Trimethyl phosphonoacetate
Trimethyl phosphonoacetate (CAS 5927-18-4) is a chemical reagent with the linear formula (CH3O)2P(O)CH2CO2CH3 and a molecular weight of 182.11 g/mol. It serves as a key reactant in various synthetic organic chemistry transformations. Its applications include facilitating C-C bond formation through reactions like the Horner-Wadsworth-Emmons olefination, Mannich-type reactions, and oxa-Michael additions, contributing to complex molecule synthesis.
- IUPAC
- (Carboxymethyl)phosphonic acid trimethyl ester,NSC 84262
- Synonyms
- (Carboxymethyl)phosphonic acid trimethyl esterTrimethyl ester of phosphonoacetic acid
Horner-Wadsworth-Emmons Reactions
Trimethyl phosphonoacetate is a crucial reagent in intramolecular Horner-Wadsworth-Emmons reactions, enabling the formation of carbon-carbon double bonds within molecular structures.
Mannich-Type Reactions
It participates in intramolecular Mannich-type reactions, which are instrumental in constructing the sarain A diazatricyclic core, a complex heterocyclic system.
Olefination
This compound is employed in olefination processes, including olefin cross-metathesis and heterocyclization reactions, for the synthesis of unsaturated organic compounds.
Michael Reactions
Trimethyl phosphonoacetate is utilized in organocatalytic oxa-Michael reactions, contributing to the formation of carbon-oxygen bonds in a stereoselective manner.
Oxindole Functionalisation
It is involved in the prenylation and geranylation of oxindoles, allowing for the introduction of isoprenoid side chains onto the oxindole scaffold.
| Molecular weight | 182.11 |
|---|---|
| Linear formula | (CH3O)2P(O)CH2CO2CH3 |
| Assay | ≥98.0% (GC) |
| Boiling point | 118 °C/0.85 mmHg(lit.)265-268 °C(lit.) |
| Density | 1.125 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.437(lit.)n20/D 1.437 |
| Application | Reactant involved in:• Intramolecular Mannich-type reactions to produce the sarain A diazatricyclic core1• Organocatalytic oxa-Michael reactions2• Prenylation and geranylation of oxindoles3• Intramolecular Horner-Wadsworth-Emmons reactions4,5• Olefin cross-metathesis / heterocyclization6 |
| 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 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 Trimethyl phosphonoacetate used for?
+
Trimethyl phosphonoacetate is used as a reactant in various synthetic organic chemistry transformations, including intramolecular Mannich-type reactions, organocatalytic oxa-Michael reactions, prenylation and geranylation of oxindoles, intramolecular Horner-Wadsworth-Emmons reactions, and olefin cross-metathesis/heterocyclization.
What is the CAS number and formula for Trimethyl phosphonoacetate?
+
The CAS number is 5927-18-4 and the linear formula is (CH3O)2P(O)CH2CO2CH3.
What grade and purity does Tech Serve Solutions supply?
+
Tech Serve Solutions supplies Trimethyl phosphonoacetate with an assay of ≥98.0% (GC). This product is not supplied as USP, BP, or EP grade.
What are the safety considerations when handling Trimethyl phosphonoacetate?
+
Handling Trimethyl phosphonoacetate requires appropriate personal protective equipment, including eyeshields, gloves, and a suitable respirator. It has a flash point of 113 °C (235.4 °F), indicating it is combustible.
How is Trimethyl phosphonoacetate shipped and exported?
+
Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals. Detailed information on shipping and export procedures for Trimethyl phosphonoacetate can be obtained by contacting our sales team.
How can I request a sample or quote for Trimethyl phosphonoacetate?
+
To request a sample or a quote for Trimethyl phosphonoacetate, please contact the Tech Serve Solutions sales department via our website or by phone.
▶ Related products
1-(2-Fluorobenzyl)piperazine
C11H15FN2
Chemical Synthesis
1-(2-Fluorophenyl)biguanide hydrochloride
Chemical Synthesis
1-(2-Fluorophenyl)cyclopropanecarboxylic acid
C10H9FO2
Chemical Synthesis
1-(2-Fluorophenyl)piperazine
C10H13FN2
Chemical Synthesis
1-(2-Fluorophenyl)piperazine monohydrochloride
C10H13FN2 · HCl
Chemical Synthesis
1-(2-Furoyl)-1H-benzotriazole
C11H7N3O2
Chemical Synthesis
1-(2-Furoyl)piperazine
C9H12N2O2
Chemical Synthesis
1-(2-Hydroxy-5-methylphenyl)-3-phenyl-1,3-propanedione
Chemical Synthesis
▶ Explore more
3-Methyl-1,5-di-p-tolyl-1,4-pentazadiene
Chemical Synthesis
3-Methyl-1,5-pentanediol
Chemical Synthesis
3-Methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine
C11H13N3
Chemical Synthesis
3-Methyl-1-(3′-sulfoamidophenyl)-5-pyrazolone
C10H11N3O3S
Chemical Synthesis