ChemicalBook Product Catalog Chemical Reagents Organic reagents Phosphorus-containing compound DIETHYLPHOSPHONOACETIC ACID

DIETHYLPHOSPHONOACETIC ACID

DIETHYLPHOSPHONOACETIC ACID Basic information
Product Name:DIETHYLPHOSPHONOACETIC ACID
Synonyms:DIETHYLPHOSPHONOACETIC ACID;DIETHYLPHOSPHONOETHANOIC ACID;(DIETHOXYPHOSPHINOYL)ACETIC ACID;DIETHYLCARBOXYMETHYLPHOSPHONATE;Diethylcarboxymethylphosphonate, 98 %;(diethoxyphosphoryl)acetate;(Diethoxyphosphinyl)acetic acid;2-(Diethoxyphosphinyl)acetic acid
CAS:3095-95-2
MF:C6H13O5P
MW:196.14
EINECS:608-560-3
Product Categories:Horner-Wadsworth-Emmons Reagents;Olefination;C-C Bond Formation
Mol File:3095-95-2.mol
DIETHYLPHOSPHONOACETIC ACID Structure
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.)
Fp >230 °F
storage temp. Keep in dark place,Sealed in dry,Room Temperature
form Viscous Liquid
pka3.48±0.10(Predicted)
color Clear colorless to yellow
Specific Gravity1.220
Safety Information
Hazard Codes Xn
Risk Statements 22-36/37/38
Safety Statements 37/39-26
WGK Germany 3
HS Code 29319090
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
DIETHYLPHOSPHONOACETIC ACID Usage And Synthesis
Chemical Propertiesclear colorless to yellow viscous liquid
UsesActs 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
UsesDiethylphosphonoacetic 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.
Synthesis Reference(s)Journal of the American Chemical Society, 102, p. 4534, 1980 DOI: 10.1021/ja00533a047
DIETHYLPHOSPHONOACETIC ACID Preparation Products And Raw materials
Preparation ProductsDIETHYL VINYLPHOSPHONATE-->4-METHYLPENT-2-ENOIC ACID-->Methyl diethylphosphonoacetate-->Monoethyl fumarate-->Diethyl (benzyloxycarbonylmethyl)phosphonate, 98 %-->ALLYL DIETHYLPHOSPHONOACETATE
Triethyl 2-chloro-2-phosphonoacetate DIETHYLPHOSPHONOACETIC ACID ETHYL ESTER TRIETHYL 2-PHOSPHONOPROPIONATE BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE TRIETHYL ALPHA-PROPARGYLPHOSPHONOACETATE DIETHYLPHOSPHONOACETIC ACID ETHYL ESTER ALLYL DIETHYLPHOSPHONOACETATE TRIETHYL 2-PHOSPHONOPENTANOATE DIISOPROPYL (ETHOXYCARBONYLMETHYL)PHOSPHONATE TRIETHYL PHOSPHONOACETATE-2-13C DIETHYLPHOSPHONOACETIC ACID TERT-BUTYL ESTER TRIETHYL 2-PHOSPHONOBUTYRATE 2-ETHOXY-TRIETHYLPHOSPHONOACETATE TRIETHYL PHOSPHONOACETATE-1-13C TRIETHYL PHOSPHONOACETATE-13C2 Triethyl 2-fluoro-2-phosphonoacetate TRIMETHYLSILYL DIETHYLPHOSPHONOACETATE DIETHYLPHOSPHONOACETIC ACID
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