78-32-0Relevant academic research and scientific papers
Diphenyl Diselenide-Catalyzed Synthesis of Triaryl Phosphites and Triaryl Phosphates from White Phosphorus
Zhang, Yue,Cai, Ziman,Chi, Yangyang,Zeng, Xiangzhe,Chen, Shuanghui,Liu, Yan,Tang, Guo,Zhao, Yufen
, p. 5158 - 5163 (2021/07/20)
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
Mihoya, Aya,Shibuya, Yuga,Ito, Akane,Toyoda, Anna,Oba, Makoto,Koguchi, Shinichi
supporting information, p. 2043 - 2045 (2020/11/10)
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
Huang, Jin-Hua,Yang, Lian-Ming
supporting information; experimental part, p. 3750 - 3753 (2011/09/14)
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.
Reaction kinetics on hydrolysis of substituted di-phenyl phosphate ester in different borate buffers
Kumar, Adesh,Yadav
body text, p. 863 - 867 (2011/04/25)
The reaction of hydroxide ion with di-4-methyl phenyl phosphate has been studied in the presence of micelles of cationic detergent. It has been investigated at pH 8.0 to 10.0 at 40 ± 0.10°C in aqueous dioxane di-phosphate esters. Pseudo-first order rate constants kψ and k′w have been measured spectrophotometrically by rate of appearance of inorganic phosphate during hydrolysis. kψ and k′w were rate constants with and without CTAB, which varied in between 0.02 × 10-3 to 2 × 10-3 mol dm -3 and the concentration of phosphate was restricted to 5.0 × 10-3 s-1. Rate constants increase with concentrations of CTAB, giving at rate maximum, kψ = 67.03 × 10-5 s-1 at 18 × 10-3 mol dm-3 CTAB and k ψ = 52.43 × 10-5 s-1 at 16 × 10-3 mol dm-3 CTAB respectively at pH 8.0 and 9.0 for di-anions of 4-mpp. The values of ion exchange parameter calculated at pH 8.0 and 9.0 by using various ion exchange equations have been summarized. The activation energy is 25.08 kcal/mol and entropy is 52.07 [-ΔS(eu)], which bas been found at pH 8.0 and used borate buffer 3.9 × 10-3 mol dm-3 [OH-].
Aerobic photooxidation of phosphite esters using diorganotelluride catalysts
Oba, Makoto,Okada, Yasunori,Nishiyama, Kozaburo,Ando, Wataru
supporting information; experimental part, p. 1879 - 1881 (2009/10/10)
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.
Effects of triaryl phosphates on mouse and human nuclear receptors
Honkakoski, Paavo,Palvimo, Jorma J.,Penttilae, Leena,Vepsaelaeinen, Jouko,Auriola, Seppo
, p. 97 - 106 (2007/10/03)
The constitutively active receptor (CAR) is a crucial regulator of genes encoding for enzymes active in drug/steroid oxidation, conjugation, and transport. In our attempt to isolate the endogenous inhibitory ligand(s) for the mouse CAR, we found surprisingly that the inhibitory activity was associated with di- and tri-isopropylated phenyl phosphates that were present in livers of untreated mice. Trans-activation experiments in mammalian cells with synthetic compounds verified that mouse CAR was inhibited by various isopropylated phenyl phosphates (40-80%). Such triaryl phosphates are widely used as fire retardants, lubricants, and plasticizers, and some of them are known to disturb reproduction by currently unknown mechanisms. Equipped with the finding that these compounds could interact with mouse CAR, we proceeded to determine their functional effects on other nuclear receptors. Human CAR and pregnane X receptor (PXR) were variably activated (2-5-fold) by triaryl phosphates while mouse PXR, peroxisome proliferator-activated receptor-α, and vitamin D receptor were refractory. Among steroid hormone receptors, the human androgen receptor was inhibited by triphenyl phosphate and di-ortho-isopropylated phenyl phosphate (40-50%) and activated by di- and tri-para-substituted phenyl phosphates (2-fold). Our results add to the list of CAR and PXR activators and suggest steroid-dependent biological pathways that may contribute to the reproductive effects of triaryl phosphates.
Absolute viscosity and density of trisubstituted phosphoric esters
Kannan,Kishore
, p. 649 - 655 (2007/10/03)
This paper presents measurements on the absolute viscosity (η) and density (ρ) of trisubstituted phosphoric esters which are useful in understanding their flow mechanism necessary for accessing their role as plasticizers. The effect of chain length and branching has been examined on the η and ρ trends. From η data, by using the Vogel-Tammann-Fulchur (VTF) equation, the VTF temperature (To) has been obtained which also represents the ideal glass transition temperature. To is related to the flexibility of the molecules. It is observed that To initially decreases with molecular weight, reaches a minimum, and increases thereafter. The initial decrease in To has been attributed to the enhanced flexibility of the phosphate esters. Reversal of flexibility with relative molar mass beyond 400 is due to the gentle collision of the arms of the trisubstituted phosphoric esters. This has been further corroborated from the molar mass exponent as exhibited in the η-molar mass plot. The isomeric effect on η has also been investigated in tricresyl phosphates, hitherto for the first time. The ortho isomer has highest η among the isomers. The para isomer was found to have lowest To and hence highest flexibility compared to the ortho and meta isomers.
"One-pot" Synthesis of Triaryl Phosphates a Reaction Calorimetry Approach
Silva, J. F. Cajaiba da,Nakayama, H. T.,Neto, C. Costa
, p. 71 - 82 (2007/10/03)
Triaryl phosphates were obtained in yields ranging from 85-96percent in a "one-pot" synthesis via an alkaline route: an ethanolic solution of sodium hydroxide was added to a solution of substituted phenol in toluene.The mixture was distilled until all ethanol was removed.Phosphorus oxychloride was then added and the toluene was distilled.The triaryl phosphates were characterized by NMR (1H and 31P), MS and FTIR.The heat capacity (Cp), the total heat transfer coefficient (U) and the reaction enthalpy (ΔH) were determined for the synthesis of tris(4-chloro-3-methylphenyl), tris(p-cresyl), tris(o-methoxyphenyl) and tris(p-nitrophenyl) phosphates. - Keywords: Phosphate; NMR spectra; heat capacity; phosphorus oxychloride
Polymer supported reagents: An efficiant and simple method for the synthesis of triaryl phosphates
Sagar,Thorat,Salunkhe
, p. 2029 - 2033 (2007/10/02)
The reaction of phosphoryl chloride with insoluble polymer-supported phenoxide ion reagents in benzene at room temperature, produced triaryl phosphates in excellent yields. The isolation of pure products by simple filtration and evaporation is an important feature of this method.
