72696-92-5

Upstream product

• 79782-58-4 β-(N-benzyl)aminoethylphosphonic acid diethyl ester 
• 72696-77-6 {2-[Benzyl-(diethoxy-phosphoryl)-amino]-ethyl}-phosphonic acid diethyl ester 
• 16672-87-0 2-chloroethylphosphonic acid 
• 100-46-9 benzylamine 
• 100-39-0 benzyl bromide 
• 1415210-80-8 C₁₅H₃₀NO₃PSi₂ 

Downstream Products

• 2041-14-7 (2-aminethyl)phosphonic acid 

Relevant academic research and scientific papers

Synthesis of 2-(arylamino)ethyl phosphonic acids via the aza-Michael addition on diethyl vinylphosphonate

A simple way of synthesising 2-(arylamino)ethyl phosphonic esters and acids via the aza-Michael addition of amines to diethyl vinylphoshonate 'on water' was developed. Various 2-(arylamino)ethyl phosphonates were initially produced through the condensation of primary and secondary amines with diethyl vinylphosphonate, focussing on those bearing one aromatic moiety, giving generally good to high yields (i.e.; 75-100%). These phosphonic esters were then hydrolysed in presence of bromomethylsilane to give quantitatively the corresponding phosphonic acids.

A new simple route to N-substituted 2-aminoethylphosphonic acids

2-Aminoethylphosphonic acid (AEPA) and its N-substituted compounds were prepared by one step reaction using 2-chloroethylphosphonic acid with ammonia and amines (H2NMe, HNMeMe, HNEtEt, H2NPr-n, H2NCH2ph,H2NCH2CH2NH2 and H2N(C=NH)NH2 in a dilute alkaline solution below 20 °C with simple work- up and easy purification. The reaction was accelerated by catalytic amount of potassium iodide. The yield for the reaction products were 35.6 to 48.6% for the KI absence and 78.2 to 88.0% for the KI presence.

Aminobenzylation d'aldehydes phosphoniques: preparation d'acides aminoalkylphosphoniques

The reaction of phosphonic aldehydes with benzylamine in presence of NaBH3CN yields benzylaminoalkylphosphonates which, submitted to catalytic hydrogenation, lead to phosphonic amino esters.When reductive amination is carried out with H2/Pd reduction and debenzylation are observed simultaneously.In the absence of reducing agent the enaminobenzylphosphonate can be isolated and N-alkylated.Hydrolysis of phosphonic amino-esters with dilute HCl gives phosphonic amino acids.The order of occurence of each operation, as well as the choice of the catalyst is discussed.