Diethylphosphonoacetic acid
Diethylphosphonoacetic acid (CAS: 3095-95-2) is an organophosphorus compound with the linear formula (C2H5O)2P(O)CH2CO2H and a molecular weight of 196.14. This chemical serves as a valuable reagent in synthetic organic chemistry, particularly in C-C bond formation. It acts as a nucleophile in addition reactions and is a key reactant in various named reactions, including Horner-Wadsworth-Emmons olefination and Ugi-Dieckmann reactions, facilitating the synthesis of complex organic molecules.
- IUPAC
- (Diethoxyphosphinyl)acetic acid,Diethyl carboxymethylphosphonate,NSC 272281
- Synonyms
- (Diethoxyphosphinyl)acetic acidDiethyl carboxymethylphosphonateNSC 272281
Nucleophilic Addition Reactions
Diethylphosphonoacetic acid functions as a nucleophile in addition reactions, enabling the synthesis of compounds such as allene epoxides. Its reactivity is well-suited for constructing carbon-carbon bonds in various synthetic pathways.
Horner-Wadsworth-Emmons Reagent
This compound is employed in Horner-Wadsworth-Emmons reactions, a crucial method for the stereoselective synthesis of alkenes. It facilitates the formation of carbon-carbon double bonds from carbonyl compounds.
Stereoselective Synthesis Studies
It is utilized as a reactant in stereoselectivity studies, including the Staudinger reaction and the enantioselective formation of diols via epoxidation and hydration. These applications highlight its role in precise molecular construction.
Ireland-Claisen Rearrangement
Diethylphosphonoacetic acid participates in the remote chelation-controlled Ireland-Claisen rearrangement, a powerful tool for carbon skeleton rearrangement and the synthesis of functionalized carboxylic acid derivatives.
Ugi-Dieckmann Reactions
The compound is a reactant in Ugi-Dieckmann reactions, which are used for the synthesis of tetramic acid derivatives. This application demonstrates its utility in constructing heterocyclic systems.
| Molecular weight | 196.14 |
|---|---|
| Linear formula | (C2H5O)2P(O)CH2CO2H |
| Assay | 95% |
| Boiling point | 150 °C/0.05 mmHg(lit.) |
| Density | 1.220 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.445(lit.) |
| Application | Acts as a nucleophile for nucleophilic addition reactions for synthesis of allene epoxides1Reactant for: • Stereoselectivity studies of the Staudinger reaction2• Enantioselective formation of diols via epoxidation and hydration reactions3• Horner-Wadsworth-Emmons reactions4,5• Remote chelation controlled Ireland-Claisen rearrangement6• Ugi-Dieckmann reactions for synthesis of tetramic acid derivatives7 |
Hazard statements
- H302Harmful if swallowed
| Protective equipment | Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
|---|---|
| Flash point | >110 °C / >230 °F |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xn |
| Risk statements (R) | 22 |
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 Diethylphosphonoacetic acid used for?
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Diethylphosphonoacetic acid is used as a nucleophile in addition reactions for the synthesis of allene epoxides and as a reactant in stereoselectivity studies of the Staudinger reaction, enantioselective formation of diols, Horner-Wadsworth-Emmons reactions, Ireland-Claisen rearrangement, and Ugi-Dieckmann reactions for tetramic acid derivative synthesis.
What is the CAS number and chemical formula for Diethylphosphonoacetic acid?
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The CAS number for Diethylphosphonoacetic acid is 3095-95-2, and its linear formula is (C2H5O)2P(O)CH2CO2H.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Diethylphosphonoacetic acid with an assay of 95%. TSS does not represent this product as USP, BP, or EP grade.
How should Diethylphosphonoacetic acid be handled safely?
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Diethylphosphonoacetic acid is harmful if swallowed (H302). Appropriate personal protective equipment includes eyeshields, face shields, and gloves. A full-face respirator or a multi-purpose combination respirator cartridge is recommended.
How is Diethylphosphonoacetic acid packed, shipped, and exported?
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Diethylphosphonoacetic acid is carefully packed for shipment and exported globally by Tech Serve Solutions, adhering to all relevant transportation and chemical handling regulations.
How can I request a sample or quote for Diethylphosphonoacetic acid?
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To request a sample or a quote for Diethylphosphonoacetic acid, please contact our sales team through the website or by phone.
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