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DIETHYLPHOSPHONOACETIC ACID

CAS No.
3095-95-2
Chemical Name:
DIETHYLPHOSPHONOACETIC ACID
Synonyms
2-(diethoxyphosphoryl)acetic acid;NSC 272281;Diethyl sulfonic acid;Venadaparib Impurity 39;acetyl diethyl phosphate;Diethylphosphoacetic acid;(diethoxyphosphoryl)acetate;DIETHYLPHOSPHONOACETIC ACID;2-diethoxyphosphorylacetate;DIETHYLPHOSPHONOETHANOIC ACID
CBNumber:
CB9724914
Molecular Formula:
C6H13O5P
Molecular Weight:
196.14
MDL Number:
MFCD00192032
MOL File:
3095-95-2.mol
MSDS File:
SDS
Last updated:2024-09-05 14:18:45

DIETHYLPHOSPHONOACETIC ACID 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)
color Clear colorless to yellow
Specific Gravity 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
FDA UNII 6L31G8862Z

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338
Hazard Codes  Xn
Risk Statements  22-36/37/38
Safety Statements  37/39-26
WGK Germany  3
HS Code  29319090

DIETHYLPHOSPHONOACETIC ACID price More Price(35)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 268127 Diethylphosphonoacetic acid 95% 3095-95-2 5ml $18.76 2024-03-01 Buy
Sigma-Aldrich 268127 Diethylphosphonoacetic acid 95% 3095-95-2 25ml $143 2024-03-01 Buy
TRC D444745 Diethylphosphonoacetic acid 3095-95-2 25g $140 2021-12-16 Buy
American Custom Chemicals Corporation ING0004122 DIETHYLPHOSPHONOACETIC ACID 95.00% 3095-95-2 5ML $775.24 2021-12-16 Buy
American Custom Chemicals Corporation ING0004122 DIETHYLPHOSPHONOACETIC ACID 95.00% 3095-95-2 25ML $1112.15 2021-12-16 Buy
Product number Packaging Price Buy
268127 5ml $18.76 Buy
268127 25ml $143 Buy
D444745 25g $140 Buy
ING0004122 5ML $775.24 Buy
ING0004122 25ML $1112.15 Buy

DIETHYLPHOSPHONOACETIC ACID Chemical Properties,Uses,Production

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

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

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.

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).
DIETHYLPHOSPHONOACETIC ACID synthesis

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.

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View Lastest Price from DIETHYLPHOSPHONOACETIC ACID manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2-(Diethoxyphosphinyl)acetic acid pictures 2024-09-14 2-(Diethoxyphosphinyl)acetic acid
3095-95-2
US $0.00-0.00 / kg 1kg 98% 1 ton Nanjing Fred Technology Co., Ltd
DIETHYLPHOSPHONOACETIC ACID pictures 2024-08-19 DIETHYLPHOSPHONOACETIC ACID
3095-95-2
US $5.00-2.00 / KG 1KG 99% 10000kg Hebei Chuanghai Biotechnology Co,.LTD
DIETHYLPHOSPHONOACETIC ACID pictures 2024-08-11 DIETHYLPHOSPHONOACETIC ACID
3095-95-2
US $1.00 / KG 1KG 99% 20T Shaanxi Dideu Medichem Co. Ltd
DIETHYLPHOSPHONOACETIC ACID DIETHYLPHOSPHONOETHANOIC ACID (DIETHOXYPHOSPHINOYL)ACETIC ACID DIETHYLCARBOXYMETHYLPHOSPHONATE Diethylcarboxymethylphosphonate, 98 % (diethoxyphosphoryl)acetate (Diethoxyphosphinyl)acetic acid 2-(Diethoxyphosphinyl)acetic acid Diethylphosphonoacetic acid,98% (Diethoxyphosphoryl)acetic acid, Diethylphosphonoacetic acid Diethyl (hydroxycarbonylmethyl)phosphonate acetyl diethyl phosphate Diethylphosphonoacetic acid, 98% 25GR Diethoxyphosphorylacetic acid Diethyl carboxymethanephosphonate Phosphono-acetic acid P,P-diethyl ester Acetic acid,2-(diethoxyphosphinyl)- Diethylphosphonoacetic acid 95% NSC 272281 2-diethoxyphosphorylacetate Diethylphosphoacetic acid DIETHYLPHOSPHONOACETIC ACID(3095-95-2) 2-diethoxyphosphorylaceticaci Diethyl sulfonic acid 2-(diethoxyphosphoryl)acetic acid Venadaparib Impurity 39 3095-95-2 3095-95-5 C6H13O5P C2H5O2POCH2CO2H Synthetic Reagents Olefination Horner-Wadsworth-Emmons Reagents C-C Bond Formation Horner-Wadsworth-Emmons Reagents Olefination C-C Bond Formation