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| | DIETHYLPHOSPHONOACETIC ACID Basic information |
| | DIETHYLPHOSPHONOACETIC ACID Chemical Properties |
| Boiling point | 150 °C/0.05 mmHg (lit.) | | density | 1.220 g/mL at 25 °C (lit.) | | refractive index | n20/D 1.445(lit.) | | Fp | >230 °F | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | form | Viscous Liquid | | pka | 3.48±0.10(Predicted) | | color | Clear colorless to yellow | | Specific Gravity | 1.220 | | InChI | InChI=1S/C6H13O5P/c1-3-10-12(9,11-4-2)5-6(7)8/h3-5H2,1-2H3,(H,7,8) | | InChIKey | DVQMPWOLBFKUMM-UHFFFAOYSA-N | | SMILES | C(O)(=O)CP(OCC)(OCC)=O |
| | DIETHYLPHOSPHONOACETIC ACID Usage And Synthesis |
| Description | Diethylphosphonoacetic Acid (DPA) is a Horner-Wadsworth-Emmons (HWE) reagent. The mixed anhydride of trifluoroacetic acid—diethylphosphonoacetic acid Treat a 21-hydroxy-20-keto steroid leads directly to cardenolides by an intramolecular Horner-Emmons reaction. It could also used as a dummy template to prepare a molecularly imprinted polymer for use as an artificial receptor for organophosphorus pesticides (OPPs)[1-3]. | | Chemical Properties | clear colorless to yellow viscous liquid | | Uses | Acts as a nucleophile for nucleophilic addition reactions for synthesis of allene epoxides
Reactant for:
- Stereoselectivity studies of the Staudinger reaction
- Enantioselective formation of diols via epoxidation and hydration reactions
- Horner-Wadsworth-Emmons reactions
- Remote chelation controlled Ireland-Claisen rearrangement
- Ugi-Dieckmann reactions for synthesis of tetramic acid derivatives
| | Uses | Diethylphosphonoacetic Acid is a reagent that is used for enantioselective preparation of α-phosphoryl-α,β-unsatd.-δ-aryl-δ-lactones from nonracemic β-hydroxyaldehydes and their conversion to α-methylene-δ-aryl-δ-lactones. | | Synthesis Reference(s) | Journal of the American Chemical Society, 102, p. 4534, 1980 DOI: 10.1021/ja00533a047 | | References | [1] S. Donovan, J. Mcmurry, M. Avery. “Synthesis of digitoxigenin by remote functionalization.” Tetrahedron Letters 20 1 (1979): 3287–3290.
[2] A. M. Boldi, Hisham O. Eissa, Charles R. Johnson. “Solid-phase library synthesis of triazolopyridazines via [4+2] cycloadditions.” Tetrahedron Letters 40 1 (1999): 619–622.
[3] Lu Zhang. “Preparation and Characterization of Broad-Spectrum Artificial Antibody for OPPs Based on Dummy Template Imprinting Technique.” International Journal of Polymer Analysis and Characterization 117 1 (2014): 510–521. |
| | DIETHYLPHOSPHONOACETIC ACID Preparation Products And Raw materials |
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