Ethyl dimethylphosphonoacetate
Ethyl dimethylphosphonoacetate (CAS: 311-46-6) is an organophosphorus compound with the linear formula (CH3O)2P(O)CH2COOC2H5 and a molecular weight of 196.14 g/mol. As a key reagent in synthetic organic chemistry, it is primarily utilised for C-C bond formation, particularly in Horner-Wadsworth-Emmons reactions to produce various organic molecules.
- IUPAC
- Ethoxycarbonylmethylphosphonic acid dimethylester,Phosphonoacetic acid P,P-dimethyl ethylester
- Synonyms
- Ethoxycarbonylmethylphosphonic acid dimethylesterPhosphonoacetic acid P,P-dimethyl ethyl ester
Horner-Wadsworth-Emmons Reactions
This reagent serves as a vital component in Horner-Wadsworth-Emmons reactions, enabling the synthesis of alkenylcarboxylates. This application is fundamental in constructing carbon-carbon double bonds with controlled stereochemistry.
Synthesis of Pharmaceutical Intermediates
Ethyl dimethylphosphonoacetate is employed in the synthesis of complex molecules, including non-nucleoside inhibitors of HCV polymerase NS5B and Neuropeptide Y1 receptor antagonists, highlighting its role in medicinal chemistry research and development.
Enantioselective Transfer Hydrogenation
It acts as a reactant in enantioselective transfer hydrogenation processes, crucial for the preparation of specific chiral fragments, such as the C7-C14 segment of ulapualide A.
Olefination Reactions
The compound is used in the olefination of peptidyl aldehydes with stabilised ylides, a method for introducing alkene functionalities into peptide-based structures.
| Molecular weight | 196.14 |
|---|---|
| Linear formula | (CH3O)2P(O)CH2COOC2H5 |
| Assay | ≥90% (GC) |
| Boiling point | 134 °C/10 mmHg(lit.) |
| Density | 1.188 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.435(lit.)n20/D 1.435 |
| Application | Reactant for synthesis of: • Non-nucleoside inhibitors of HCV polymerase NS5B1• Neuropeptide Y1 receptor antagonists2• Alkenylcarboxylates from Horner-Wadsworth-Emmons reactions3Reactant for: • Enantioselective transfer hydrogenation for preparation of the C7-C14 fragment of ulapualide A4 • Intramolecular Michael reactions5• Olefination of peptidyl aldehydes with stabilized ylides6 |
| Protective equipment | Eyeshields, Gloves |
|---|---|
| Flash point | 99 °C / 210.2 °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 Ethyl dimethylphosphonoacetate used for?
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Ethyl dimethylphosphonoacetate is used as a reactant for C-C bond formation, particularly in Horner-Wadsworth-Emmons reactions for synthesising alkenylcarboxylates, and in the preparation of pharmaceutical intermediates and other complex organic molecules.
What are the CAS number and formula for Ethyl dimethylphosphonoacetate?
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The CAS number for Ethyl dimethylphosphonoacetate is 311-46-6, and its linear formula is (CH3O)2P(O)CH2COOC2H5.
What grade and purity does Tech Serve Solutions supply for Ethyl dimethylphosphonoacetate?
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Tech Serve Solutions supplies Ethyl dimethylphosphonoacetate with an assay of ≥90% (GC). TSS does not represent this product as USP/BP/EP or any other pharmacopoeial grade.
How should Ethyl dimethylphosphonoacetate be handled safely?
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Ethyl dimethylphosphonoacetate has a flash point of 99 °C (210.2 °F) and is classified under WGK Germany 3. Appropriate personal protective equipment, including eyeshields and gloves, should be worn during handling.
Can Ethyl dimethylphosphonoacetate be shipped internationally?
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Yes, Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals, including Ethyl dimethylphosphonoacetate, and can facilitate international shipments.
How can I request a sample or quote for Ethyl dimethylphosphonoacetate?
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To request a sample or a quote for Ethyl dimethylphosphonoacetate, please contact our sales team via the website or your dedicated account manager.
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