71360-04-8

Basic information

• Product Name: Phosphine oxide, bis(2-methoxyphenyl)-
• CAS NO: 71360-04-8
• Molecular Formula: C14H15O3P
• Molecular Weight: 262.245
• Mol File: 71360-04-8.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Phosphine oxide, bis(2-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphine oxide, bis(2-methoxyphenyl)-(71360-04-8)
• EPA Substance Registry System: Phosphine oxide, bis(2-methoxyphenyl)-(71360-04-8)

Safety Data

• Hazardous Substances Data: 71360-04-8(Hazardous Substances Data)

Usage

General Description

Phosphine oxide, bis(2-methoxyphenyl)-, also known as diphenylphosphoryl-2-methoxyphenylphosphine oxide, is a chemical compound with the formula C14H15O2P. It is a white solid commonly used as a flame retardant and as a stabilizer for plastics and polymers. Phosphine oxide, bis(2-methoxyphenyl)- is also utilized in the production of various organic and pharmaceutical compounds. As a phosphine oxide, it acts as a strong electron acceptor and can participate in a variety of organic reactions such as cross-coupling reactions and catalytic processes. Additionally, it can also be used as a radical scavenger in some chemical processes. Overall, phosphine oxide, bis(2-methoxyphenyl)- is an important and versatile chemical compound with various industrial and research applications.

Upstream product

• 762-04-9 phosphonic acid diethyl ester 
• 31600-86-9 2-methoxyphenyllithium 
• 578-57-4 2-bromoanisole 
• 766-51-8 2-Chloroanisole 
• 16750-63-3 2-methoxyphenylmagnesium bromide 

Downstream Products

• 116163-96-3 1,3-bis[di(2-methoxyphenyl)-phosphino]propane 
• 1370406-93-1 1,3-bis[bis(2-methoxyphenyl)phosphono]propane 

Relevant articles and documents

Synthesis and Reactivity of Palladium(II) Alkyl Complexes that Contain Phosphine-cyclopentanesulfonate Ligands

The synthesis of the phosphine-cyclopentanesulfonate pro-ligands Li/K[2-PPh2-cyclopentanesulfonate] (Li/K[2a]), Li/K[2-P(2-OMe-Ph)2-cyclopentanesulfonate] (Li/K[2b]), and H[2b], and the corresponding Pd(II) alkyl complexes (κ2-P,O-2a)PdMe(pyridine) (3a) and (κ2-P,O-2b)PdMe(pyridine) (3b) is described. The sulfonate-bridged base-free dimer {(2b)PdMe}2 (4b) was synthesized by abstraction of pyridine from 3b using B(C6F5)3. The borane-coordinated base-free dimer [{2b·B(C6F5)3}PdMe]2 (5b), in which B(C6F5)3 binds to a sulfonate oxygen, was prepared by addition of 1 equiv of B(C6F5)3 per Pd to 4b or addition of 2 equiv of B(C6F5)3 to 3b. Compounds 3b, 4b, and 5b polymerize ethylene with low activity (up to 210 kg mol-1 h-1 at 250 psi and 80 °C) to linear polyethylene (Mn = 1950-5250 Da) with predominantly internal olefin placements. 3b and 4b copolymerize ethylene with methyl acrylate to linear copolymers that contain up to 11.7 mol % methyl acrylate, which is incorporated as -CH2CH(CO2Me)CH2- (80%) in-chain units and -CH2CH(CO2Me)Me (8%) and -CH2CH-CH(CO2Me) (12%) chain-end units. 3b and 4b also copolymerize ethylene with vinyl fluoride to linear copolymers that contain up to 0.41 mol % vinyl fluoride, which is incorporated as -CH2CHFCH2- (～80%) in-chain units and -CH2CF2H (7%), -CH2CHFCH3 (5%), and -CH2CH2F (8%) chain-end units. Complexes 3b and 4b are more stable and active in ethylene polymerization than analogous (PAr2-CH2CH2SO3)PdR catalysts, but are less active than analogous (PAr2-arenesulfonate)PdR catalysts. Low-temperature NMR studies show that 4b reacts with ethylene below -10 °C to form the ethylene adduct cis-P,R-(2b)PdMe(ethylene) (7b), which undergoes ethylene insertion at 5 °C. DFT calculations for a model (PMe2-cyclopentanesulfonate)Pd(Pr)(ethylene) species show that ethylene insertion proceeds by cis-P,R/trans-P,R isomerization followed by migratory insertion, and that the lower activity of 3b and 4b vis-à-vis analogous (PAr2-arenesulfonate)PdR catalysts results from a higher barrier for migratory insertion of the trans-P,R isomer.

Method for synthesizing bis(2-methoxyphenyl) phosphine oxide

The invention belongs to the technical field of fine chemical industry, and particularly relates to a method for synthesizing bis(2-methoxyphenyl) phosphine oxide. The method comprises the following steps: a) carrying out a reaction of anisole and triethyl phosphate in a solvent to obtain ethyl bis(2-methoxyphenyl)phosphonate; and b) performing hydrogenation reduction on ethyl bis(2-methoxyphenyl)phosphonate in a solvent to obtain bis(2-methoxyphenyl) phosphine oxide. The method uses anisole as a starting raw material, first the reaction of anisole and triethyl phosphate is carried out to obtain ethyl bis(2-methoxyphenyl)phosphonate, and then hydrogenation reduction is carried out to synthesize bis(2-methoxyphenyl) phosphine oxide. The method has simple reaction, high conversion rate, andexcellent product quality. The content of bis(2-methoxyphenyl) phosphine oxide produced by the method is 98% or more, technical requirements for producing related polyketone ligands in the market aremet, the operation steps are simple, required equipment is simple, and energy consumption is low.

Rapid Metal-Free Formation of Free Phosphines from Phosphine Oxides

A rapid method for the reduction of secondary phosphine oxides under mild conditions has been developed, allowing simple isolation of the corresponding free phosphines. The methodology involves the use of pinacol borane (HBpin) to effect the reduction while circumventing the formation of a phosphine borane adduct, as is usually the case with various other commonly used borane reducing agents such as borane tetrahydrofuran complex (BH3?THF) and borane dimethyl sulfide complex (BH3?SMe2). In addition, this methodology requires only a small excess of reducing agent and therefore compares favourably not just with other borane reductants that do not require a metal co-catalyst, but also with silane and aluminium based reagents. (Figure presented.).