Triethyl 2-fluoro-2-phosphonoacetate
Triethyl 2-fluoro-2-phosphonoacetate (CAS: 2356-16-3) is a fluorinated phosphonate ester with a molecular weight of 242.18. This versatile reagent, often employed in organic synthesis, is a key component in C-C bond formation and olefination reactions. Its applications extend to the stereoselective synthesis of unsaturated esters and fluorides, making it valuable in the preparation of complex molecules.
- IUPAC
- 2-Fluoro-2-phosphonoacetic acid triethyl ester,Diethyl [(ethoxycarbonyl)fluoromethyl]phosphonate,Ethyl diethylphosphonofluoroacetate
- Synonyms
- 2-Fluoro-2-phosphonoacetic acid triethyl esterDiethyl [(ethoxycarbonyl)fluoromethyl]phosphonateEthyl diethylphosphonofluoroacetate
Horner-Wadsworth-Emmons Reagent
Utilised in the stereoselective synthesis of unsaturated esters, fluorides, and nitriles through reactions with aldehydes and ketones. This method is a cornerstone for creating specific alkene geometries.
Diels-Alder Reactions
Serves as a reactant in Diels-Alder cycloaddition reactions, facilitating the formation of cyclic compounds with controlled stereochemistry.
Fluorinated Compound Synthesis
Enables the introduction of fluorine into organic molecules, a critical step in the development of pharmaceuticals and agrochemicals due to fluorine's impact on metabolic stability and binding affinity.
Click Chemistry Precursor
Can be employed in addition reactions that subsequently find application in click chemistry, allowing for efficient and reliable bioconjugation and material science modifications.
| Molecular weight | 242.18 |
|---|---|
| Linear formula | (C2H5O)2P(O)CH(F)CO2C2H5 |
| Assay | 96% |
| Boiling point | 75 °C/0.01 mmHg(lit.) |
| Density | 1.194 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.425(lit.) |
| Application | Reactant for: • Diels-Alder reactions1• Biosynthesis of terpene2• Stereoselective synthesis of unsaturated esters, fluorides and nitriles from the reactions of aldehydes and ketones using Wadsworth-Emmons phosphonates3• Synthesis of quinolones4• Horner-Wadsworth-Emmons asymmetric hydration5• Addition reactions and the subsequent application to click chemistry6• Asymmetric intermolecular Stetter reactions7 |
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 | 73 °C / 163.4 °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 Triethyl 2-fluoro-2-phosphonoacetate used for?
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Triethyl 2-fluoro-2-phosphonoacetate is primarily used as a reactant in organic synthesis, particularly for C-C bond formation, olefination reactions (e.g., Horner-Wadsworth-Emmons reactions), Diels-Alder reactions, and the stereoselective synthesis of fluorinated compounds.
What is the CAS number and chemical formula for Triethyl 2-fluoro-2-phosphonoacetate?
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The CAS number is 2356-16-3, and the linear formula is (C2H5O)2P(O)CH(F)CO2C2H5.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Triethyl 2-fluoro-2-phosphonoacetate with an assay of 96%. This product is intended for research and synthesis purposes and is not supplied as USP, BP, EP, or any pharmacopoeia grade.
How should Triethyl 2-fluoro-2-phosphonoacetate be handled?
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Handle Triethyl 2-fluoro-2-phosphonoacetate with appropriate personal protective equipment. It is classified as a warning substance (GHS07) and can cause skin irritation (H315), serious eye irritation (H319), and respiratory irritation (H335). Use safety glasses, chemical-resistant gloves, and ensure adequate ventilation or use a suitable respirator. Refer to the Safety Data Sheet for comprehensive guidance.
Can I request a quote or sample for Triethyl 2-fluoro-2-phosphonoacetate?
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Yes, you can request a quote or sample for Triethyl 2-fluoro-2-phosphonoacetate by contacting our sales team through the website or by phone.
Is Triethyl 2-fluoro-2-phosphonoacetate exported by TSS?
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Yes, Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals, including Triethyl 2-fluoro-2-phosphonoacetate.
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