DIETHYLPHOSPHONOACETIC ACID

Bezeichnung:DIETHYLPHOSPHONOACETIC ACID

CAS-Nr3095-95-2

Englisch Name:DIETHYLPHOSPHONOACETIC ACID

CBNumberCB9724914

SummenformelC6H13O5P

Molgewicht196.14

MOL-Datei3095-95-2.mol

DIETHYLPHOSPHONOACETIC ACID physikalisch-chemischer Eigenschaften

Siedepunkt	150 °C/0.05 mmHg (lit.)
Dichte	1.220 g/mL at 25 °C (lit.)
Brechungsindex	n20/D 1.445(lit.)
Flammpunkt	>230 °F
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Aggregatzustand	Viscous Liquid
pka	3.48±0.10(Predicted)
Farbe	Clear colorless to yellow
Wichte	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

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/37/38
S-Sätze:	37/39-26
WGK Germany	3
HS Code	29319090

Gefahreninformationscode (GHS)

DIETHYLPHOSPHONOACETIC ACID Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
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].
Chemische Eigenschaften
clear colorless to yellow viscous liquid
Verwenden
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
Verwenden
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.
Vorbereitung Methode
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
Einzelnachweise
[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 Upstream-Materialien And Downstream Produkte

DIETHYLPHOSPHONOACETIC ACID Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

3095-95-2, DIETHYLPHOSPHONOACETIC ACID Verwandte Suche:

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