683-08-9

Usage

Uses

Used in Pharmaceutical Industry:
Diethyl methylphosphonate is used as a precursor for the synthesis of gem-difluoroalkenyphosphonate via reaction with alpha-trifluoromethylstyrene. Diethyl methylphosphonate has potential applications in the development of pharmaceuticals.
Used in Peptide Synthesis:
Diethyl methylphosphonate is used as a building block in the synthesis of phosphonylated peptides, which have potential applications in medicinal chemistry and drug discovery.
Used in Fluoroalkyl Aminophosphonate Synthesis:
Diethyl methylphosphonate is used as a starting material for the synthesis of fluoroalkyl alphaand beta-aminophosphonates, which are of interest in the development of new pharmaceutical agents.
Used in Pyridone Alkaloid Synthesis:
Diethyl methylphosphonate is used in the synthesis of pyridone alkaloids with neuritogenic activity, which may have potential applications in the treatment of neurological disorders.
Used in Prodrug Development:
Diethyl methylphosphonate is used in the synthesis of lipophilic meropenem-derived prodrugs, which can improve the pharmacokinetic properties and bioavailability of the parent drug.
Used in Environmental Applications:
Diethyl methylphosphonate is readily mineralized by photoexcited titanium dioxide (TiO2), making it suitable for use in environmental remediation processes.

InChI:InChI=1/C5H13O3P/c1-3-5(4-2)9(6,7)8/h5H,3-4H2,1-2H3,(H2,6,7,8)/p-2

Upstream product

• 20502-41-4 diethyl methyl phosphite 
• 74-88-4 methyl iodide 
• 80-40-0 ethyl ester of p-toluenesulfonic acid 
• 756-79-6 dimethyl methane phosphonate 
• 27795-39-7 1,2,5-trimethyl-Δ³-phospholene 
• 51207-25-1 ethylphenylsulfoxide 
• 64-17-5 ethanol 
• 6395-57-9 O,O-di-4-nitrophenyl methylphosphonate 
• 1832-53-7 ethyl methylphosphonic acid 
• 41760-84-3 diethyl methoxycarbonylphosphonate 
• 6838-91-1 sodium O-ethyl methylphosphonate 
• 51865-09-9 (S)-(-)-O-ethyl S-methyl methylphosphonothioate 
• 142088-09-3 sodium salt of (+)-pinacolyl alcohol 
• 57578-88-8 (R)-(+)-O-ethyl S-methyl methylphosphonothioate 

Downstream Products

• 35189-94-7 (2-Hydroxy-2,2-diphenyl-ethyl)-phosphonic acid diethyl ester 
• 59870-82-5 oxo-2 phenyl-4 butenyl-3,4 phosphonate de diethyle 
• 1122-55-0 (dichloromethylene)cyclohexane 
• 13736-61-3 (2E)-1-(4-chlorophenyl)-3-(4-nitrophenyl)prop-2-en-1-one 
• 3347-21-5 S-ethyl O,O-dimethyl phosphorodithioate 
• 18000-58-3 bis(cyclohexylammonium) methylphosphonate 
• 698-88-4 (2,2-dichlorovinyl)benzene 
• 25362-01-0 (Z)-diethyl styrylphosphonate 
• 20408-33-7 diethyl (E)-(2-phenylethenyl)phosphonate 
• 64577-15-7 N,N-tetramethyl phenyl-2 ethenyl-1,2 phosphonate 
• 4192-77-2 ethyl cinnamate 
• 795-47-1 (E)-diphenyl(styryl)phosphine oxide 
• 3699-83-0 phenylcarbamoylmethylphosphonic acid diethyl ester 
• 125506-59-4 (Bis-phenylcarbamoyl-methyl)-phosphonic acid diethyl ester 

Relevant academic research and scientific papers

Synthesis of 2-(Thiophen-3-yl)vinylphosphonic acid

A simple and efficient synthesis of 2-(thiophen-3-yl)vinylphosphonic acid has been developed. The title compound is obtained in 70% yield by addition of thiophene-3-carbaldehyde to lithium diethyl methylenephosphonate, followed by dehydration and hydrolysis. 1H, 13C, and 31P NMR spectra are presented for each of the intermediates. Copyright Taylor & Francis Group, LLC.

Intramolecular O → Si donor-acceptor interaction in R 2P(=O)CH2CH2SiF3 molecules: Synthesis of dialkyl [2-(trifluorosilyl)ethyl]phosphonate and bis[(chloromethyl)dimethylsilyl] styrylphosphonate

The reaction of diethyl [2-(triethoxysilyl)ethyl]phosphonate with boron trifluoride etherate was used to synthesize diethyl [2-(trifluorosilyl)ethyl] phosphonate. The reaction of bis(trimethylsilyl) styrylphosphonate with chloro(chloromethyl)dimethylsilane gave bis[(chloromethyl)dimethylsilyl] styrylphosphonate. Multinuclear 1H, 13C, 19F, 29Si, and 31P NMR spectroscopy established the absence of a P=O → Si coordination bond in these compounds and the four-coordinate state of the silicon atom. Evidence for this finding was obtained by B3LYP/6-31G(d) quantum-chemical calculations. However, the same calculations for R2P(=O)? CH2CH2SiF3 (R = Me, Me2N) showed the presence in such molecules of an O → Si coordination bond both in the gas phase and in CHCl3 solution. The distance between the O and Si atoms in this series molecules decreases with R in the order: MeO > Me > Me2N. The axial Si-F bond length increases in the same order and parallels the order of the Hammet σ 0 m constants of these substituents, relating to their interaction with π-electron systems. Nauka/Interperiodica 2006.

Microwave-assisted ionic liquid-catalyzed selective monoesterification of alkylphosphonic acids—an experimental and a theoretical study

It is well-known that the P-acids including phosphonic acids resist undergoing direct es-terification. However, it was found that a series of alkylphoshonic acids could be involved in mo-noesterification with C2–C4 alcohols under microwave (MW) irradiation in the presence of [bmim][BF4] as an additive. The selectivity amounted to 80–98%, while the isolated yields fell in the range of 61–79%. The method developed is a green method for P-acid esterification. DFT calculations at the M062X/6–311+G (d,p) level of theory (performed considering the solvent effect of the corresponding alcohol) explored the three-step mechanism, and justified a higher enthalpy of activation (160.6–194.1 kJ·mol–1) that may be overcome only by MW irradiation. The major role of the [bmim][BF4] additive is to increase the absorption of MW energy. The specific chemical role of the [BF4] anion of the ionic liquid in an alternative mechanism was also raised by the computations.

Access to chiral α-substituted-β-hydroxy arylphosphonates enabled by biocatalytic dynamic reductive kinetic resolution

Ketoreductase (KRED)-catalyzed dynamic reductive kinetic resolution (DYRKR) of α-substituted-β-keto arylphosphonates was developed as a generic and stereoselective approach to synthesize chiral α-substituted-β-hydroxy arylphosphonates, with moderate-to-excellent isolated yield (up to 96%), good-to-excellent diastereoselectivity (up to >99 : 99% ee) being achieved.

Solvent-Free Michaelis-Arbuzov Rearrangement under Flow Conditions

The first solvent- and catalyst-free procedure for the Michaelis-Arbuzov reaction under flow conditions was developed. A variety of alkylphosphonic esters could be obtained using this protocol starting from the corresponding trialkyl phosphites and even catalytic amounts of alkyl halides with very short reaction times (8.33-50 min) and excellent conversions. In general, this protocol works effectively when the alkyl halide is used in catalytic amounts as low as 5-10% only if it concerns the synthesis of homo alkylphosphonates. One equivalent and an excess of alkyl halides should be used in the reaction with alkyl phosphite if the alkyl group of the selected substrates differ. Thus, it provides a sustainable, fast alternative to the existing methods for the preparation of alkylphosphonates. The isolation of the reaction products is straightforward due to the lack of solvents and a high purity of the obtained products (conv ≥ 99%), and notably, in the catalytic procedures there are only traces of alkyl halides formed after the reaction is complete. The reactions conducted using a glass microreactor chip with an internal volume of 250 μL allow the production of 1.6-1.95 g of organophosphorus esters per hour.

Discovery of phosphonamidate IDO1 inhibitors for the treatment of non-small cell lung cancer

Targeting indoleamine 2,3-dioxygenase 1 (IDO1) has been identified as an attractive approach for the development of cancer immunotherapy. In this study, a series of phosphonamidate ester containing compounds were designed, synthesized and evaluated for their inhibitory activities against IDO1. Among them, compounds 16, 17, and 26 with good IDO1 inhibitory (HeLa IDO1 IC50 = 10–21 nM, hIDO1 IC50 = 78–121 nM) activities were selected for further investigation and showed good physicochemical properties. Furthermore, based on comparable PK profile and excellent IDO2/TDO inhibitory potency, representative compound 16 was selected for further bio-evaluation and characterized with good efficacy in suppressing lung metastasis (77% inhibition rate) of Lewis cells in vivo. Thus, compound 16 could be a potential and efficacious agent for further evaluation.

Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates

A strategy for the direct functionalization strategy of inertial dialkyl phosphonates with hydroxy compounds to afford diverse mixed phosphonates with good yields and functional-group tolerance has been developed. Mechanistic investigations involving both NMR studies and DFT studies suggest that an unprecedented highly reactive PV species (phosphoryl pyridin-1-ium salt), a key intermediate for this new synthetic transformation, is generated in situ from dialkyl phosphonate in the presence of Tf2O/pyridine.

Synthesis method of glufosinate ammonium intermediate alkyl phosphodiester compound

The invention discloses a synthesis method of a glufosinate ammonium intermediate alkyl phosphodiester compound. According to the method, phosphite trimester and halogenated hydrocarbon or alcohol or phenol are subjected to substitution reaction so as to obtain the glufosinate ammonium intermediate alkyl phosphodiester. The method takes phosphite trimester as the raw material to carry out substitution reaction with halogenated hydrocarbon or alcohol or phenol at certain temperature to obtain the corresponding product alkyl phosphodiester, and the product can be further prepared into glufosinate ammonium. The method changes the existing process of using methyl diethyl phosphite to prepare glufosinate ammonium, has the characteristics of low production cost, safety and environmental protection, and at the same time avoids the risk in the process of industrialization.

PHOTOLABILE PRO-FRAGRANCES

The present invention relates to a method for producing photocleavable scent precursors, to products containing the scent precursors, and to the use of the scent precursors for prolonging the scent impression in the product and on surfaces treated with the product.

PHOTOLABILE PRO-FRAGRANCES

The present invention relates to a method for producing photocleavable scent precursors, to products containing the scent precursors, and to the use of the scent precursors for prolonging the scent impression in the product and on surfaces treated with the product.