Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

B23261 Triethyl 2-phosphonopropionate, 98%

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

Stock No. Size Price ($) Quantity Availability
B23261-09 10g 37.90
B23261-18 50g 113.00
Add to Cart Add to Quote Request View Item

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
Storage & Sensitivity
Ambient temperatures.
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-H315-H319-H335

Combustible liquid. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P210-P235-P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep cool. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
1786994
Harmonized Tariff Code
2931.39
TSCA
No

Recommended

  • A10199

    L-Proline, 99%
  • A10249

    Tetra-n-butylammonium bromide, 98+%
  • A13760

    Trimethyl orthoformate, 99%
  • A15275

    Boron trifluoride diethyl etherate, 98+%
  • 31721

    Methanol, ACS, absolute, low acetone, 99.8+%

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware