Triethyl phosphonoacetate
Triethyl phosphonoacetate (CAS: 867-13-0) is an organophosphorus compound with the molecular formula (C2H5O)2P(O)CH2CO2C2H5 and a molecular weight of 224.19 g/mol. This versatile reagent is widely employed in organic synthesis, particularly as a key component in Horner-Wadsworth-Emmons reactions for the stereoselective synthesis of alkenes. Its applications extend to various C-C bond-forming reactions, making it valuable in the production of pharmaceuticals and fine chemicals.
- IUPAC
- (Diethoxyphosphinyl)acetic acid ethyl ester,Diethyl ethoxycarbonylmethylphosphonate,NSC 13898,NSC 16128,Triethyl carboxymethylphosphonate
- Synonyms
- (Diethoxyphosphinyl)acetic acid ethyl esterDiethyl ethoxycarbonylmethylphosphonateNSC 13898NSC 16128Triethyl carboxymethylphosphonate
Horner-Wadsworth-Emmons Reactions
This reagent is a critical component in Horner-Wadsworth-Emmons reactions, facilitating the stereoselective formation of alkenes. It is used to introduce the phosphonate ester moiety, which subsequently undergoes base-induced elimination to yield the desired olefin.
Intramolecular Cyclizations
Triethyl phosphonoacetate participates in various intramolecular cyclization reactions, including Heck-type cyclizations and aryne-ene reactions. These processes are instrumental in constructing cyclic organic frameworks.
Tsuji-Trost Type Reactions
The compound serves as a reactant in Tsuji-Trost type allylic alkylation reactions. This application is significant for forming new carbon-carbon bonds and functionalizing allylic systems.
Synthesis of Aldehydes
It is utilised in synthetic pathways leading to the formation of aldehydes. This application highlights its utility in multi-step organic syntheses where aldehyde functionalities are required.
| Molecular weight | 224.19 |
|---|---|
| Linear formula | (C2H5O)2P(O)CH2CO2C2H5 |
| Assay | ≥97.0% (GC) |
| Boiling point | 142-145 °C/9 mmHg(lit.) |
| Density | 1.13 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.431(lit.)n20/D 1.432 |
| Application | Reactant involved in:• Horner-Wadsworth-Emmons reactions1,2• Intramolecular Heck-type cyclization and isomerizations3• Tsuji-Trost type reactions4• Intramolecular aryne-ene reactions5• Synthesis of aldehydes6 |
| Protective equipment | Eyeshields, Gloves |
|---|---|
| Flash point | 105 °C / 221 °F |
| Transport (UN / ADR) | UN 3082 9 / PGIII |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | N |
| Risk statements (R) | 51/53 |
| Safety statements (S) | 61 |
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 phosphonoacetate used for?
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Triethyl phosphonoacetate (CAS: 867-13-0) is primarily used as a reagent in organic synthesis, notably in Horner-Wadsworth-Emmons reactions for alkene synthesis, as well as in various cyclization and alkylation reactions.
What is the CAS number and formula for Triethyl phosphonoacetate?
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The CAS number for Triethyl phosphonoacetate is 867-13-0, and its linear formula is (C2H5O)2P(O)CH2CO2C2H5.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Triethyl phosphonoacetate with an assay of ≥97.0% (GC). This product is typically supplied for research and industrial applications and is not represented as USP, BP, or EP grade unless explicitly stated.
How should Triethyl phosphonoacetate be handled?
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Triethyl phosphonoacetate is harmful if swallowed and may cause skin and eye irritation. Appropriate personal protective equipment, including eyeshields and gloves, should be worn. It is classified as WGK 2 in Germany and has specific transport regulations (UN 3082 9 / PGIII).
Is Triethyl phosphonoacetate shipped internationally?
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Yes, Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals, including Triethyl phosphonoacetate, and can facilitate international shipments.
How can I request a quote or sample for Triethyl phosphonoacetate?
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To request a quote or a sample of Triethyl phosphonoacetate, please contact our sales team through the TSS website or by calling our customer service line.
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