl phosphates were prepared by a "one-pot" methodology through the reaction of sodium phenoxides with phosphorus oxychloride. This system can be described as a semi-batch reaction, where the phenoxides were synthesized inside the reactor anda solution of phosphorus oxychloride in toluene was added continuously through a pump. These highly exothermic reactions were performed in a Mettler RC-1 reaction calorimeter. The aim of this work was to evaluate the reaction rate and the reaction rate constant through the study of the rate of heat release. Although the phenoxides react almost immediately with phosphorus oxychloride, it was possible to notice the slight differences among the sodium phenoxides studied. The phenoxide bearing an electron-donating group (methoxy) was the most reactive, and the one bearing an electron-withdrawing group (nitro) was the least reactive one. The reactions could be considered to be feed-controlled. It was demonstrated that the reaction temperature does not affect the reaction rate and reaction rate constant in the same way that the feed rate of the phosphorus oxychloride does.

Preparation and photolysis of diaryl esters of acetylenedicarboxylic acid

Two diaryl acetylenedicarboxylates 1 a,b have been prepared in moderate yields by direct reaction of acetylenedicarboxylic acid with the corresponding phenols catalyzed by sulfuric or p-toluenesulfonic acids and also through acetylenedicarbonyl chloride. The accompanying by-products have been characterized. Attempted esterification using N,N'-dicyclohexylcarbodiimide as condensing agent gives an asymmetric ester amide 11a and a substituted uracil 12a. Photolysis of the aryl ester 1 a,b in benzene solution affords the benzocoumaran-3-ones 14 a,b. In the case of 1b, minor amounts of a polycyclic condensed 4-chromanone 17b have also been observed. These results show that the nature of the substituent attached at the β-position of the C ≡ C triple bond plays an important role in the cyclization of o-hydroxyaryl ethynyl ketones.

Metalation-Induced Double Migration of Phosphorus from O-->C. Convenient Preparation of Bis(2-hydroxyaryl)phosphinic Acids

Treatment of diaryl ethyl phosphates 8 with lithium diisopropylamide in tetrahydrofuran yields ethyl bis(2-hydroxyaryl)phosphinates 9.The reaction involves the double migration of phophorus from O-->C and is probably intramolecular.These phosphinate esters 9 on treatment with trimethylsilyl chloride and sodium iodide in acetonitrile undergo transesterification to give trimethylsilyl esters that yield the corresponding phosphinic acids 15 on treatment with water.