40962-37-6

Basic information

• Product Name: methylacetylphosphonate
• Synonyms: methylacetylphosphonate;Acetic acid, phosphono-, 1-methyl ester;Methyl acetyl phosphate
• CAS NO: 40962-37-6
• Molecular Formula: C₃H₇O₅P
• Molecular Weight: 0
• Mol File: 40962-37-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 331.6°C at 760 mmHg
• Flash Point: 154.4°C
• Appearance: /
• Density: 1.529g/cm³
• Vapor Pressure: 2.98E-05mmHg at 25°C
• Refractive Index: 1.461
• CAS DataBase Reference: methylacetylphosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: methylacetylphosphonate(40962-37-6)
• EPA Substance Registry System: methylacetylphosphonate(40962-37-6)

Safety Data

• Hazardous Substances Data: 40962-37-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C3H7O5P/c1-8-3(4)2-9(5,6)7/h2H2,1H3,(H2,5,6,7)

Upstream product

• 1067-74-9 Methyl diethylphosphonoacetate 
• 67-56-1 methanol 
• 65868-40-8 ethyl P,P-bis(trimethylsilyl) phosphonoacetate 
• 4408-78-0 phosphonoacetic acid 
• 485-80-3 S-adenosyl-L-methionine 
• 67605-34-9 methyl 2-(bis((trimethylsilyl)oxy)phosphoryl)acetate 
• 5927-18-4 trimethyl phosphonoacetate 

Downstream Products

• 143140-39-0 methyl 2-cyclobutylideneacetate 
• 88738-78-7 bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate 
• 1280206-23-6 (E)-3-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-acrylic acid methyl ester 
• 870092-45-8 methyl 2-(4-(dimethylamino)-4-phenylcyclohexylidene)acetate 

Relevant articles and documents

Biosynthesis of fosfazinomycin is a convergent process

Fosfazinomycin A is a phosphonate natural product in which the C-terminal carboxylate of a Val-Arg dipeptide is connected to methyl 2-hydroxy-2-phosphono-acetate (Me-HPnA) via a unique hydrazide linkage. We report here that Me-HPnA is generated from phosphonoacetaldehyde (PnAA) in three biosynthetic steps through the combined action of an O-methyltransferase (FzmB) and an α-ketoglutarate (α-KG) dependent non-heme iron dioxygenase (FzmG). Unexpectedly, the latter enzyme is involved in two different steps, oxidation of the PnAA to phosphonoacetic acid as well as hydroxylation of methyl 2-phosphonoacetate. The N-methyltransferase (FzmH) was able to methylate Arg-NHNH2 (3) to give Arg-NHNHMe (4), constituting the second segment of the fosfazinomycin molecule. Methylation of other putative intermediates such as desmethyl fosfazinomycin B was not observed. Collectively, our current data support a convergent biosynthetic pathway to fosfazinomycin.

Facile Two-Step Synthesis of Methyl Bis(2,2,2-trifluoroethyl)phosphonoacetate by Exploiting Garegg-Samuelsson Reaction Conditions

A facile two-step synthesis of methyl bis(2,2,2-trifluoroethyl)phosphonoacetate (Still-Gennari reagent) has been developed by exploiting Garegg-Samuelsson reaction conditions. Starting from trimethyl phosphonoacetate, Still-Gennari reagent was prepared in 94% yield via methyl 2-{bis[(trimethylsilyl)oxy]phosphoryl}acetate intermediate. This synthetic procedure was also used to prepare some kinds of Horner-Wadsworth-Emmons reagents and related compounds.

Dealkylation of phosphonate esters with chlorotrimethylsilane

Chlorotrimethylsilane completely dealkylates phosphonate esters at elevated temperature in a sealed reaction vessel. These conditions are tolerated by a variety of functional groups and lead to high conversions of dimethyl, diethyl and diisopropyl phosphonates to their corresponding phosphonic acids.