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: 2026-01-13 11:27:08

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	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)

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.