Diethyl (2-oxo-2-phenylethyl)phosphonate
Diethyl (2-oxo-2-phenylethyl)phosphonate (CAS 3453-00-7) is an organophosphorus compound with the linear formula C6H5COCH2P(O)(OC2H5)2 and a molecular weight of 256.23. This reagent is primarily used in organic synthesis for carbon-carbon bond formation, particularly in Horner-Wadsworth-Emmons reactions and olefination processes. Its utility extends to asymmetric Michael additions and cyclocondensation reactions, making it a valuable tool for synthetic chemists.
- IUPAC
- Diethyl benzoylmethylphosphonate,Diethyl phenacylphosphonate,NSC 648426
- Synonyms
- Diethyl benzoylmethylphosphonateDiethyl phenacylphosphonateNSC 648426
Horner-Wadsworth-Emmons Reactions
Diethyl (2-oxo-2-phenylethyl)phosphonate is a key reagent in Horner-Wadsworth-Emmons (HWE) reactions. It facilitates the synthesis of olefins with high stereoselectivity, playing a crucial role in constructing carbon-carbon double bonds in complex organic molecules.
Asymmetric Michael Additions
This phosphonate participates in asymmetric Michael addition reactions, specifically with β-oxo phosphonates and nitro olefins. These reactions are vital for establishing new carbon-carbon bonds with controlled stereochemistry in chiral synthesis.
Cyclocondensation Reactions
The compound is employed in cyclocondensation reactions to generate arylphosphonates. This application is significant for the synthesis of various organophosphorus heterocycles and functionalised aromatic compounds.
Diazo Transfer Reactions
Diethyl (2-oxo-2-phenylethyl)phosphonate can be used in diazo transfer reactions. This process allows for the synthesis of diazo-phosphonyl compounds, which are useful intermediates in further synthetic transformations.
Gem-Chlorofluorination
It is involved in gem-chlorofluorination of keto phosphonates, followed by functionalization of the resulting products. This pathway provides access to valuable gem-chlorofluoro organic compounds.
| Molecular weight | 256.23 |
|---|---|
| Linear formula | C6H5COCH2P(O)(OC2H5)2 |
| Assay | 97% |
| Boiling point | 192-193 °C/11 mmHg(lit.) |
| Density | 1.179 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.513(lit.) |
| Application | Reactant involved in:• Asymmetric Michael addition of β-oxo phosphonates to nitro olefins1• Gem-chlorofluorination of keto phosphonates with subsequent functionalization of the products2• Cyclocondensation reactions to produce arylphosphonates3• Diazo transfer reactions for synthesis of diazo-phosphonyl compounds4• Horner-Wadsworth-Emmons reactions5• Inverse-electron-demand Diels-Alder reactions6 |
| Protective equipment | Eyeshields, Gloves |
|---|---|
| Flash point | >113 °C / >235.4 °F |
| Water hazard class (WGK, DE) | 3 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is Diethyl (2-oxo-2-phenylethyl)phosphonate used for?
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Diethyl (2-oxo-2-phenylethyl)phosphonate is used in organic synthesis for C-C bond formation, including Horner-Wadsworth-Emmons reactions, asymmetric Michael additions, cyclocondensation reactions, diazo transfer reactions, and gem-chlorofluorination.
What is the CAS number and chemical formula for Diethyl (2-oxo-2-phenylethyl)phosphonate?
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The CAS number is 3453-00-7, and the linear formula is C6H5COCH2P(O)(OC2H5)2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Diethyl (2-oxo-2-phenylethyl)phosphonate at a minimum purity of 97%. This product is supplied for research and chemical synthesis purposes and is not represented as USP, BP, EP, or pharmacopoeia grade.
What are the safety considerations for handling Diethyl (2-oxo-2-phenylethyl)phosphonate?
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Appropriate personal protective equipment, including eyeshields and gloves, should be worn. This compound has a flash point above 113 °C (235.4 °F). Consult the Safety Data Sheet (SDS) for comprehensive handling and hazard information. It is classified under WGK Germany 3.
How is this chemical packed and shipped?
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Tech Serve Solutions professionally packs and exports fine chemicals globally, adhering to all relevant shipping regulations to ensure safe and timely delivery.
How can I request a quote or sample for Diethyl (2-oxo-2-phenylethyl)phosphonate?
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Please contact our sales team or use the online enquiry form on our website to request a quote or sample for Diethyl (2-oxo-2-phenylethyl)phosphonate.
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