ChemicalBook > CAS DataBase List > DIETHYLPHOSPHONOACETIC ACID

DIETHYLPHOSPHONOACETIC ACID

Product Name
DIETHYLPHOSPHONOACETIC ACID
CAS No.
3095-95-2
Chemical Name
DIETHYLPHOSPHONOACETIC ACID
Synonyms
2-(diethoxyphosphoryl)acetic acid;NSC 272281;Diethyl sulfonic acid;Venadaparib Impurity 39;Mirogabalin Impurity 60;acetyl diethyl phosphate;Diethylphosphoacetic acid;2-diethoxyphosphorylacetate;(diethoxyphosphoryl)acetate;DIETHYLPHOSPHONOACETIC ACID
CBNumber
CB9724914
Molecular Formula
C6H13O5P
Formula Weight
196.14
MOL File
3095-95-2.mol
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DIETHYLPHOSPHONOACETIC ACID Property

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
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Safety

Hazard Codes 
Xn
Risk Statements 
22-36/37/38
Safety Statements 
37/39-26
WGK Germany 
3
HS Code 
29319090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
268127
Product name
Diethylphosphonoacetic acid
Purity
95%
Packaging
5ml
Price
$18.76
Updated
2024/03/01
Sigma-Aldrich
Product number
268127
Product name
Diethylphosphonoacetic acid
Purity
95%
Packaging
25ml
Price
$143
Updated
2024/03/01
TRC
Product number
D444745
Product name
Diethylphosphonoacetic acid
Packaging
25g
Price
$140
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
ING0004122
Product name
DIETHYLPHOSPHONOACETIC ACID
Purity
95.00%
Packaging
5ML
Price
$775.24
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
ING0004122
Product name
DIETHYLPHOSPHONOACETIC ACID
Purity
95.00%
Packaging
25ML
Price
$1112.15
Updated
2021/12/16
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DIETHYLPHOSPHONOACETIC ACID Chemical Properties,Usage,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

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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DIETHYLPHOSPHONOACETIC ACID Suppliers

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View Lastest Price from DIETHYLPHOSPHONOACETIC ACID manufacturers

Nanjing Fred Technology Co., Ltd
Product
2-(Diethoxyphosphinyl)acetic acid 3095-95-2
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1 ton
Release date
2023-12-20
Hebei Chuanghai Biotechnology Co,.LTD
Product
DIETHYLPHOSPHONOACETIC ACID 3095-95-2
Price
US $5.00-2.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10000kg
Release date
2024-08-19
Shaanxi Dideu Medichem Co. Ltd
Product
DIETHYLPHOSPHONOACETIC ACID 3095-95-2
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20T
Release date
2024-08-10

3095-95-2, DIETHYLPHOSPHONOACETIC ACIDRelated Search:

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

  • DIETHYLPHOSPHONOACETIC ACID
  • DIETHYLPHOSPHONOETHANOIC ACID
  • (DIETHOXYPHOSPHINOYL)ACETIC ACID
  • DIETHYLCARBOXYMETHYLPHOSPHONATE
  • Diethylcarboxymethylphosphonate, 98 %
  • 2-diethoxyphosphorylacetate
  • Diethylphosphoacetic acid
  • (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
  • 2-(diethoxyphosphoryl)acetic acid
  • Diethoxyphosphorylacetic acid
  • Diethyl carboxymethanephosphonate
  • Phosphono-acetic acid P,P-diethyl ester
  • Acetic acid,2-(diethoxyphosphinyl)-
  • Diethylphosphonoacetic acid 95%
  • NSC 272281
  • DIETHYLPHOSPHONOACETIC ACID(3095-95-2)
  • 2-diethoxyphosphorylaceticaci
  • Diethyl sulfonic acid
  • Venadaparib Impurity 39
  • Mirogabalin Impurity 60
  • 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