20039-33-2

Usage

Uses

Used in Organic Synthesis:
Diethoxyphosphinyl Isocyanate is used as an intermediate in organic synthesis for the production of various chemical compounds.
Used in Electrolyte Additives for Batteries:
Diethoxyphosphinyl Isocyanate is used as a film-forming electrolyte additive in propylene carbonate (PC) and EC/EMC-based electrolytes, enhancing the performance and stability of batteries.

Preparation

A solution of diethyl phosphoramidate (30.6 g, 0.2 mol) in tetrachloromethane (50 mL) was slowly added dropwise with stirring and efficient external cooling to a solution of oxalyl chloride (27.9 g, 0.22 mol) in the same solvent (150 mL). The reaction temperature was kept at -5 to 0 °C. After completion of the addition, the temperature of the mixture was slowly increased to 50 °C and this was maintained for 1 h. The mixture was then cooled to room temperature, filtered, and concentrated in vacuo. The residual liquid product was distilled in vacuo (bp 85–87 °C/10 Torr); yield 22.9 g (64%).

InChI:InChI=1/C5H10NO4P/c1-3-9-11(8,6-5-7)10-4-2/h3-4H2,1-2H3

Upstream product

• 79-37-8 oxalyl dichloride 
• 1068-21-9 Diethyl phosphoramidate 
• 18368-11-1 diethyl N,N-dichlorophosphoroamidate 
• 61351-37-9 C₄HCl₄NO₃ 
• 122-52-1 triethyl phosphite 
• 31334-44-8 diethyl isocyanatophosphite 
• 3135-78-2 Ureidophosphorsaeurediethylester 
• 141-97-9 ethyl acetoacetate 
• 15586-25-1 methyl chloromethylcarbamate 
• 287411-39-6 C₉H₂₀NO₈PS 
• 6185-96-2 dichloromethylene-phosphoramidic acid diethyl ester 
• 75-44-5 phosgene 

Downstream Products

• 66475-34-1 C₁₃H₂₁N₄O₅P 
• 66475-29-4 C₁₆H₂₇N₄O₅P 
• 66475-10-3 N,N'-Bis-(N-diethoxyphosphoryl-carbamoyl)-o-phenylendiamin 
• 66475-11-4 C₁₆H₂₈N₄O₇P₂S 
• 66475-12-5 N-(Diethoxyphosphorylcarbamoyl)-N'-(diethoxy-thiophosphoryl-thiocarbamoyl)-o-phenylendiamin 
• 66475-31-8 C₁₉H₂₅N₄O₆P 
• 33202-91-4 (N'-Phenyl-ureido)-phosphorsaeurediethylester 
• 66475-18-1 N-(2-Aminophenyl)-N'-(diethoxyphosphoryl)-harnstoff 
• 28833-20-7 C₂₃H₂₆N₂O₄P₂ 
• 37594-00-6 C₁₁H₁₆N₃O₆P 
• 64688-97-7 (2,2,2-Trimethoxy-5-phenyl-2λ⁵-[1,3,2]dioxaphosphole-4-carbonyl)-phosphoramidic acid diethyl ester 
• 132270-93-0 (N'-Cyclohexyl-ureido)-phosphorsaeurediethylester 
• 132270-91-8 -phosphorsaeurediethylester 
• 132270-90-7 -phosphorsaeurediethylester 

Relevant academic research and scientific papers

Regio- And diastereoselective Pd-catalyzed aminochlorocyclization of allylic carbamates: scope, derivatization, and mechanism

The regio- and diastereoselective synthesis of oxazolidinonesviaa Pd-catalyzed vicinal C-N/C-Cl bond-forming reaction from internal alkenes of allylic carbamates is reported. The oxazolidinones are obtained in yields of 44 to 95% with high to excellent diastereoselectivities (from 6?:?1 to >20?:?1 dr) from readily available precursors. This process is scalable, and the products are suitable for the synthesis of useful amino alcohols. A detailed theoretical and experimental mechanistic study was carried out to describe that the reaction proceeds through ananti-aminopalladation of the alkene followed by an oxidative C-Pd(ii) cleavage with retention of the carbon stereochemistry to yield the major diastereomer. The role of Cu(ii) in a C-Cl bond-forming mechanism step has also been proposed.

On the route to the N-phosphoryl sulfamic acid

Synthesis of the previously unknown N-diethyl phosphorosulfamate 15 was accomplished by direct sulfamation of diethyl phosphoroamidate 4 with sulfur trioxide-DMF complex 14. The acid 15 was isolated in form of benzyl-16 and cyclohexylammonium 17 salts, which were found to be unstable in water solution. The other possible routes to sulfamate 15 were briefly tested.

Synthesis of N,N'-Bis(diethylphosphoryl) Sulfamide

The reaction of phosphoroamidates 5a-c with an excess of sulfuryl chloride, as well as the reaction of 5a with sulfur trioxide were investigated. In both reactions, the formation of a new type of phosphoroorganic compound namely, N,N'-bis(diethylphosphoryl) sulfamide (6) was observed. This unexpected reaction pathway is rationalized as a result of the formation of dialkyl phosphorosulfonyl amide 3, a reactive common intermediate in both processes.

Organic Phoshorus Compounds. XVI. On the Chemistry of the Isocyanatophosphoric Acid Diethyl Ester

A one-pot procedure for preparing ureidophosphoric acid dialkyl esters 2 from POCl3, urea, and alcohols via ureidophosphoric acid dichloride 1 was worked out. 2 (R=Et) was used as starting material for isocyanatophosphoric acid diethyl ester (4, R=Et), th

Phosphonoureide and phosphonothioureide anthelmintics

This invention relates to novel anthelmintic compounds containing an arylene or divalent heterocyclic ring whose free valences are satisfied by 1. a disubstituted phosphoryl ureido or thioureido group and 2. an amino group or a substituted amido or thioamido group, To compositions containing them, and to methods of using them for the treatment of intestinal parasites in mammals and birds.