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| | Ethyl dimethylphosphonoacetate Basic information |
| Product Name: | Ethyl dimethylphosphonoacetate | | Synonyms: | DIMETHYL(ETHOXYCARBONYLMETHYL)PHOSPHONATE;ETHOXYCARBONYLMETHYLPHOSPHONIC ACID DIMETHYL ESTER;ETHYL DIMETHYLPHOSPHONOACETATE;PHOSPHONOACETIC ACID P,P-DIMETHYL ETHYL ESTER;ethyl (dimethoxyphosphinoyl)acetate;ETHYL DIMETHYLPHOSPHONOACETATE 98%;Dimethylphosphonoacetic Acid Ethyl Ester;Ethyl dimethyl phosphonoacetate, 98 % | | CAS: | 311-46-6 | | MF: | C6H13O5P | | MW: | 196.14 | | EINECS: | 206-222-6 | | Product Categories: | | | Mol File: | 311-46-6.mol |  |
| | Ethyl dimethylphosphonoacetate Chemical Properties |
| Boiling point | 134 °C10 mm Hg(lit.) | | density | 1.188 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.435(lit.) | | Fp | 99 °C | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | form | clear liquid | | color | Colorless to Almost colorless | | BRN | 1777603 | | InChI | InChI=1S/C6H13O5P/c1-4-11-6(7)5-12(8,9-2)10-3/h4-5H2,1-3H3 | | InChIKey | HUNISAHOCCASGM-UHFFFAOYSA-N | | SMILES | C(OCC)(=O)CP(OC)(OC)=O |
| Hazard Codes | Xi | | Safety Statements | 23-24/25 | | WGK Germany | 3 | | HS Code | 2920907090 | | Storage Class | 10 - Combustible liquids |
| | Ethyl dimethylphosphonoacetate Usage And Synthesis |
| Uses | Reactant for synthesis of:
- Non-nucleoside inhibitors of HCV polymerase NS5B
- Neuropeptide Y1 receptor antagonists
- Alkenylcarboxylates from Horner-Wadsworth-Emmons reactions
Reactant for:
- Enantioselective transfer hydrogenation for preparation of the C7-C14 fragment of ulapualide A
- Intramolecular Michael reactions
- Olefination of peptidyl aldehydes with stabilized ylides
| | Application |
Ethyl dimethylphosphonoacetate could prepare a temporary plugging agent with hydroxyethylpyrrolidone and ethyl perfluorobutyl ether. The temporary plugging agent is useful for oil-water wells.
| | reaction suitability | reaction type: C-C Bond Formation | | Synthesis | The general procedure for the synthesis of ethyl dimethylphosphonoacetate from ethyl chloroacetate and trimethoxyphosphorus is as follows: a dry and clean 500 mL coil was heated to 150 °C. Take 1000g (0.7 eq., 8.16 mol) of ethyl chloroacetate (boiling point 142~145°C at standard atmospheric pressure) in reaction flask A and dilute it by adding 4000g of toluene. Another 1417g (1.0 eq., 11.42mol) of trimethoxyphosphine (boiling point at 112°C under standard atmospheric pressure) was placed in reaction vial B, and 3583g of toluene was added for dilution. After the coil temperature was stabilized, pump A (mixed solution of ethyl chloroacetate and toluene) and pump B (mixed solution of trimethoxyphosphine and toluene) were activated, both at a flow rate of 25.0 g/min. The residence time of the reactants in the reactor was 10 min, and the reaction pressure was maintained at 0.5~2.0 MPa. Upon completion of the reaction, the discharge port was directly connected to the thin-film evaporation device, and the evaporation pressure was controlled to 4~ 10×102 Pa, and the temperature was 95~105°C. Finally, 1344 g of ethyl dimethylphosphonoacetate (boiling point of 110~112°C, 466 Pa) was obtained with a yield of 84%. | | References | [1] Patent: CN107163079, 2017, A. Location in patent: Paragraph 0068; 0069; 0070; 0071
[2] Bulletin de la Societe Chimique de France, 1965, p. 1925 - 1930
[3] Tetrahedron Letters, 1999, vol. 40, # 8, p. 1455 - 1458 |
| | Ethyl dimethylphosphonoacetate Preparation Products And Raw materials |
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