Triphenyl phosphate

Base Information

• Chemical Name: Triphenyl phosphate
• CAS No.: 115-86-6
• Deprecated CAS: 402955-02-6
• Molecular Formula: C18H15O4P
• Molecular Weight: 326.288
• Hs Code.: HOSPHATE PRODUCT IDENTIFICATION
• European Community (EC) Number: 204-112-2
• ICSC Number: 1062
• NSC Number: 57868
• UNII: YZE19Z66EA
• DSSTox Substance ID: DTXSID1021952
• Nikkaji Number: J2.469D
• Wikipedia: Triphenyl_phosphate
• Wikidata: Q418573
• Metabolomics Workbench ID: 55065
• ChEMBL ID: CHEMBL454511
• Mol file: 115-86-6.mol

Synonyms:triphenyl phosphate

Chemical Property of Triphenyl phosphate

Chemical Property:

• Appearance/Colour: colourless crystals
• Vapor Pressure: 1.3 mm Hg ( 200 °C)
• Melting Point: 47-53 °C
• Refractive Index: 1.552-1.563
• Boiling Point: 412.4 °C at 760 mmHg
• Flash Point: 201.2 °C
• PSA: 54.57000
• Density: 1.265 g/cm³
• LogP: 5.33150
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble0.0019g/L at 20°C
• Water Solubility.: insoluble
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 326.07079595
• Heavy Atom Count: 23
• Complexity: 325

Purity/Quality:

99% min ^*data from raw suppliers

Triphenyl phosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N,Xn,F
• Hazard Codes: Xn,N,F,Xi
• Statements: 22-38-40-48/20/22-50/53-52/53-36/37/38-67-66-36-11-51/53
• Safety Statements: 36/37-61-60-24/25-22-36-26-16-24-9

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organophosphates, Other
• Canonical SMILES: C1=CC=C(C=C1)OP(=O)(OC2=CC=CC=C2)OC3=CC=CC=C3
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.
• Effects of Long Term Exposure: The substance may have effects on the peripheral nervous system. This may result in impaired functions.
• General Description: Triphenyl phosphate (TPP) is a triaryl phosphate compound synthesized catalytically from white phosphorus and phenols under aerobic conditions using iron catalysts and iodine, offering an environmentally friendly alternative by avoiding chlorine-based processes and acid waste generation. The synthesis is optimized for high selectivity and full conversion, with reaction progress and product composition monitored via advanced analytical techniques such as 31P NMR, HPLC-MS, and GC-MS.

Technology Process of Triphenyl phosphate

There total 104 articles about Triphenyl phosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.8%

triphenyl phosphite (101-02-0) + phosphorous acid trimethyl ester (121-45-9) → phosphoric acid triphenyl ester (115-86-6) + dimethyl phenylphosphonite (18351-42-3) + diphenyl methylphosphonate (7526-26-3) + phenol (108-95-2,27073-41-2)

Guidance literature:

triphenyl phosphite; methyl iodide; at 20 - 240 ℃;

phosphorous acid trimethyl ester; at 210 - 260 ℃; for 4h; Product distribution / selectivity;

Reference yield: 6.7%

trichloromethylphosphonous dichloride (3582-11-4) + phenol (108-95-2,27073-41-2) → triphenyl phosphite (101-02-0) + chloroform (67-66-3,8013-54-5) + phosphoric acid triphenyl ester (115-86-6)

Guidance literature:

Reference yield:

C26H35O9P3S2 (65007-97-8) → sulfotep (3689-24-5) + phosphoric acid triphenyl ester (115-86-6) + C22H25O6P2S(1+)*C4H10BF3O3PS(1-)

Guidance literature:

With boron trifluoride diethyl etherate; at -80 - -60 ℃; Product distribution;

upstream raw materials:

triphenyl phosphite

bromobenzene

diphenylether

diphenyl sulfite

Downstream raw materials:

Triphenylphosphine oxide

phenol

ethyl diphenyl phosphate

benzoic acid phenyl ester

Refernces

Catalytic synthesis of triaryl phosphates from white phosphorus

10.1002/ejic.201100046

The research focuses on the catalytic synthesis of triaryl phosphates, specifically triphenyl phosphate, tritolyl phosphate, and tris(2,4-di-tert-butyl)phenyl phosphate, from white phosphorus and phenols under aerobic conditions. The process is catalyzed by iron catalysts and iodine, achieving full conversion to phosphates without the use of chlorine, thus avoiding acid waste production. The experiments involved various reactants, including different phenols, white phosphorus, iron(III) diketonates as catalysts, and iodine. The reactions were conducted at specific temperatures, with controlled addition rates of white phosphorus and air bubbling to ensure aerobic conditions. The analyses used to monitor the reaction progress and product composition included 31P NMR spectroscopy, HPLC-MS, GC-MS, and in some cases, infrared spectroscopy and mass spectrometry. These techniques allowed for the identification of intermediates and final products, as well as the optimization of reaction conditions for high selectivity towards the desired triaryl phosphates.