79782-58-4

Basic information

• Product Name: Phosphonic acid, [2-[(phenylmethyl)amino]ethyl]-, diethyl ester
• CAS NO: 79782-58-4
• Molecular Formula: C13H22NO3P
• Molecular Weight: 271.296
• Mol File: 79782-58-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Phosphonic acid, [2-[(phenylmethyl)amino]ethyl]-, diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonic acid, [2-[(phenylmethyl)amino]ethyl]-, diethyl ester(79782-58-4)
• EPA Substance Registry System: Phosphonic acid, [2-[(phenylmethyl)amino]ethyl]-, diethyl ester(79782-58-4)

Safety Data

• Hazardous Substances Data: 79782-58-4(Hazardous Substances Data)

Upstream product

• 682-30-4 Diethyl vinylphosphonate 
• 100-46-9 benzylamine 
• 1606-75-3 (2-oxoethyl)phosphonic acid diethyl ester 

Downstream Products

• 206648-63-7 N-Benzyl-N-(2,3-dioxo-7-nitro-1,2,3,4-tetrahydroquinoxalin-5-ylmethyl)-α-aminoethanephosphonic acid 
• 870544-50-6 C₂₂H₃₄NO₇P 
• 122954-42-1 β-(N-benzyl)aminoethylphosphonic acid hydrochloride 
• 72696-92-5 acide N-benzylamino-2 ethylphosphonique 
• 41468-36-4 diethyl (2-aminoethyl)phosphonate 
• 122954-41-0 N-benzyl-N-<β-(diethoxyphosphonyl)ethyl>-2,3,5,6-tetramethylphenylacetamidoxime 
• 122954-26-1 {2-[Benzyl-(dipropoxy-phosphanyl)-amino]-ethyl}-phosphonic acid diethyl ester 
• 122954-24-9 {2-[Benzyl-(diethoxy-phosphanyl)-amino]-ethyl}-phosphonic acid diethyl ester 
• 1415210-80-8 C₁₅H₃₀NO₃PSi₂ 
• 122954-40-9 N-benzyl-N-<β-(diethoxyphosphonyl)ethyl>mesitylacetamidoxime 

Relevant articles and documents

Exploring Partners for the Domino α-Arylation/Michael Addition Reaction Leading to Tetrahydroisoquinolines

Sulfonates, sulfonamides, and phosphonates have proven useful nucleophiles for palladium-catalyzed intramolecular α-arylation reactions leading to tetrahydroisoquinolines. Although the sulfonate α-arylation reaction can be successfully combined in a domino process with a broad range of Michael acceptors, only vinyl sulfones can be used in Michael additions when starting from sulfonamides. No domino process was developed with the phosphonate derivative. DFT calculations were carried out to gain more insights into the experimental differences observed in the reactions involving these substrates.

A practical and efficient green synthesis of β-aminophosphoryl compounds via the aza-michael reaction in water

Application of water as a solvent (without any cosolvent) promotes the aza-Michael reaction of diethyl vinylphosphonate and diphenylvinylphosphine oxide with a wide range of N-nucleophiles. The solubility of the starting phosphorus substrate in water does not play a crucial role in the reaction course, decreasing to some extent the reaction rate. The reaction can be performed either at room temperature or under reflux to afford the corresponding β-aminophosphonates and β-aminophosphine oxides in excellent yields and of high purity via a simple freeze-drying isolation procedure. Application of basic catalysts makes possible the addition of weak nucleophiles such as a-amino acids and their phosphorus analogues; that is, a-aminophosphonic acids. The aqueous aza-Michael reaction allowed us to easily perform double phosphorylation of primary amines including polyamines using a reactant ratio (phosphorus substrate: amine) of 2:1. Copyright Taylor & Francis Group, LLC.

Efficient synthesis of racemic β-aminophosphonates via aza-Michael reaction in water

Water as a solvent significantly accelerates the addition of various amines to diethyl vinylphosphonate to yield β-aminophosphonates without any catalyst compared to known procedures for such aza-Michael reactions. The products are obtained in quantitative yields and high purity over short reaction times. Using a reactant ratio (vinylphosphonate/amine) of 2:1 resulted in double phosphorylation of primary amines.