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3699-66-9 - Triethyl 2-phosphonopropionate, 98% - Diethyl 1-(ethoxycarbonyl)ethanephosphonate - 2-Phosphonopropionic acid triethyl ester - B23261 - Alfa Aesar

B23261 Triethyl 2-phosphonopropionate, 98%

CAS Number
3699-66-9
Synonyms
Diethyl 1-(ethoxycarbonyl)ethanephosphonate
2-Phosphonopropionic acid triethyl ester

Size Price ($) Quantity Availability
10g 34.72
50g 110.21
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Triethyl 2-phosphonopropionate, 98%

MDL
MFCD00009159
EINECS
223-033-4

Chemical Properties

Formula
C9H19O5P
Formula Weight
238.22
Boiling Point
143-144°/12mm
Flash Point
88°(190°F)
Density
1.111
Refractive Index
1.4320
Solubility
Miscible with chloroform and methanol.

Applications

Triethyl 2-phosphonopropionate is used as a reactant in intramolecular conjugate addition for the synthesis of floresolide B, enantioselective synthesis of spiroindane di-methyl acetic acid and in stereo selective intramolecular Diels-Alder reactions. It plays an important role in Horner-Wadsworth-Emmons reactions and chemoenzymatic one-pot synthesis of gamma-butyrolactones. It is also used in the preparation of 3-[2]furyl-2-methyl-acrylic acid ethyl ester by reacting with furfural.

Notes

Incompatible with strong bases.

Literature References

Wadsworth-Emmons precursor of methacrylic esters (see Triethyl­ phosphonoacetate, A14120 and Appendix 1). Lithiation followed by acylation with perfluoroalkanoic anhydrides gives a perfluoroacyl intermediate which, with an organolithium reagent, leads stereoselectively to a trifluoroalkylated ɑß-unsaturated ester: J. Fluorine Chem., 89, 141 (1998):

Sharpe, M. A.; Han, J.; Baskin, A. M.; Baskin, D. S. Design and Synthesis of a MAO-B-Selectively Activated Prodrug Based on MPTP: A Mitochondria-Targeting Chemotherapeutic Agent for Treatment of Human Malignant Gliomas. ChemMedChem 2015, 10 (4), 621-628.

Shouksmith, A. E.; Evans, L. E.; Tweddle, D. A.; Miller, D. C.; Willmore, E.; Newell, D. R.; Golding, B. T.; Griffin, R. J. Synthesis and Activity of Putative Small-molecule Inhibitors of the F-box Protein SKP2. Aust. J. Chem. 2015, 68 (4), 660-679.

GHS Hazard and Precautionary Statements

Hazard Statements: H227

Combustible liquid.

Precautionary Statements: P210-P280-P370+P378a-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. In case of fire: Use for extinction: CO2, powder or water spray. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1786994
Harmonized Tariff Code
2931.90
TSCA
No

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