| Identification | Back Directory | [Name]
Ethyl dimethylphosphonoacetate | [CAS]
311-46-6 | [Synonyms]
Ethyl 2-(dimethoxyphosphoryl)
ETHYL DIMETHYLPHOSPHONOACETATE
EthylDimethylphosphonoacetate>
Dimethyl ethyl phosphonylacetate
ethyl 2-dimethoxyphosphorylacetate
ethyl (dimethoxyphosphinoyl)acetate
ETHYL DIMETHYLPHOSPHONOACETATE 98%
ethyl 2-dimethoxyphosphorylethanoate
Ethyl dimethyl phosphonoacetate, 98 %
Dimethylphosphonoacetic Acid Ethyl Ester
DIMETHYL(ETHOXYCARBONYLMETHYL)PHOSPHONATE
Dimethoxyphosphinylacetic acid ethyl ester
2-dimethoxyphosphorylacetic acid ethyl ester
(Dimethoxyphosphinyl)acetic acid ethyl ester
PHOSPHONOACETIC ACID P,P-DIMETHYL ETHYL ESTER
Dimethyl [(ethoxycarbonyl)methyl]phosphonate 98%
Acetic acid, 2-(dimethoxyphosphinyl)-, ethyl ester
ETHOXYCARBONYLMETHYLPHOSPHONIC ACID DIMETHYL ESTER
Ethyl (dimethoxyphosphoryl)acetate, Ethyl (dimethylphosphono)acetate
Ethoxycarbonylmethylphosphonic acid dimethylester, Phosphonoacetic acid P,P-dimethyl ethylester | [EINECS(EC#)]
206-222-6 | [Molecular Formula]
C6H13O5P | [MDL Number]
MFCD00015677 | [MOL File]
311-46-6.mol | [Molecular Weight]
196.14 |
| Chemical Properties | Back Directory | [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 Information | Back Directory | [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 |
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