3-ethoxy-3-oxopropanoic acid

• ChemBase ID: 123201
• Molecular Formular: C5H8O4
• Molecular Mass: 132.11462
• Monoisotopic Mass: 132.04225874
• SMILES: C(C(=O)O)C(=O)OCC
• Canonical SMILES: CCOC(=O)CC(=O)O
• InChI: InChI=1S/C5H8O4/c1-2-9-5(8)3-4(6)7/h2-3H2,1H3,(H,6,7)
• InChIKey: HGINADPHJQTSKN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-ethoxy-3-oxopropanoic acid
• IUPAC Traditional name: ethyl hydrogen malonate
• Synonyms: Monoethyl malonate; 3-ethoxy-3-oxopropanoic acid; (Ethoxycarbonyl)acetic acid; 3-Ethoxy-3-oxopropanoic acid; Ethyl hydrogen malonate; Ethyl malonate; Monoethyl hydrogen malonate; mono-Ethyl malonate; ETHYL HYDROGEN MALONATE; Malonic acid monoethyl ester; Monoethyl malonate; Ethyl hydrogen malonate; 丙二酸单乙酯; 丙二酸氢乙酯

Database IDs

• CAS Number: 1071-46-1
• EC Number: 213-992-7
• MDL Number: MFCD00020490
• Beilstein Number: 1758845
• PubChem SID: 162217554; 24868159
• PubChem CID: 70615

CALCULATED PROPERTIES

• Acid pKa: 3.917031
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.4176992
• LogD (pH = 7.4): -3.0331244
• Log P: 0.17158474
• Molar Refractivity: 28.5055 cm^3
• Polarizability: 11.39605 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Liquid
• Melting Point: 200 - 202°C
• Boiling Point: 106.5 °C/3 mmHg(lit.); 106°C/3mm
• Flash Point: >110°C(230°F); 113 °C; 235.4 °F
• Density: 1.119; 1.119 g/mL at 25 °C(lit.)
• Refractive Index: 1.4295; n20/D 1.435(lit.)
• Hydrophobicity(logP): 0.352

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37-60
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: 90+%; 95%; 96%; 98%
• Impurities: <10% ethyl malonate, potassium salt
• Linear Formula: HO2CCH2CO2C2H5

DETAILS

Sigma Aldrich - 445088

Packaging
5 g in glass bottle
Application
Reactant for:
• Preparation of tetramic acids via Dieckmann ring closure1
• Organocatalytic decarboxylative Doebner-Knoevenagel reactions2
• Conjugation to amino-modified oligonucleotides3
• Acylation reactions (acylation agent)4
• Indole glyoxylamides for potential Prion disease treatment5
• Knoevenagel condensation with aldehydes6
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 445088.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

• Carbodiimide coupling with polymer-bound ɑ-amino acids has been used in the solid-phase synthesis of substituted tetramic acids; J. Org. Chem., 63, 4808 (1998).
• See also Ethyl potassium malonate, A10720.
• Half esters of malonic acid react with ɑ?-enals in pyridine/DMAP to give ɑ? δ-dienoic esters with good (E)-selectivity: Synthesis: 534 (1988).
• Reaction with alkyl chloroformates results in decarboxylation of the mixed anhydride in situ, providing a route to mixed ethyl alkyl malonates in high yield under very mild conditions: Tetrahedron Lett., 26, 1573 (1985).
• The O,ɑ-dilithio-derivative, formed with n-BuLi in THF, can be acylated with acid chlorides to give, on acidic work-up (in situ decarboxylation), ?-ketoesters directly in high yield: J. Org. Chem., 44, 310 (1979); Org. Synth. Coll., 7, 213 (1990). Similarly, alkylation of the dilithio-derivative provides a direct route to esters of substituted acetic acids: J. Org. Chem., 40, 2556 (1975).