CAS 1071-46-1|3-ethoxy-3-oxopropanoic acid|ethyl hydrogen malonate|3-ethoxy-3-oxopropanoic acid|Monoethyl hydrogen malonate|丙二酸单乙酯|3-Ethoxy-3-oxopropanoic acid|mono-Ethyl malonate|(Ethoxycarbo...

General Information

Structure

Molecular Formula

C₅H₈O₄

Molecular Mass

132.11462

Exact Mass

132.04225874

Charge

InChI

InChI=1S/C5H8O4/c1-2-9-5(8)3-4(6)7/h2-3H2,1H3,(H,6,7)

InChIKey

HGINADPHJQTSKN-UHFFFAOYSA-N

Canonic Smiles

CCOC(=O)CC(=O)O

Isomeric Smiles

C(C(=O)O)C(=O)OCC

Calculated Properties

JChem

Acid pKa

3.917031

H Acceptors

H Donor

LogD (pH = 5.5)

-1.4176992

LogD (pH = 7.4)

-3.0331244

Log P

0.17158474

Molar Refractivity

28.5055

Polarizability

11.39605

Polar Surface Area

63.6

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC name

3-ethoxy-3-oxopropanoic acid

IUPAC Traditional name

ethyl hydrogen malonate

Synonyms

3-ethoxy-3-oxopropanoic acidMonoethyl hydrogen malonate丙二酸单乙酯3-Ethoxy-3-oxopropanoic acidmono-Ethyl malonate(Ethoxycarbonyl)acetic acidMonoethyl malonateEthyl hydrogen malonateMonoethyl malonateMalonic acid monoethyl ester丙二酸氢乙酯Ethyl malonateEthyl hydrogen malonateETHYL HYDROGEN MALONATE

Names and Identifiers

Registration numbers

CAS Number

PubChem SID

EC Number

MDL Number

Beilstein Number

PubChem CID

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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.

Molecule Details

References

PubChem Literature

From Data Sources

• 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).

• 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).

• 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).

• 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).

• See also Ethyl potassium malonate, A10720.

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

3-ethoxy-3-oxopropanoic acid

IUPAC Traditional name

ethyl hydrogen malonate

Synonyms

Registration numbers

CAS Number

PubChem SID

EC Number

MDL Number

Beilstein Number

PubChem CID

Molecule Details

445088

References

PubChem Literature

From Data Sources

• 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).

• 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.

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:123201