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.)

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)

InChIKey

DVQMPWOLBFKUMM-UHFFFAOYSA-N

SMILES

C(O)(=O)CP(OCC)(OCC)=O

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

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

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.

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

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

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(3095-95-2)Related Product Information

• Triethyl 2-chloro-2-phosphonoacetate
• BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE
• DIETHYLPHOSPHONOACETIC ACID ETHYL ESTER
• TRIETHYL 2-PHOSPHONOBUTYRATE
• TRIETHYL 2-PHOSPHONOPROPIONATE
• TRIETHYL 2-PHOSPHONOPENTANOATE
• DIETHYLPHOSPHONOACETIC ACID METHYL ESTER
• TRIMETHYLSILYL DIETHYLPHOSPHONOACETATE
• DIETHYLPHOSPHONOACETIC ACID
• Triethyl 2-fluoro-2-phosphonoacetate
• Triethyl phosphonobromoacetate
• DIETHYLPHOSPHONOACETIC ACID TERT-BUTYL ESTER
• DIETHYLPHOSPHONOACETIC ACID ETHYL ESTER
• PHOSPHONOACETIC ACID
• TRIETHYL ALPHA-PROPARGYLPHOSPHONOACETATE
• TRIETHYL PHOSPHONOACETATE-13C2
• TRIETHYL 2,2-DICHLORO-2-PHOSPHONOACETATE
• 2-ETHOXY-TRIETHYLPHOSPHONOACETATE