Triethyl 2-chloro-2-phosphonoacetate
Triethyl 2-chloro-2-phosphonoacetate (CAS: 7071-12-7) is a key organophosphorus reagent with the molecular formula (C2H5O)2P(O)CH(Cl)CO2C2H5 and a molecular weight of 258.64 g/mol. This compound serves as a versatile building block in organic synthesis. It is particularly valuable for carbon-carbon bond formation through Horner-Wadsworth-Emmons reactions, enabling the stereoselective synthesis of various organic molecules including purine nucleoside derivatives and galbonolide structures.
- IUPAC
- Chloro(diethoxyphosphinyl)acetic acid ethyl ester
- Synonyms
- Chloro(diethoxyphosphinyl)acetic acid ethyl ester
Horner-Wadsworth-Emmons Reactions
Triethyl 2-chloro-2-phosphonoacetate is a critical reagent for Horner-Wadsworth-Emmons olefination reactions, facilitating the formation of carbon-carbon double bonds with high stereoselectivity. This is instrumental in synthesizing complex molecules like vinylogous peptides and other unsaturated organic frameworks.
Synthesis of Purine Nucleoside Derivatives
This compound acts as a reactant in the synthesis of purine nucleoside derivatives that incorporate a halogen atom. This application is significant in medicinal chemistry for developing novel therapeutic agents.
Preparation of Bacterial Topoisomerase Inhibitors
It plays a role in the scale-up production of bacterial topoisomerase inhibitors, highlighting its utility in the synthesis of specialized antibacterial compounds.
Galbonolide Derivative Synthesis
Triethyl 2-chloro-2-phosphonoacetate is employed in the synthesis of galbonolide derivatives, showcasing its application in the construction of complex natural product scaffolds.
| Molecular weight | 258.64 |
|---|---|
| Linear formula | (C2H5O)2P(O)CH(Cl)CO2C2H5 |
| Assay | 97% |
| Boiling point | 93-95 °C/0.01 mmHg(lit.) |
| Density | 1.21 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.446(lit.) |
| Application | Reactant involved in:• Synthesis of purine nucleoside derivatives containing a halogen atom1• Horner-Wadsworth-Emmons reactions2,3• Scale-up production of bacterial topoisomerase inhibitors4• Synthesis of galbonolide derivatives5• Stereoselective Horner reaction for preparation of vinylogous peptides6 |
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 | 113 °C / 235.4 °F |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36/37/39 |
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-chloro-2-phosphonoacetate used for?
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Triethyl 2-chloro-2-phosphonoacetate is primarily used as a reagent in Horner-Wadsworth-Emmons reactions for C-C bond formation, olefination, and in the synthesis of purine nucleoside derivatives, bacterial topoisomerase inhibitors, and galbonolide derivatives.
What are the CAS number and molecular formula for Triethyl 2-chloro-2-phosphonoacetate?
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The CAS number is 7071-12-7, and the linear molecular formula is (C2H5O)2P(O)CH(Cl)CO2C2H5.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Triethyl 2-chloro-2-phosphonoacetate with an assay of 97%. This is a technical/research grade, and TSS does not represent it as USP, BP, or EP grade.
How should Triethyl 2-chloro-2-phosphonoacetate be handled safely?
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This compound may cause skin irritation (H315), serious eye irritation (H319), and respiratory irritation (H335). Always use appropriate personal protective equipment, including eyeshields, gloves, and suitable respiratory protection, and ensure adequate ventilation. Avoid breathing dust/fume/gas/mist/vapours/spray.
Is Triethyl 2-chloro-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-chloro-2-phosphonoacetate.
How can I request a quote or sample?
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Please contact our sales team directly to request a quote or a sample of Triethyl 2-chloro-2-phosphonoacetate.
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