Diethyl 3-butenylphosphonate
Diethyl 3-butenylphosphonate (CAS: 15916-48-0), with the linear formula CH2=CHCH2CH2PO(OCH2CH3)2 and a molecular weight of 192.19 g/mol, is a versatile synthetic reagent. It functions as a key reactant in C-C bond formation and olefination reactions. Its applications include the synthesis of bicyclic frameworks, antiviral nucleoside phosphonates, antimalarials, and bisphosphonate enynes, demonstrating its utility in complex organic synthesis and medicinal chemistry.
- IUPAC
- P-3-Buten-1-yl-phosphonic acid diethyl ester
- Synonyms
- P-3-Buten-1-yl-phosphonic acid diethyl ester
Synthesis of Bicyclo[3.3.1]alkenone Frameworks
Diethyl 3-butenylphosphonate serves as a reactant in gold-catalyzed Diels-Alder reactions, enabling the formation of complex bicyclo[3.3.1]alkenone framework compounds.
Preparation of Antiviral Nucleoside Phosphonates
This phosphonate is employed in the synthesis of C-5 substituted pyrimidine acyclic nucleoside phosphonates, which are recognised as substrates for human thymidylate kinase, indicating potential antiviral applications.
Antimalarial Drug Precursors
Through halogenation of diethyl 3-butenylphosphonate, intermediates for the synthesis of novel antimalarial compounds can be prepared.
Formation of Bisphosphonate Enynes
The compound is utilised as a reactant in the synthesis of bisphosphonate enynes, expanding the scope of organophosphorus chemistry.
Catalysis and Cyclopropanation
It finds application in reactions such as the remote supramolecular control of catalyst selectivity in alkene hydroformylation and in intermolecular metal-catalyzed carbenoid cyclopropanations.
| Molecular weight | 192.19 |
|---|---|
| Linear formula | CH2=CHCH2CH2PO(OCH2CH3)2 |
| Assay | 95% |
| Boiling point | 55 °C/0.55 mmHg(lit.) |
| Density | 1.005 g/mL at 25 °C(lit.) |
| Application | Reactant for synthesis of:• Bicyclo[3.3.1]alkenone framework compounds by gold-catalyzed Diels-Alder reactions1• Antiviral C-5-substituted pyrimidine acyclic nucleoside phosphonates selected as human thymidylate kinase substrates2• Antimalarials via halogenation of di-Et butenylphosphonate3• Bisphosphonate enynes4Reactant for:• Remote supramolecular control of catalyst selectivity in hydroformlyation of alkenes5• Intermolecular metal-catalyzed carbenoid cyclopropanations6• Chemoenzymatic synthesis of phosphic derivatives of carbohydrates7 |
Hazard statements
- H301Toxic if swallowed
Precautionary statements
- P301IF SWALLOWED
| Protective equipment | Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
|---|---|
| Flash point | 105 °C / 221 °F |
| Transport (UN / ADR) | UN 2810 6.1 / PGIII |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | T |
| Risk statements (R) | 25 |
| Safety statements (S) | 45 |
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 3-butenylphosphonate used for?
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Diethyl 3-butenylphosphonate is used as a reactant in organic synthesis, particularly for C-C bond formation and olefination. Specific applications include the synthesis of bicyclic compounds, antiviral nucleoside phosphonates, antimalarials, and bisphosphonate enynes.
What are the CAS number and chemical formula for Diethyl 3-butenylphosphonate?
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The CAS number for Diethyl 3-butenylphosphonate is 15916-48-0, and its linear formula is CH2=CHCH2CH2PO(OCH2CH3)2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Diethyl 3-butenylphosphonate with an assay of 95%. TSS does not represent this product as USP, BP, EP, or other pharmacopoeial grades unless explicitly stated.
How should Diethyl 3-butenylphosphonate be handled safely?
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Diethyl 3-butenylphosphonate is classified as acutely toxic (GHS06, Danger, H301). Handling requires appropriate personal protective equipment, including eyeshields, faceshields, gloves, and respiratory protection (e.g., full-face respirator or ABEK filter). Follow all precautionary statements (P301 + P310).
Is Diethyl 3-butenylphosphonate suitable for export?
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Yes, Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals, including Diethyl 3-butenylphosphonate, adhering to all necessary shipping regulations (UN 2810 6.1 / PGIII).
How can I request a quote or sample?
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To request a quote or sample for Diethyl 3-butenylphosphonate, please contact our sales team through the website or by phone, providing your specific requirements.
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