54553-21-8

Usage

Uses

Used in Chemical Synthesis:
DIETHYL 2-PHENYLETHYL PHOSPHONATE 98 is used as a reactant for the preparation of 1,3-diketones, β-keto esters, and β-keto phosphonates via 1,2-addition of carbanionic nucleophiles to cyclic vinylogous acyl triflates, followed by ring-opening fragmentation, Claisen condensation, and carbon-carbon bond cleavage.
Used in Nanotechnology:
DIETHYL 2-PHENYLETHYL PHOSPHONATE 98 is used as a reagent for controlling the surface state emission in ultrasmall CdSe nanocrystals, which can be applied in various optoelectronic devices and solar cells.
Used in Organophosphorous Compounds Synthesis:
DIETHYL 2-PHENYLETHYL PHOSPHONATE 98 is used as a reactant in reactions with organoboranes for the synthesis of organophosphorous compounds, which have a wide range of applications in the pharmaceutical, agrochemical, and materials science industries.

InChI:InChI=1/C12H19O3P/c1-3-14-16(13,15-4-2)11-10-12-8-6-5-7-9-12/h5-9H,3-4,10-11H2,1-2H3

Upstream product

• 103-63-9 1-phenyl-2-bromoethane 
• 122-52-1 triethyl phosphite 
• 64-17-5 ethanol 
• 100-41-4 ethylbenzene 
• 20408-33-7 diethyl (E)-(2-phenylethenyl)phosphonate 
• 591-50-4 iodobenzene 
• 682-30-4 Diethyl vinylphosphonate 
• 100-42-5 styrene 
• 762-04-9 phosphonic acid diethyl ester 
• 36525-03-8 trans-2-Phenylethenylmercuric chloride 
• 92167-80-1 O,O-diethyl chloro-1 phenyl-2 ethenyl-1,2 phosphonate 
• 100-58-3 phenylmagnesium bromide 
• 1018-24-2 diethyl styrylphosphonate 
• 683-08-9 Diethyl methylphosphonate 

Downstream Products

• 85093-26-1 diethyl (1-benzylbut-3-enyl)phosphonate 
• 88501-39-7 C₁₀H₁₄ClO₂P 
• 14295-50-2 phenethyl-phosphonic acid monoethyl ester 
• 4672-30-4 (2-phenylethyl)phosphonic acid 
• 100525-35-7 (4-amino-phenethyl)-phosphonic acid diethyl ester 
• 106037-34-7 (4-nitro-phenethyl)-phosphonic acid 
• 253345-84-5 (1-benzyl-2-oxiranyl-ethyl)-phosphonic acid diethyl ester 
• 140157-17-1 (2-Benzyl-3,3-diphenyl-oxiranyl)-phosphonic acid diethyl ester 

Relevant academic research and scientific papers

Intensified Continuous Flow Michaelis-Arbuzov Rearrangement toward Alkyl Phosphonates

Herein is described the development of an intensified continuous flow process for the preparation of a library of alkyl phosphonates through a Michaelis-Arbuzov rearrangement. A careful process optimization and thorough analysis of the competitive reactions led to a very attractive protocol with unprecedented productivities (up to 4.97 kg of material per day) and a low environmental footprint with the absence of solvent, additives, catalysts, and waste. In-line low-field 31P NMR monitoring was conveniently implemented for rapid optimization and process monitoring. Two key alkyl phosphonate intermediates were also assessed for the unprecedented diazene dicarboxylate-mediated electrophilic amination under continuous flow conditions toward the α-aminophosphonic acid derivatives of Pphenylalanine and Palanine, bioisosters of the natural amino acids phenylalanine and alanine, respectively.

Nickel-catalyzed coupling of R2P(O)Me (R = aryl or alkoxy) with (hetero)arylmethyl alcohols

α-Alkylation of methyldiarylphosphine oxides with (hetero)arylmethyl alcohols was performed under nickel catalysis. Various arylmethyl and heteroarylmethyl alcohols can be used in this transformation. A series of methyldiarylphosphine oxides were alkylated with 30-90% yields. Functional groups on the aromatic rings of methyldiarylphosphine oxides or arylmethyl alcohols including OMe, NMe2, SMe, CF3, Cl, and F groups can be tolerated. The conditions are also suitable for the α-alkylation reaction of dialkyl methylphosphonates.

SAR of non-hydrolysable analogs of pyridoxal 5′-phosphate against low molecular weight protein tyrosine phosphatase isoforms

Kinases and phosphatases are key enzymes in cell signal transduction pathways. Imbalances in these enzymes have been linked to numerous disease states ranging from cancer to diabetes to autoimmune disorders. The two isoforms (IFA and IFB) of Low Molecular Weight Protein Tyrosine Phosphatase (LMW-PTP) appear to play a role in these diseases. Pyridoxal 5′-phosphate (PLP) has been shown to act as a potent but, impractical micromolar inhibitor for both isoforms. In this study, a series of non-hydrolysable phosphonate analogs of PLP were designed, synthesized and tested against the two isoforms of LMW-PTP. Assay results demonstrated that the best inhibitor for both isoforms was compound 5 with a Kis of 1.84 μM (IFA) and 15.6 μM (IFB). The most selective inhibitor was compound 16, with a selectivity of roughly 370-fold for IFA over IFB.

Bismuth(III)-Catalyzed Sequential Enamine-Imine Tautomerism/2-Aza-Cope Rearrangement of Stable β-Enaminophosphonates: One-Pot Synthesis of β-Aminophosphonates

A novel catalytic tautomeric transformation of a β-enaminophosphoryl and 2-aza-Cope rearrangement sequence has been successfully applied to the one-pot synthesis of β-aminophosphonates with high efficiency and good tolerance. In this tandem reaction, Bi(OTf)3 exhibits unique activities and promotes both of enamine-imine tautomerism and 2-aza-Cope rearrangement.

Chemoselective Activation of Diethyl Phosphonates: Modular Synthesis of Biologically Relevant Phosphonylated Scaffolds

Phosphonates have garnered considerable attention for years owing to both their singular biological properties and their synthetic potential. State-of-the-art methods for the preparation of mixed phosphonates, phosphonamidates, phosphonothioates, and phos

Efficient synthesis of α-substituted ethylphosphonates via CuH-catalyzed conjugate reduction of terminal alkenylphosphonate

An unprecedented approach toward synthesis of α-substituted ethylphosphonates based on CuH-catalyzed conjugate reduction of vinylphosphonates has been successfully developed. This protocol features mild conditions, broad substrate scope, good functional group compatibility, high overall efficiencies, and easy gram-scale synthesis. The Cu-catalyzed reduction takes place in a highly selective manner on the phosphono substituted C[dbnd]C bond in the case of the reaction of alkenylphosphonates bearing both phosphono and alkyl or aryl substituted alkene moieties. Furthermore, the result of competitive reaction indicates that the Cu-catalyzed conjugate reduction of vinylphosphonate is more challenging and reproducible than the corresponding acrylate's reaction.

A new approach towards synthesis of phosphorylated alkenes

New method of synthesis of trans-vinylphosphonates via reaction of trimethylsilyl(methyl)phosphonites with carbonyl compounds in the presence of carbon tetrachloride has been developed. The reaction involves formation of C-trimethylsilyl substituted ylide

Palladium-catalyzed hydrophosphonylation of alkenes with dialkyl H-phosphonates

The palladium-catalyzed hydrophosphonylation of alkenes with previously unreactive acyclic dialkyl H-phosphonates has been developed. A catalyst system based on palladium/DavePhos or palladium/SPhos enables the transformation of various alkenes to phospho

In situ generation of phosphoryl alkylindiums and their synthetic application to arylalkyl phosphonates via palladium-catalyzed cross-coupling reactions

Phosphoryl alkylindium reagents are generated in situ from the direct insertion of indium with bromoalkyl phosphonates in the presence of CuCl, and their synthetic application to arylalkyl phosphonates is reported via a Pd-catalyzed cross-coupling reactio

Copper-catalyzed synthesis of alkylphosphonates from H-phosphonates and N-tosylhydrazones

A new catalytic system for the alkylation of H-phosphonates and diphenylphosphine oxide with N-tosylhydrazones has been developed. In the presence of copper(I) iodide and base, H-phosphonates react with N-tosylhydrazones to afford the corresponding coupled alkylphosphonates in good to excellent yields without any ligands. Alkylphosphonates can also be prepared in a one-pot process directly from carbonyl compounds without the isolation of tosylhydrazone intermediates.