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Chemical Structure| 3699-66-9 Chemical Structure| 3699-66-9
Chemical Structure| 3699-66-9

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Ethyl 2-(diethoxyphosphoryl)propanoate is Wittig-Horner reagent that condenses with a wide variety of aldehydes and ketones to form acrylates.

Synonyms: Triethyl 2-phosphonopropionate

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Product Details of Ethyl 2-(diethoxyphosphoryl)propanoate

CAS No. :3699-66-9
Formula : C9H19O5P
M.W : 238.22
SMILES Code : CCOC(=O)C(C)P(=O)(OCC)OCC
Synonyms :
Triethyl 2-phosphonopropionate
MDL No. :MFCD00009159
InChI Key :BVSRWCMAJISCTD-UHFFFAOYSA-N
Pubchem ID :107155

Safety of Ethyl 2-(diethoxyphosphoryl)propanoate

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Ethyl 2-(diethoxyphosphoryl)propanoate

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 3699-66-9 ]

[ 3699-66-9 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 3699-66-9 ]
  • [ 4395-92-0 ]
  • (Z)-4-(4-Isopropyl-phenyl)-2-methyl-but-2-enoic acid ethyl ester [ No CAS ]
  • 2
  • [ 3699-66-9 ]
  • [ 4395-92-0 ]
  • (E)-4-(4-Isopropyl-phenyl)-2-methyl-but-3-enoic acid ethyl ester [ No CAS ]
  • 3
  • [ 24686-78-0 ]
  • [ 3699-66-9 ]
  • [ 168888-64-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In tetrahydrofuran; mineral oil; (a) A solution of triethyl 2-phosphonopropionate (50.0 g) in dry tetrahydrofuran (75 ml) was added dropwise to a stirred suspension of sodium hydride (60percent in mineral oil, 8.0 g) in dry tetrahydrofuran (275 ml) under nitrogen and stirred at 20° C. for 10 minutes until a clear solution was formed. <strong>[24686-78-0]1-Benzoyl-4-piperidone</strong> (34.5 g) in dry tetrahydrofuran (75 ml) was added dropwise to the clear solution and the reaction mixture heated under reflux for 16 hours. After quenching the reaction mixture with 5M hydrochloric acid (20 ml), the resulting solid was removed by filtration. Excess ether was added to the filtrate, the aqueous layer separated off and the ethereal layer washed (water), dried, filtered and concentrated to give ethyl 2-(1-benzoyl-4-piperidylidene)propionate as an oil.
  • 4
  • [ 3699-66-9 ]
  • [ 109179-31-9 ]
  • C13H15BrO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
<Step 2>NaH (60percent assay, 193 mg, 4.82 mmol) was suspended in DMF (10 mL) and then cooled to 0° C. Triethyl 2-phosphonopropionate (1.05 mg, 4.82 mmol) in DMF (10 mL) was added dropwise in a slow manner to the solution and then stirred for 15 minutes. Then, the aldehyde obtained from Step 1 (640 mg, 3.22 mmol) in DMF (3 mL) was added thereto in a slow manner and then stirred for 18 hours while gradually heating it from 0° C. to room temperature. EtOAc was then added to the reaction solution, washed with water and saturated saline and then dried over anhydrous MgSO4. The solvent was eliminated in vacuo to obtain a residue. The resulting residue was then dissolved in THF (10 mL) and MeOH (4 mL), 2 N NaOH (8 mL, 8 mmol) was added thereto and then stirred at room temperature for 8 hours. The solvent was then eliminated in vacuo, 2 N HCl was added to acidify the solution and then the crystals precipitated were filtrated to obtain white crystals of the objective carboxylic acid (600 mg, 93percent).MS: 256
  • 5
  • [ 22929-52-8 ]
  • [ 3699-66-9 ]
  • ethyl 2-(dihydrofuran-3(2H)-ylidene)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.3 g Description 34Ethyl 2-(dihydrofuran-3(211)-ylidene)propanoate (D34)To a solution of sodium hydride (1.394 g) in THF (60 mL) at 0 °C was added dropwise ethyl 2-(diethoxyphosphoryl)propanoate (8.29 g) under N2. The mixture was stirred at 0°C for 30 mm until the mixture became clear, then <strong>[22929-52-8]dihydrofuran-3(2H)-one</strong> (1.5 g) was added. The mixture was stirred at RT for 2 hours and then quenched by water (100 mL). The mixture was extracted with EtOAc(3 x50 mL). The combined organic layer was washed with brine (100 mL), dried and evaporated under vacuum. The crude product was purified by column chromatography (silica gel, petroleum ether/EtOAc = 30:1) to afford the title compound (1.3 g). MS (ESI): C9H1403 requires 170; found 171 [M+H].
  • 6
  • [ 3699-66-9 ]
  • [ 5779-93-1 ]
  • ethyl 3-(2,3-dimethylphenyl)-2-methylacrylate [ No CAS ]
  • ethyl 3-(2,3-dimethylphenyl)-2-methylacrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium ethanolate; In ethanol; pentane; for 0.75h;Reflux; Cooling; Ethyl 2-(diethoxyphosphoryl)propanoate (80.0 g, 335 mmol, 1.5 eq) was added to a stirred solution of <strong>[5779-93-1]2,3-dimethylbenzaldehyde</strong> (30.0 g, 224 mmol, 1.0 eq) in pentane (300 mL) at room temperature. A solution of NaOEt (21percent w/w in EtOH, 109 mL, 293 mmol, 1.3 eq) was subsequently added dropwise under stirring, while cooling the reaction mixture with a water bath. Once the addition was completed, the resulting mixture was stirred at reflux for 45 minutes. The reaction mixture was then cooled to 0° C. and quenched by addition of aqueous NaOH (1 N , 300 mL). The organic layer was separated and washed again with NaOH (1 N, 300 mL). The combined aqueous layers were extracted with Et2O (3 x), washed with sat. aqueous NaHCO3, brine (twice), dried over MgSO4, filtered and concentrated in vacuo to afford an orange crude oil. Bulb-to bulb distillation (0.15 mbar, oven temp. 150-155° C.) afforded the product as a colorless oil (46.5 g, 213 mmol, 95percent yield; 94:6 mixture of E-Z isomers). 1H-NMR (major diastereoisomer):7.79 (s, 1H), 7.13-7.06 (m, 2H), 7.01 (m, J=3.00, m), 4.28 (q, J=7.13, 2H), 2.29 (s, 3H), 2.17 (s, 3H), 1.90 (d, J=1.40, 3H), 1.35 (t, J=7.13, 3H).
 

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