20408-33-7

Basic information

• Product Name: Phosphonic acid, [(1E)-2-phenylethenyl]-, diethyl ester
• CAS NO: 20408-33-7
• Molecular Formula: C12H17O3P
• Molecular Weight: 240.239
• Mol File: 20408-33-7.mol
• Article Data: 85

Chemical Properties

• CAS DataBase Reference: Phosphonic acid, [(1E)-2-phenylethenyl]-, diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonic acid, [(1E)-2-phenylethenyl]-, diethyl ester(20408-33-7)
• EPA Substance Registry System: Phosphonic acid, [(1E)-2-phenylethenyl]-, diethyl ester(20408-33-7)

Safety Data

• Hazardous Substances Data: 20408-33-7(Hazardous Substances Data)

Upstream product

• 116800-91-0 C₉H₂₁O₆P₂^(1-) 
• 100-52-7 benzaldehyde 
• 762-04-9 Diethyl phosphonate 
• 33142-26-6 Diethyl (1-Formyl-1-phenylmethyl)phosphonate 
• 103-64-0 bromostyrene 
• 122-52-1 triethyl phosphite 
• 259677-37-7 diethyl Z-2-butyltelluro-2-phenylethenylphosphonate 
• 259677-34-4 (Z)-1-(diethoxyphosphonyl)-2-(phenyltelluryl)-2-phenylethene 
• 100-44-7 benzyl chloride 
• 7436-90-0 2,2-dibromostyrene 
• 762-04-9 phosphonic acid diethyl ester 
• 102-96-5 (2-nitroethenyl)benzene 
• 72019-14-8 (2-hydroxy-2-phenyl-ethyl)-phosphonic acid diethyl ester 
• 591-50-4 iodobenzene 

Downstream Products

• 261167-62-8 (2S,5R,1'R)-2-[2'-(diethoxyphosphoryl)-1'-phenylethyl]-3,6-diethoxy-2,5-dihydro-5-isopropyl-2-methylpyrazine 
• 261167-63-9 (2S,5R,1'S)-2-[2'-(diethoxyphosphoryl)-1'-phenylethyl]-3,6-diethoxy-2,5-dihydro-5-isopropyl-2-methylpyrazine 
• 6324-00-1 1-amino-2-phenylethanephosphonic acid 
• 60096-50-6 (S)-N-Nitroso-O-methylprolinol 
• 618892-50-5 (2R,5S,1'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine 
• 182207-34-7 (2R,5S,1'S)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine 
• 164358-33-2 diethyl (1S,2S)-1,2-dihydroxy-2-phenylethylphosphonate 
• 173657-53-9 diethyl (1R,2R)-1,2-dihydroxy-2-phenylethylphosphonate 
• 97006-83-2 (1,2-Dihydroxy-2-phenyl-ethyl)-phosphonic acid diethyl ester 

Relevant articles and documents

Mechanistic insight into the copper-catalyzed phosphorylation of terminal alkynes: A combined theoretical and experimental study

The reaction mechanism of copper-catalyzed phosphorylation of terminal alkynes under different conditions has been investigated experimentally and theoretically. The important role of dioxygen has been elucidated, including the formation of η1-superoxocopper(II), η2- superoxocopper(III), μ-η2:η2-peroxodicopper(II) , and bis(μ-oxo)dicopper(III) complexes. More importantly, the proton transfer from the dialkyl phosphonate (in the form of phosphite) to the bridging oxygen atom entails the migration of the deprotonated phosphonate to the terminal alkyne, leading to the formation of a C-P bond with an activation barrier of only 1.8 kcal/mol. In addition, a particularly stable six-centered dicopper(I) species is formed with the migration of both of the Ph 2P(O) groups from the copper atoms to the oxygen atoms of the bis(μ-oxo) bridge, explaining the experimental observation that secondary phosphine oxides can be oxidized to the phosphinic acids. Thus, the diphenylphosphine oxide was added to the reaction mixture dropwise to minimize the concentration during the reaction course. Gratifyingly, the coupling product was generated almost quantitatively when the reaction was completed.

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Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination

Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.

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.

TEMPO and Silver-Mediated Intermolecular Phosphonylation of Alkenes: Stereoselective Synthesis of (E)-Alkenylphosphonates

An efficient method was developed towards the synthesis of alkenylphosphonates from simple olefins and phosphonate diesters. This method was enabled by the use of cheap and commercially available silver salts and TEMPO. This method exhibits of good functional group tolerance, specific (E)-selectivity for all olefins and vinyl selectivity for aliphatic olefins. A radical mechanism was proposed, and TEMPO was involved in the product formation step.