2511-19-5

Basic information

• Product Name: DIMETHYL ETHYLPHOSPHONITE
• Synonyms: AURORA KA-1301;DIMETHYL ETHYLPHOSPHONITE;DIMETHYL ETHANEPHOSPHONITE;ETHANEPHOSPHONOUS ACID DIMETHYL ESTER;dimethylphosphinic acid ethyl ester
• CAS NO: 2511-19-5
• Molecular Formula: C₄H₁₁O₂P
• Molecular Weight: 122.1
• Product Categories: Phosphorus compounds
• Mol File: 2511-19-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 73-75°C 2,5mm
• Flash Point: 46.4 °C
• Appearance: /
• Density: 0,952 g/cm3
• Vapor Pressure: 12.6mmHg at 25°C
• Refractive Index: 1.383
• CAS DataBase Reference: DIMETHYL ETHYLPHOSPHONITE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL ETHYLPHOSPHONITE(2511-19-5)
• EPA Substance Registry System: DIMETHYL ETHYLPHOSPHONITE(2511-19-5)

Safety Data

• Statements: 20/21/22
• Safety Statements: 23-36
• RIDADR: 3278
• Hazardous Substances Data: 2511-19-5(Hazardous Substances Data)

Usage

General Description

Dimethyl ethylphosphonite, also known as DMPO, is a chemical compound with the molecular formula C4H11O2P. It is a colorless liquid that is used as a solvent and as a precursor in the synthesis of organophosphorus compounds. DMPO is commonly employed as a reactive diluent in the manufacturing of epoxy resins and as a flame retardant additive in plastics and polymers. It is also used as a stabilizer in organic peroxide formulations. DMPO is toxic when ingested or inhaled and can cause irritation to the eyes, skin, and respiratory system. It is important to handle and store DMPO in a well-ventilated area and to use appropriate safety precautions when working with this chemical.

InChI:InChI=1/C4H11O2P/c1-4-6-7(2,3)5/h4H2,1-3H3

Upstream product

• 64-17-5 ethanol 
• 59581-57-6 3-nitrophenyl dimethylphosphinate 
• 59581-58-7 4-acetylphenyl dimethylphosphinate 
• 59581-60-1 4-chlorophenyl dimethylphosphinate 
• 59581-62-3 4-methylphenyl dimethylphosphinate 
• 57244-61-8 phenyl dimethylphosphinate 
• 13344-08-6 p-nitrophenyl dimethyl phosphinate 

Downstream Products

• 356074-17-4 B(C₆F₅)3(CH₃CH₂O)(CH₃)2PO 

Relevant articles and documents

Nucleophilic displacement on 4-nitrophenyl dimethyl phosphinate by ethoxide ion: Alkali metal ion catalysis and mechanism

We report on a spectrophotometric kinetic study of the effect of Li + and K- cations on the ethanolysis of 4-nitrophenyl dimethylphosphinate (4a) in ethanol at 25°C. The nucleophilic displacement reaction of 4a with LiOEt and KOEt in the absence and presence of 18-crown-6 ether (18-C-6) furnished observed first-order rate constants which increase in the order EtO-MOEt. Derived δG ip, δGts and ΔGcat values quantify ground state and transition state stabilization by the metal ions to give δGtn>δGip for Li+ and δGts～δGip for K+. These results indicate moderate catalysis by Li+, with 4a manifesting lesser susceptibility to catalysis than other substrates previously studied. Second-order rate constants for the reaction of the aryl dimethylphosphinates 4a-f with free EtO- were obtained from plots of log kobs vs. [KOEt], measured in the presence of excess 18-C-6. Hammett plots with σ and σ° substituent constants give significantly better correlation of rates than σ- and yield a moderately large ρ(ρ°) value; this is interpreted in terms of a stepwise mechanism involving rate-limiting formation of a pentacoordinate intermediate. Comparison of the present results with those of Williams on the aqueous alkaline hydrolysis of Me2P(O)-OPhX and Ph2P(O)-OPhX esters, establishes the rationale for a change in mechanism in the more basic EtO/EtOH nucleophile/solvent system by a stepwise mechanism instead of a concerted one in aqueous base. Structure-reactivity correlations following Jencks show that the change in mechanism is accounted for by cross interactions between the nucleophile and the leaving group in the transition state. The observed duality of mechanism is rationalized on the basis of the More O'Ferrall-Jencks diagram, as a spectrum of transition states covering a wide range of nucleophile and leaving group basicities.