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

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