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| | Trimethyl phosphonoacetate Basic information |
| | Trimethyl phosphonoacetate Chemical Properties |
| Melting point | 242 °C | | Boiling point | 118 °C0.85 mm Hg(lit.) | | density | 1.125 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.437(lit.) | | Fp | >230 °F | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | form | Liquid | | Specific Gravity | approximate 1.265ｇ/ml (20℃) | | color | Clear colorless to light yellow | | Water Solubility | Slightly miscible with water. | | BRN | 1865177 | | InChI | 1S/C5H11O5P/c1-8-5(6)4-11(7,9-2)10-3/h4H2,1-3H3 | | InChIKey | SIGOIUCRXKUEIG-UHFFFAOYSA-N | | SMILES | COC(=O)CP(=O)(OC)OC | | LogP | -0.680 (est) | | CAS DataBase Reference | 5927-18-4(CAS DataBase Reference) | | NIST Chemistry Reference | Trimethyl phosphonoacetate(5927-18-4) | | EPA Substance Registry System | Acetic acid, (dimethoxyphosphinyl)-, methyl ester (5927-18-4) |
| Safety Statements | 23-24/25 | | WGK Germany | 3 | | F | 9 | | TSCA | TSCA listed | | HS Code | 29310095 | | Storage Class | 10 - Combustible liquids |
| | Trimethyl phosphonoacetate Usage And Synthesis |
| Chemical Properties | clear colorless to light yellow liquid | | Uses | Trimethyl phosphonoacetate is used in the preparation of sarin A by intramolecular Mannich-type reactions. It is involved in the Horner-Wadsworth-Emmons olefination with aldehydes and ketones to give acrylic esters. It is also involved in oxa-Michael reactions, prenylation of oxindoles and heterocyclization reactions. | | Application | Trimethyl phosphonoacetate is an important Wittig-horner reagent, which can be used to manufacture important intermediates of natural compounds such as vitamins, drugs, insect pheromones, etc.
Reactant involved in:
Intramolecular Mannich-type reactions to produce the sarain A diazatricyclic core
Organocatalytic oxa-Michael reactions
Prenylation and geranylation of oxindoles
Intramolecular Horner-Wadsworth-Emmons reactions
Olefin cross-metathesis / heterocyclization | | Definition | ChEBI: Trimethyl phosphonoacetate is a phosphonic ester. | | reaction suitability | reaction type: C-C Bond Formation | | Synthesis | The trimethyl phosphonoacetate is prepared from trimethyl phosphite and methyl chloroacetate through Michael Arbuzov rearrangement reaction. The synthetic method satisfies the chemical equations that CH2ClCOOH + CH3OH → CH5ClO2 + H2O, CH5ClO2 + C3H9O3P → C5H11O5P + CH3Cl. |
| | Trimethyl phosphonoacetate Preparation Products And Raw materials |
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