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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 |
| Hazard Codes | Xn | | Risk Statements | 22-36/37/38 | | Safety Statements | 37/39-26 | | WGK Germany | 3 | | HS Code | 29319090 | | Storage Class | 10 - Combustible liquids | | Hazard Classifications | Acute Tox. 4 Oral |
| | 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. | | Production Methods | Diethylphosphonoacetic acid is synthesised using triethyl phosphonoacetate as a raw material by chemical reaction. The specific synthesis steps are as follows:
After dissolving triethyl phosphonoacetate (1.7 g, 7.5 mmol) in ethanol / water (15 mL ie 14: 1) at room temperature, potassium hydroxide (424.2 mg, 7.56 mmol, ) 6597-4400) was added and stirred at room temperature. The reaction was neutralized with 1N HCl to pH 4, the ethanol was removed by distillation under reduced pressure, diluted with chloroform (20 mL), washed with water (10 mL) and saturated brine (10 mL). The separated organic layer was dried over anhydrous sodium sulfate, filtered and distilled under reduced pressure to obtain 2-(diethoxyphosphoryl)acetic acid 4 (1.48 gm, 100percent).
 | | Synthesis Reference(s) | Journal of the American Chemical Society, 102, p. 4534, 1980 DOI: 10.1021/ja00533a047 | | reaction suitability | reaction type: C-C Bond Formation | | 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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