20030-44-8

Basic information

• Product Name: Phosphonic acid, oxiranyl-, diethyl ester
• Synonyms: oxiranyl-phosphonic acid diethyl ester;epoxy-1,2 ethyl phosphonate de diethyle;Diethylepoxyethylphosphonat;2-diethoxyphosphoryl-oxirane;Phosphonic acid,oxiranyl-,diethyl ester;diethyl 1,2-epoxyethanephosphonate;diethyl epoxyethylphosphonate;diethyl 2-oxiranylphosphonate;diethyl 1,2-epoxyethylphosphonate
• CAS NO: 20030-44-8
• Molecular Formula: C6H13O4P
• Molecular Weight: 180.141
• Mol File: 20030-44-8.mol

Chemical Properties

• Boiling Point: 80 °C(Press: 0.9 Torr)
• Density: 1.16±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Phosphonic acid, oxiranyl-, diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonic acid, oxiranyl-, diethyl ester(20030-44-8)
• EPA Substance Registry System: Phosphonic acid, oxiranyl-, diethyl ester(20030-44-8)

Safety Data

• Hazardous Substances Data: 20030-44-8(Hazardous Substances Data)

Upstream product

• 682-30-4 Diethyl vinylphosphonate 
• 65345-03-1 bromo-1 hydroxy-2 ethyl phosphonate de diethyle 
• 65345-02-0 chloro-1 hydroxy-2 ethyl phosphonate de diethyle 
• 75-91-2 tert.-butylhydroperoxide 
• 141-52-6 sodium ethanolate 
• 67-56-1 methanol 

Downstream Products

• 19462-43-2 α-Hydroxy-β-phenylamino-ethylphosphonsaeure-diethylester 
• 20641-57-0 diethyl (2-chloro-1-hydroxyethyl)phosphonate 
• 1262802-47-0 diethyl N-(4-acetylphenyl)-2-oxo-oxazolidin-5-ylphosphonate 
• 1262802-45-8 diethyl N-phenyl-2-oxo-oxazolidin-5-ylphosphonate 
• 1262802-46-9 diethyl N-(4-methoxyphenyl)-2-oxo-oxazolidin-5-ylphosphonate 
• 1262802-48-1 C₁₄H₂₀NO₆P 
• 1206893-55-1 diethyl 2-(N,N-dibenzylamino)-1-hydroxyethanephosphonate 
• 1289220-75-2 diethyl 2-[4-(2,4-difluorophenyl)-1,2,3-triazol-1-yl]-1-hydroxyethylphosphonate 
• 1289220-74-1 diethyl 2-[4-(3-fluorophenyl)-1,2,3-triazol-1-yl]-1-hydroxyethylphosphonate 
• 1289220-73-0 diethyl 2-[4-(2-fluorophenyl)-1,2,3-triazol-1-yl]-1-hydroxyethylphosphonate 
• 1289220-71-8 diethyl 2-[4-(benzoyloxymethyl)-1,2,3-triazol-1-yl]-1-hydroxyethylphosphonate 
• 247137-71-9 [(R)-1-Hydroxy-2-((S)-1-phenyl-ethylamino)-ethyl]-phosphonic acid diethyl ester 
• 247137-73-1 [(R)-1-Hydroxy-2-((R)-1-phenyl-ethylamino)-ethyl]-phosphonic acid diethyl ester 
• 247137-75-3 ((R)-2-Benzylamino-1-hydroxy-ethyl)-phosphonic acid diethyl ester 

Relevant articles and documents

An enantioselective synthesis of (R)-2-amino-1-hydroxyethylphosphonic acid by hydrolytic kinetic resolution of (±)-diethyl oxiranephosphonate

(±)-Diethyl oxiranephosphonate undergoes efficient hydrolytic kinetic resolution by (R,R)-N,N'-bis(3,5-di-tertbutylsalicylidene)-1,2- cyclohexanediaminocobalt(III) acetate; opening of the resultant (R)-epoxide by benzylamine, followed by phosphonate ester hydrolysis and hydrogenolysis, affords the protozoal plasma membrane component (R)-2-amino-1- hydroxyethylphosphonic acid.

Organosilicon compounds with functional groups proximate to silicon. XVII. Synthetic and mechanistic aspects of the lithiation of α,β-epoxyalkylsilanes and related α-heterosubstituted epoxides

A series of α-heterosubstituted epoxides, , has been found to undergo lithiation in the temperature range of -75 to -115 deg C at the C-H bond of the epoxide.The substituent Z could be Me3Si, Ph3Si, n-Bu3Sn, Ph3Sn, PhSO2, (OEt)2PO and Ph; the groups R and R' were H, Ph and n-C6H13; and the lithiating reagents were n-butyllithium, t-butyllithium and lithium diisopropylamide in donor media of THF or TMEDA.The lithiation occurs with retention of configuration and the resulting lithio-epoxide is unstable above 0 deg C, decomposing in a carbenoid manner.The lithiation is facile except for compounds where Z and R (an alkyl or aryl) are cis-oriented; where Z = R3Sn, lithiation occurs by tin-lithium, rather than hydrogen-lithium, exchange.The lithio-epoxides thereby generated can be quenched with various reagents to yield epoxides where the epoxide H has been replaced by D, Me3Sn, R, RCO and COOH.The utility of this procedure in organic synthesis is emphasized.Finally, the possible explanations for the acidity of such α-heterosubstituted epoxides and for the relative stability of the derived lithio-epoxides are considered and assessed.

ETUDE DE LA REACTION DE CYCLISATION DES HALOHYDRINES-1,2 ETHYL PHOSPHONATES DE DIETHYLE POUR L'OBTENTION DE L'EPOXY-1,2 ETHYL PHOSPHONATE DE DIETHYLE

Here we report on the synthesis of the diethyl 1,2-epoxyethylphosphonate 1 from diethyl 1-halogeno 2-hydroxyethylphosphonates 4a and 4b.The halohydrins were prepared by hypohalogenation of the diethyl vinylphosphonate and their structures confirmed by 31P, 1H and 13C NMR spectroscopy.The epoxidation cyclisation was studied using a variety of bases (HNa, KOH, EtO-, K2CO3) and solvents (THF, EtOH, MeOH).In aprotic solvents, there was a competition between the epoxidation cyclisation and a Wittig-Horner type reaction leading to the vinyl chloride.Good yields of the title compound 1 were obtained using the phase transfer catalysed reactions conditions.

1-HYDROXY-2-AMINOETHANEPHOSPHONIC ACID AND DERIVATIVES

Oxirane ring opening in diethyl 1,2-epoxy-1-methylethanephosphonate with ammonia or amines yields products with OH group at position 1 and amino group at position 2.Structural evidence for 1-hydroxy-1-methyl-2-aminoethanephosphonic acid is provided by its conversion to 2-oxo-propanephosphonic acid upon diazotization.Ammonolysis of diethyl 1,2-epoxyethanephosphonate yields the naturally occurring phosphonic analog of isoserine.