115-88-8

Basic information

• Product Name: diphenyl octyl phosphate
• Synonyms: Octyl phenyl phosphate;Phosphoric acid, octyl diphenyl;Phosphoric acid diphenyl=octyl ester;Phosphoric acid diphenyloctyl ester
• CAS NO: 115-88-8
• Molecular Formula: C₂₀H₂₇O₄P
• Molecular Weight: 286.303781
• EINECS: 204-113-8
• Mol File: 115-88-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 425.5 °C at 760 mmHg
• Flash Point: 224.6 °C
• Appearance: /
• Density: 1.1050 (rough estimate)
• Vapor Pressure: 4.71E-07mmHg at 25°C
• Refractive Index: 1.5230 (estimate)
• Water Solubility: 0.14mg/L(24 oC)
• CAS DataBase Reference: diphenyl octyl phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: diphenyl octyl phosphate(115-88-8)
• EPA Substance Registry System: diphenyl octyl phosphate(115-88-8)

Safety Data

• Hazardous Substances Data: 115-88-8(Hazardous Substances Data)

Usage

Uses

Octyl phenyl phosphate is a phosphorus flame retardant additive.

General Description

Octyl phenyl acid phosphate is a colorless liquid. diphenyl octyl phosphate is corrosive to the skin, eyes, and mucous membranes.

Reactivity Profile

Organophosphates, such as OCTYL PHENYL ACID PHOSPHATE, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.

InChI:InChI=1/C20H27O4P/c1-2-3-4-5-6-13-18-22-25(21,23-19-14-9-7-10-15-19)24-20-16-11-8-12-17-20/h7-12,14-17H,2-6,13,18H2,1H3

Synthetic route

octanol (111-87-5) + chlorophosphoric acid diphenyl ester (2524-64-3) → diphenyl hydrogenphosphate (115-88-8)

Conditions	Yield
With titanium tetrachloride; triethylamine In tetrahydrofuran at 20℃; for 1h;	94%
With titanium(IV) tetrabutoxide; triethylamine In dichloromethane at 20℃; for 1h;	92%
With pyridine

octanol (111-87-5) + diphenyl phosphoryl azide (26386-88-9) → diphenyl hydrogenphosphate (115-88-8)

Conditions	Yield
With sodium carbonate In cyclohexane at 80℃; for 24h; Schlenk technique;	83%

diphenyl hydrogen phosphate (838-85-7) + octanol (111-87-5) → diphenyl hydrogenphosphate (115-88-8)

Conditions	Yield
With copper(l) iodide; sodium carbonate; triethylamine In tetrachloromethane at 80℃; for 12h;	82%

2-octyloxy-benzooxazole (66910-83-6) + diphenyl hydrogen phosphate (838-85-7) → diphenyl hydrogenphosphate (115-88-8)

diphenyl hydrogen phosphate (838-85-7) + octanol (111-87-5) + ethyl (E)-3-(2-furyl)prop-2-enoate (623-20-1) → diphenyl hydrogenphosphate (115-88-8) + (E)-3-Furan-2-yl-acrylic acid octyl ester (101100-85-0) + mono-octyl phenyl phosphoric acid (10581-14-3) + diphenyl 3-(2-furyl) acrylyl phosphate (140138-20-1)

Conditions	Yield
potassium carbonate In dodecane for 3h; Product distribution; various cat.;

diphenyl hydrogen phosphate (838-85-7) + octanol (111-87-5) + ethyl (E)-3-(2-furyl)prop-2-enoate (623-20-1) → diphenyl hydrogenphosphate (115-88-8) + (E)-3-Furan-2-yl-acrylic acid octyl ester (101100-85-0) + diphenyl 3-(2-furyl) acrylyl phosphate (140138-20-1)

Conditions	Yield
potassium carbonate at 143℃; for 3h;

octyl phosphorodichloridate (53121-41-8) + aqueous sodium phenolate solution → diphenyl hydrogenphosphate (115-88-8)

octanol (111-87-5) → diphenyl hydrogenphosphate (115-88-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2; petroleum ether / 30 h / Ambient temperature View Scheme

octylmagnesium bromide (17049-49-9) + chlorophosphoric acid diphenyl ester (2524-64-3) → diphenyl hydrogenphosphate (115-88-8)

Conditions	Yield
In diethyl ether at 20℃; for 12h;

diphenyl hydrogenphosphate (115-88-8) + tert-butyl 2-(bromomethyl)acrylate (53913-96-5) → tert-butyl 2-methyleneundecanoate (143238-83-9)

Conditions	Yield
Yield given. Multistep reaction;

Upstream product

• 111-87-5 octanol 
• 17049-49-9 octylmagnesium bromide 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 26386-88-9 diphenyl phosphoryl azide 
• 838-85-7 diphenyl hydrogen phosphate 
• 53121-41-8 octyl phosphorodichloridate 
• 53282-12-5 ethyl (E)-3-(2-furyl)prop-2-enoate 
• 66910-83-6 2-octyloxy-benzooxazole 

Relevant articles and documents

A high-performance impregnated resin for recovering thorium from radioactive rare earth waste residue

A novel impregnated resin with n-octyl diphenyl phosphate (ODP-IR) was developed for the separation of thorium from leaching solution of rare earth (RE) waste residue. Nitrogen adsorption, FT-IR spectra, scanning electron microscopy and energy dispersive spectrometer were conducted for the characterization of ODP-IR. Uptake of ODP-IR for Th4?+ was significantly affected by changing HNO3 concentration. The adsorption data were fitted well with pseudo-second-order rate model. Thermodynamic parameters for the adsorption of Th4?+ were calculated and discussed. The adsorption was fitted well with the Langmuir isotherm model than Freundlich isotherm model. ODP-IR was repeatedly used five times without obvious loss for Th4?+ adsorption, indicating that the adsorbent was stabilized. The ODP-IR was successfully used to separate Th from RE and Fe using the feed solution from ion-adsorption type RE waste residue, which revealed potentials in the fields of RE resource utilization, radioactive contamination treatment and nuclear fuel preparation.

Direct aerobic oxidative esterification and arylation of P(O)-OH compounds with alcohols and diaryliodonium triflates

Copper-catalyzed aerobic oxidative esterification of P(O)-OH compounds is achieved using alcohols as efficient esterification reagents, giving the expected products with good to moderate yields. Furthermore, it is shown that the arylation of P(O)-OH compounds proceeds efficiently to produce the corresponding products via the treatment of diaryliodonium triflates under mild reaction conditions. It is a simple way to produce a broad spectrum of functionalized phosphinates, phosphonates, and phosphates from basic starting materials with good to excellent yields. The protocol is convenient for practical application. A plausible mechanism has been proposed for the reaction.

A simple and effective method for phosphoryl transfer using TiCl4 catalysis

(graph presented) A number of Lewis acids have been evaluated as catalysts for the phosphoryl transfer, the most efficient being TiCl4. Application of this methodology to the phosphorylation of a number of representative target alcohols is presented.