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268127

Sigma-Aldrich

Diethylphosphonoacetic acid

95%

Synonym(s):

(Diethoxyphosphinyl)acetic acid, Diethyl carboxymethylphosphonate, NSC 272281

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About This Item

Linear Formula:
(C2H5O)2P(O)CH2CO2H
CAS Number:
Molecular Weight:
196.14
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

95%

form

liquid

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.445 (lit.)

bp

150 °C/0.05 mmHg (lit.)

density

1.220 g/mL at 25 °C (lit.)

SMILES string

CCOP(=O)(CC(O)=O)OCC

InChI

1S/C6H13O5P/c1-3-10-12(9,11-4-2)5-6(7)8/h3-5H2,1-2H3,(H,7,8)

InChI key

DVQMPWOLBFKUMM-UHFFFAOYSA-N

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Application

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
Used to make phosphonoester intermediates for intramolecular HEW reactions.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Journal of the American Chemical Society, 113, 3850-3850 (1991)
Tetrahedron Asymmetry, 1, 137-137 (1990)

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