ChemicalBook CAS DataBase List TETRAETHYL ETHYLENEDIPHOSPHONATE

TETRAETHYL ETHYLENEDIPHOSPHONATE synthesis

12synthesis methods

Product Name:TETRAETHYL ETHYLENEDIPHOSPHONATE
CAS Number:995-32-4
Molecular formula:C10H24O6P2
Molecular Weight:302.24

682-30-4 Synthesis

682-30-4
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762-04-9
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995-32-4
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$16.80/1G

Yield: 85%

Reaction Conditions:

with tributylphosphine in acetonitrile at 20; for 3 h;Concentration;Time;

Steps:

General procedure of phosphine-catalyzed hydrophosphorylation of O,O-dietylvinylphosphonate.
General procedure: To a solution of 0.004 mol of a hydrophosphoryl compound in 3 mL of acetonitrile and 30 mL of tributylphosphine,a solution of 0.004 mol of O,O-dietylvinylphosphonatein 7 mL of acetonitrile was added dropwise within 15 min with continuous stirring and cooling. The reaction mixture was kept in a water bath for 3 h. The reaction completeness was controlled by the 31P NMR spectroscopy. At the end of the reaction, the solvent was drivenaway at low pressure; the target product was isolated and purified according to one of the presented procedures (depending on the product aggregate state). Liquid products were isolated by vacuum distillation, during whichlow-boiling tributylphophine (which can be multiply usedas a catalyst in the reaction) and the target product wasseparated as a high-boiling fraction. The crystalline prod-uct of diphenylphosphine oxide addition was completely crystallized upon the acetonitrile vaporization at low pressure. The resulting powder was washed with pentane anddiethyl ether, filtered off, and dried at low pressure for6 h. Tributylphosphine was regenerated from pentane andether solution by distillation.Tetraethylethane-1,2-dialphosphonate (1). Yield85%, colorless liquid, bp 218° (1.5 mmHg). IR spectrum,ν, cm-1: 1243 s (P=), 1020 s (P--). 1 NMR spectrum,δ, ppm: 1.31 t (12, POCH2CH3, 3J = 7.1 Hz),1.92-1.99 m (4, PCH2), 4.04-4.17 m (8, PH2).13{1H} NMR spectrum, δ, ppm: 16.5 (P23),17.9-20.1 m (PCH2), 61.8 (P23). 31P{1H} NMRspectrum, δ, ppm: 29.4. Mass spectrum (ESI), m/z:303.1126 [ + H] (calculated for C10H25O6P2: 303.1126).Physical constants and spectral data coincide with thoseearlier described for this compound [38].

References:

Il’in;Antonova;Khusainova;Galkin [Russian Journal of General Chemistry,2019,vol. 89,# 11,p. 2207 - 2211][Zh. Obshch. Khim.,2019,vol. 89,# 11,p. 1686 - 1691,6]