838-85-7

Usage

Uses

Used in Chemical Industry:
Diphenyl phosphate is used as an organic catalyst for the ring-opening polymerization (ROP) of renewable 5-alkyl δ-lactones. It facilitates the polymerization process, enabling the production of biodegradable polymers from renewable resources.
Used in Polymer Synthesis:
In combination with zinc iodide, Diphenyl phosphate forms a novel initiating system for the living cationic polymerization of isobutyl vinyl ether. This allows for the controlled synthesis of polymers with specific molecular weights and architectures, which can be tailored for various applications.
Used in Flame Retardant Industry:
As a metabolite of the flame retardant Triphenyl Phosphate (T808990), Diphenyl phosphate plays a role in the flame retardancy of various materials, contributing to fire safety in different industries.

Purification Methods

Crystallise it from CHCl3/pet ether. [Cherbuliez in Organo Phosphorus Compounds (Kosolapoff & Maier eds) Wiley Vol 6 pp 211-577 1973, Beilstein 6 IV 714.]

InChI:InChI=1/C12H11O4P/c13-17(14,15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H,(H,13,14)/p-1

Upstream product

• 115-89-9 phosphoric acid methyl ester diphenyl ester 
• 27460-01-1 n-propyl diphenyl phosphate 
• 115-86-6 phosphoric acid triphenyl ester 
• 4281-67-8 cyclohexyl diphenyl phosphate 
• 65314-76-3 phosphoric acid-(2-amino-ethyl ester)-diphenyl ester 
• 298-14-6 potassium hydrogencarbonate 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 1623-08-1 phosphoric acid dibenzyl ester 
• 4218-62-6 benzyl diphenyl phosphate 
• 108-95-2 phenol 
• 4697-37-4 ethyl metaphosphate 
• 75-91-2 tert.-butylhydroperoxide 
• 155791-59-6 Phosphoric acid 3-oxo-3H-1λ³-benzo[d][1,2]iodoxol-1-yl ester diphenyl ester 
• 930-51-8 cyclopentylacetylene 

Downstream Products

• 115-89-9 phosphoric acid methyl ester diphenyl ester 
• 10448-49-4 tetraphenyl pyrophosphate 
• 66910-81-4 phosphoric acid diphenyl ester-(2-stearoyloxy-ethyl ester) 
• 115-88-8 n-octyl diphenyl phosphate 
• 101100-85-0 (E)-3-Furan-2-yl-acrylic acid octyl ester 
• 10581-14-3 mono-octyl phenyl phosphoric acid 
• 140138-20-1 diphenyl 3-(2-furyl) acrylyl phosphate 
• 141607-22-9 diphenyl (tetra-O-acetyl-α-D-glucopyranosyl) phosphate 
• 47002-33-5 bis(4-bromophenyl)phosphoric acid 
• 645-15-8 Bis(p-nitrophenyl) phosphate 
• 108-95-2 phenol 
• 841-46-3 ethyl diphenyl phosphate 
• 60763-39-5 isopropyl diphenyl phosphate 
• 316365-07-8 diphenyl 3-O-tert-butyldimethylsilyl-4,6-di-O-(tert-butyl)silanediyl-2-O-pivaloyl-α-D-mannopyranoside phosphate 

Relevant academic research and scientific papers

Catalytic hydrolysis of phosphate esters in microemulsions

We have continued our kinetics investigation of the iodosobenzoate (IBA) catalysis of the hydrolysis of p-nitrophenyl diphenyl phosphate (PNDP), in microemulsion media composed of hexadecane in water stabilized by cetyltrimethylammonium bromide and 1-butanol over a range of water mass fractions. We have examined two iodosobenzoic acid derivatives (5-nitro-2-iodosobenzoic acid and 5-octyloxy-2-iodosobenzoic acid) as catalysts. In addition, we have determined by31P FT-NMR techniques that the major product of the hydrolysis of PNDP, both in IBA catalyzed and in uncatalyzed media, is diphenylphosphate.

Synthesis of diaryl phosphates using orthophosphoric acid as a phosphorus source

This paper presents a new synthetic route for diaryl phosphate esters, which are traditionally synthesized from phosphorus oxychloride. Specifically, we report the synthesis of diaryl phosphates by the dehydrative condensation of orthophosphoric acid, a phosphorus source, with aromatic alcohols.

Mesoporous cerium oxide for fast degradation of aryl organophosphate flame retardant triphenyl phosphate

Cerium oxide nanoparticles were prepared by calcination of basic cerous carbonate (as a precursor) obtained by precipitation from an aqueous solution. Prepared samples were characterized by X-ray diffraction (XRD), infrared spectroscopy (FTIR), high resolution scanning electron microscopy (HRSEM), BET (Brunauer-Emmett-Teller) surface area and porosity measurement. Prepared cerium oxide was applied as a destructive sorbent for the fast and safe degradation of organophosphorus flame retardant triphenyl phosphate (TPP). It was shown that cerium dioxide was effective in the decomposition of TPP by cleavage of the P-O-aryl bond in the flame retardant molecule. A degradation mechanism for TPP on the ceria surface was proposed. The degradation is governed by conversion of TPP via diphenyl phosphate (DPP) to the final product identified as phenol (Ph). The key parameter increasing the degradation efficiency of CeO2 is the temperature of calcination. At optimum calcination temperature (500 °C), the produced ceria retains a sufficiently high surface area and attains an optimum degree of crystallinity (related to a number of crystal defects, and thus potential reactive sites). The fast and efficient degradation of organophosphorus flame retardant TPP was observed in a polar aprotic solvent (acetonitrile) that is miscible with water.

O -Phthalaldehyde catalyzed hydrolysis of organophosphinic amides and other P(O)-NH containing compounds

Over 50 years ago, Jencks and Gilchrist showed that formaldehyde catalyses the hydrolysis of phosphoramidate through electrophilic activation, induced by covalent attachment to its nitrogen atom. Given our interest in the use of aldehydes as catalysts, this work was revisited to identify a superior catalyst, o-phthalaldehyde, which facilitates hydrolyses of various organophosphorus compounds bearing P(O)-NH subunits under mild conditions. Interestingly, chemoselective hydrolysis of the P(O)-N bonds could be accomplished in the presence of P(O)-OR bonds.

Neodymium tris-diarylphosphates: Systematic study of the structure-reactivity relationship in butadiene and isoprene polymerisation

The catalytic properties of neodymium tris-phosphates with various diarylphosphate ligands in the stereoregular 1,4-cis-polymerisation of butadiene and isoprene were studied. The considerable variability of the diaryl phosphate structure allowed for the systematic investigation of the dependence of the catalytic properties of neodymium tris-diarylphosphates on the electronic and steric properties of the ligand. Electron-withdrawing substituents (F, Cl, Br) in the aryl moiety increased the catalyst activity of tris-diarylphosphate. Neodymium aryl phosphates containing lipophilic bulky ligands provided the synthesis of polydienes with a monomodal molecular-weight distribution. The optimal catalytic properties demonstrated that the neodymium aryl phosphate prepared from bis(2,6-dimethyl-4-tert-butylphenyl)-phosphoric acid showed high activity and ensured a monomodal MWD of polydienes (Mw/Mn ～ 2 for polybutadiene and Mw/Mn ～ 3 for polyisoprene) in various conditions.

Synthesis, characterization and phosphotriesterase mimetic activity of some Zn(II) and Cu(II) complexes

We report here the synthesis and characterization of a few phenolate-based ligands bearing tert- amino substituent and their Zn(II) and Cu(II) metal complexes. Three mono/binuclear Zn(II) and Cu(II) complexes [Zn(L1)(H 2O)].CH3OH.Hs

NANOPARTICLE COMPOSITION AND ASSOCIATED METHODS THEREOF

A nanoparticle composition is provided, wherein the composition comprises a nanoparticulate metal oxide; and a phosphorylated polyol comprising at least two phosphate groups. The polyol comprises one or more hydrophilic groups selected from the group consisting of polyethylene ether moieties, polypropylene ether moieties, polybutylene ether moieties, and combinations of two or more of the foregoing hydrophilic moieties. A method of making the nanoparticle composition is also provided. The nanoparticle compositions provided by the present invention may be used as contrast agents in medical imaging techniques such as X-ray and magnetic resonance imaging.

DIAGNOSTIC AGENT COMPOSITION AND ASSOCIATED METHODS THEREOF

A diagnostic agent composition is provided which comprises a nanoparticle composition and a pharmaceutically acceptable carrier or excipient. The nanoparticle composition comprises a nanoparticulate metal oxide and a phosphorylated polyol, wherein the phosphorylated polyol comprises at least two phosphate groups and one or more hydrophilic groups selected from the group consisting of polyethylene ether moieties, polypropylene ether moieties, polybutylene ether moieties, and combinations of two or more of the foregoing hydrophilic moieties. The disclosure provides detailed guidance on methods of making and using such diagnostic agent compositions. The diagnostic agent compositions provided by the present invention are useful as contrast agents for medical diagnostic imaging techniques such as magnetic resonance (MR) imaging and X-ray imaging. The diagnostic agent composition may be administered to a subject via a variety of techniques, among them injection, inhalation, and ingestion.

Novel photolabile protecting group for phosphate compounds

A novel photolabile protecting group, thiochromone S,S-dioxide, containing the diazomethyl group for protection of phosphate derivatives is described. Deprotection of the successfully protected phosphate derivatives proceeded smoothly under photoirradiation using an ultrahigh-pressure mercury lamp to recover the corresponding phosphates quantitatively, and the photoproduct derived from the thiochromone derivative showed high fluorescence intensity. Georg Thieme Verlag Stuttgart · New York.

PHOTODISSOCIABLE PROTECTIVE GROUP

The present invention provides a photolabile protecting group that can be removed by light irradiation under mild conditions. More specifically, the present invention provides a method comprising protecting a reactive functional group (e.g., a hydroxyl group, amino group, carboxyl group, carbonyl group, phosphodiester group, etc.) by the photolabile protecting group, and then removing the photolabile protecting group simply by light irradiation under neutral conditions. The present invention relates to a compound represented by Formula (3): wherein Ar1 is an optionally substituted aromatic or heteroaromatic ring, Ar2 is an optionally substituted aryl or heteroaryl group, X is a leaving group, and n is an integer of 1 or 2; and a method of protecting and deprotecting an amino group etc. using the compound.