potassium 3-ethoxy-3-oxopropanoate

• ChemBase ID: 77857
• Molecular Formular: C5H7KO4
• Molecular Mass: 170.20498
• Monoisotopic Mass: 169.99814038
• SMILES: O(CC)C(=O)CC(=O)[O-].[K+]
• Canonical SMILES: [O-]C(=O)CC(=O)OCC.[K+]
• InChI: InChI=1S/C5H8O4.K/c1-2-9-5(8)3-4(6)7;/h2-3H2,1H3,(H,6,7);/q;+1/p-1
• InChIKey: WVUCPRGADMCTBN-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium 3-ethoxy-3-oxopropanoate
• IUPAC Traditional name: potassium monoethyl malonate; potassium ion monoethyl malonate
• Synonyms: Monoethyl malonate potassium salt; Potassium monoethyl malonate; Ethyl potassium malonate; Malonic acid monoethyl ester potassium salt; potassium 3-ethoxy-3-oxopropanoate; Potassium 3-ethoxy-3-oxopropanoate; Ethyl potassium malonate; 丙二酸乙酯单钾盐; 丙二酸单乙酯 钾盐; 丙二酸单乙酯钾盐; 丙二酸单乙酯单钾盐

Database IDs

• CAS Number: 6148-64-7
• EC Number: 228-156-7
• MDL Number: MFCD00035603
• Beilstein Number: 3721682
• PubChem SID: 24862007; 24882593; 162042702
• PubChem CID: 3446434

CALCULATED PROPERTIES

• Acid pKa: 3.917031
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -1.4176992
• LogD (pH = 7.4): -3.0331244
• Log P: 0.17158474
• Molar Refractivity: 39.3426 cm^3
• Polarizability: 11.2780695 Å^3
• Polar Surface Area: 66.43 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 194 °C (dec.)(lit.); 194°C; 195-200 °C (dec.); ca 200°C dec.
• Hydrophobicity(logP): -2.62

Safety Information

• Storage Warning: Hygroscopic; Irritant/Hygroscopic
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.5% (NT); 95%; 98%
• Grade: purum
• Linear Formula: C2H5OCOCH2CO2K

DETAILS

Sigma Aldrich - 360899

Packaging
25, 100 g in poly bottle

REFERENCES

• An improved method for acylation with acid chlorides utilizes the Rathke MgCl₂-triethylamine reagent in acetonitrile or ethyl acetate to give ?-keto esters in very high yields: Synthesis, 290 (1993):
  
• Compare Diethyl malonate, A15468 and Dimethyl malonate, A11007, for other applications of this technique. See also Ethyl hydrogen malonate, A12627.
• Alternatively, ?-keto esters can be obtained in high yield by reaction with TMS chloride to generate ethyl trimethylsilyl malonate, followed by in situ reaction with acyl imidazoles or acyl chlorides in the presence of DBU: Tetrahedron Lett., 35, 9323 (1994).