63581-66-8

Basic information

• Product Name: Phosphonic acid, (phenylmethyl)-, monomethyl ester
• CAS NO: 63581-66-8
• Molecular Formula: C8H11O3P
• Molecular Weight: 186.147
• Mol File: 63581-66-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Phosphonic acid, (phenylmethyl)-, monomethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonic acid, (phenylmethyl)-, monomethyl ester(63581-66-8)
• EPA Substance Registry System: Phosphonic acid, (phenylmethyl)-, monomethyl ester(63581-66-8)

Safety Data

• Hazardous Substances Data: 63581-66-8(Hazardous Substances Data)

Upstream product

• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 1850-14-2 tetramethoxymethane 
• 6881-57-8 benzylphosphonic acid 
• 1445-45-0 Trimethyl orthoacetate 
• 773-47-7 dimethyl benzylphosphonate 
• 67-56-1 methanol 
• 80642-97-3 C₇H₉O₆PS*2H₃N 
• 186581-53-3 diazomethane 

Downstream Products

• 144108-14-5 Methyl D-2-<(benzylhydroxyphosphoryl)oxy>-2-phenylacetate 
• 945934-00-9 benzylphosphonic acid 2-(tert-butoxycarboxamido)ethyl methyl ester 
• 252554-83-9 hydroxonium-bis(μ-oxo)-μ-benzylmethoxophosphonato-κO:κO'-bis[trichloroantimony(V)] 
• 144108-12-3 benzylphosphonic acid isopropyl ester 
• 144108-13-4 Methyl D-2-<(benzylhydroxyphosphoryl)oxy>-3-phenylpropionate 
• 18933-98-7 benzylphosphonic acid monoethyl ester 
• 945934-02-1 benzylphosphonic acid 2-(tert-butoxycarboxamido)ethyl ester 

Relevant articles and documents

Selective esterification of phosphonic acids

Here, we report straightforward and selective synthetic procedures for mono-and diesteri-fication of phosphonic acids. A series of alkoxy group donors were studied and triethyl orthoacetate was found to be the best reagent as well as a solvent for the performed transformations. An important temperature effect on the reaction course was discovered. Depending on the reaction temperature, mono-or diethyl esters of phosphonic acid were obtained exclusively with decent yields. The sub-strate scope of the proposed methodology was verified on aromatic as well as aliphatic phosphonic acids. The designed method can be successfully applied for small-and large-scale experiments without significant loss of selectivity or reaction yield. Several devoted experiments were performed to give insight into the reaction mechanism. At 30?C, monoesters are formed via an intermediate (1,1-diethoxyethyl ester of phosphonic acid). At higher temperatures, similar intermediate forms give diesters or stable and detectable pyrophosphonates which were also consumed to give diesters.31P NMR spectroscopy was used to assign the structure of pyrophosphonate as well as to monitor the reaction course. No need for additional reagents and good accessibility and straightforward purification are the important aspects of the developed protocols.

Palladium(II)-catalyzed ortho-arylation of benzylic phosphonic monoesters using potassium aryltrifluoroborates

The new monophosphonic acid directing group was successfully utilized in the Pd (II)-catalyzed ortho-arylation of benzylic phosphonic monoesters using potassium aryltrifluoroborates. A wide range of benzylic phosphonic monoesters underwent clean ortho-ary

The Synthesis of Phosphonate Esters, an Extension of the Mitsunobu Reaction

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