268127

Diethylphosphonoacetic acid

95%

• Synonym(s): (Diethoxyphosphinyl)acetic acid, Diethyl carboxymethylphosphonate, NSC 272281
• Linear Formula: (C₂H₅O)₂P(O)CH₂CO₂H
• CAS Number: 3095-95-2
• Molecular Weight: 196.14
• MDL number: MFCD00192032
• UNSPSC Code: 12352108
• PubChem Substance ID: 24856264
• NACRES: NA.22

Properties

• 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

Description

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.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves