Allyl P,P-diethylphosphonoacetate
Allyl P,P-diethylphosphonoacetate (CAS 113187-28-3), with the molecular formula (C2H5O)2P(O)CH2COOCH2CH=CH2 and a molecular weight of 236.20 g/mol, is a key organic compound. It is widely employed as a reagent in C-C bond formation and chemical synthesis, particularly within the Horner-Wadsworth-Emmons reaction. This phosphonate ester serves as a versatile building block for preparing complex molecules, including functionalised cyclopentenones and biologically active compounds.
- IUPAC
- Phosphonoacetic acid P,P-diethyl allyl ester
- Synonyms
- (C2H5O)2P(O)CH2COOCH2CH=CH2Phosphonoacetic acid P,P-diethyl allyl ester
Horner-Wadsworth-Emmons Reactions
This compound is a valuable reactant for performing Horner-Wadsworth-Emmons reactions, a widely used olefination method for forming carbon-carbon double bonds.
Preparation of Phosphonate-Functionalized Cyclopentenones
It serves as a precursor in the regioselective Pauson-Khand reactions for the synthesis of phosphonate-functionalized cyclopentenones.
Synthesis of Anticancer Agents
Used in the preparation of salicylihalamide analogs, such as saliphenylhalamide, investigated for their potential as vacuolar ATPase inhibitors and anticancer agents.
Solid-Phase Peptide Synthesis
Applied in the solid-phase synthesis of olefin-containing peptides, specifically as inhibitors of HTLV-1 protease, utilising the Horner-Emmons reaction.
Dendrimer Synthesis
Incorporated into the synthesis of fluorescent poly(aromatic amide) dendrimers, contributing to the development of advanced macromolecular structures.
| Molecular weight | 236.20 |
|---|---|
| Linear formula | (C2H5O)2P(O)CH2COOCH2CH=CH2 |
| Assay | 97% |
| Boiling point | 157-158 °C/10 mmHg(lit.) |
| Density | 1.12 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.445(lit.) |
| Application | Reactant for:• Horner-Wadsworth-Emmons reaction1• Preparation of phosphonate-functionalized cyclopentenones via regioselective Pauson-Khand processes2• Preparation of salicylihalamide analog saliphenylhalamide as potential vacuolar ATPase inhibitors and anticancer agents3• Solid-phase synthesis of olefin-containing peptides via Horner-Emmons reaction as inhibitors of HTLV-1 protease4• Synthesis of fluorescent poly(aromatic amide) dendrimers5 |
Hazard statements
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P305IF IN EYES
| Protective equipment | Eyeshields, 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) | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36 |
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 Allyl P,P-diethylphosphonoacetate used for?
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Allyl P,P-diethylphosphonoacetate (CAS 113187-28-3) is primarily used as a reagent in chemical synthesis, notably for C-C bond formation via the Horner-Wadsworth-Emmons reaction. It is also employed in the preparation of phosphonate-functionalised cyclopentenones, potential anticancer agents, olefin-containing peptides, and fluorescent dendrimers.
What is the CAS number and formula for Allyl P,P-diethylphosphonoacetate?
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The CAS number for Allyl P,P-diethylphosphonoacetate is 113187-28-3. Its linear formula is (C2H5O)2P(O)CH2COOCH2CH=CH2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Allyl P,P-diethylphosphonoacetate with an assay of 97%. This product is supplied for research and laboratory use. TSS does not represent this product as USP, BP, EP, or any other pharmacopoeia grade.
What are the safety and handling precautions for this chemical?
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Allyl P,P-diethylphosphonoacetate is classified with a Warning signal word, with hazard statements H315 (Causes skin irritation), H319 (Causes serious eye irritation), and H335 (May cause respiratory irritation). Appropriate personal protective equipment, including eyeshields and gloves, should be worn. Use in a well-ventilated area or with appropriate respiratory protection. P261, P305, P351, and P338 are precautionary statements.
How is Allyl P,P-diethylphosphonoacetate packaged and shipped?
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Tech Serve Solutions exports chemicals globally. Packaging is performed according to international shipping regulations to ensure safe transit. Please contact us for specific shipping and export details.
How can I request a sample or quote for Allyl P,P-diethylphosphonoacetate?
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To request a sample or a quotation for Allyl P,P-diethylphosphonoacetate, please navigate to the product page and utilise the 'Request Sample' or 'Request Quote' buttons. Alternatively, you may contact our sales team directly.
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