DIETHYLPHOSPHONOACETIC ACID
Synonym(s):(Diethoxyphosphinyl)acetic acid;Diethyl carboxymethylphosphonate;NSC 272281
- CAS NO.:3095-95-2
- Empirical Formula: C6H13O5P
- Molecular Weight: 196.14
- MDL number: MFCD00192032
- EINECS: 608-560-3
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-09-05 14:18:45
What is DIETHYLPHOSPHONOACETIC ACID?
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
The Uses of DIETHYLPHOSPHONOACETIC ACID
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.
The Uses of DIETHYLPHOSPHONOACETIC ACID
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
What are the applications of Application
Diethylphosphonoacetic acid is a nucleophile for nucleophilic addition reactions
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.
Properties of DIETHYLPHOSPHONOACETIC ACID
Boiling point: | 150 °C/0.05 mmHg (lit.) |
Density | 1.220 g/mL at 25 °C (lit.) |
refractive index | n |
Flash point: | >230 °F |
storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
form | Viscous Liquid |
pka | 3.48±0.10(Predicted) |
Specific Gravity | 1.220 |
color | Clear colorless to yellow |
InChI | InChI=1S/C6H13O5P/c1-3-10-12(9,11-4-2)5-6(7)8/h3-5H2,1-2H3,(H,7,8) |
Safety information for DIETHYLPHOSPHONOACETIC ACID
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for DIETHYLPHOSPHONOACETIC ACID
InChIKey | DVQMPWOLBFKUMM-UHFFFAOYSA-N |
SMILES | C(O)(=O)CP(OCC)(OCC)=O |
New Products
2,2-diethoxyethanethioamide Tubulysin F Tubulysin E Tubulysin G 1,2,3,6-TETRAHYDROPYRIDINE HYDROCHLORIDE 4-(Benzyloxy)-3-bromophenylacetic Acid Methyl (R)-1-Boc-4,4-difluoropyrrolidine-2-carboxylate 2,2-Difluoropropylamine hydrochloride 2,2-Difluoropropanol 2H-Pyran, 4-ethynyltetrahydro- 2-[2-[3(S)-3[2-(7-chloro-2-quinolinyl) ethenyl] phenyl-3- hydroxyl propyl] phenyl]-2-propanol Imeglimin Hydrochloride IH Fuel shell Calcium Sodium Phosphosilicate IH 2-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol ethanedioate 2-(1-(Mercaptomethyl) cyclopropyl) acetonitrile Lubiprostone Latanoprostene Bunod Magnesium Trisilicate Flame Retardant Zinc Borate methyl 3-fluoro-4- thiomorpholino phenylcarbamate (R)-(3-(3-fluoro-4- thiomorpholinophenyl)-2- oxooxazolidin-4-yl) methyl methanesulfonate 1H-Imidazole-4-carbonitrile 7-Methoxyquinoline-4-carbonitrileRelated products of tetrahydrofuran
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