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1071-46-1 molecular structure
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3-ethoxy-3-oxopropanoic acid

ChemBase ID: 123201
Molecular Formular: C5H8O4
Molecular Mass: 132.11462
Monoisotopic Mass: 132.04225874
SMILES and InChIs

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

Cite this record

CBID:123201 http://www.chembase.cn/molecule-123201.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
1071-46-1
EC Number
213-992-7
MDL Number
MFCD00020490
Beilstein Number
1758845
PubChem SID
24868159
162217554
PubChem CID
70615

CALCULATED PROPERTIES

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 cm3 Polarizability 11.39605 Å3
Polar Surface Area 63.6 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Apperance
Liquid expand Show data source
Melting Point
200 - 202°C expand Show data source
Boiling Point
106.5 °C/3 mmHg(lit.) expand Show data source
106°C/3mm expand Show data source
Flash Point
>110°C(230°F) expand Show data source
113 °C expand Show data source
235.4 °F expand Show data source
Density
1.119 expand Show data source
1.119 g/mL at 25 °C(lit.) expand Show data source
Refractive Index
1.4295 expand Show data source
n20/D 1.435(lit.) expand Show data source
Hydrophobicity(logP)
0.352 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
26-37-60 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
Purity
90+% expand Show data source
95% expand Show data source
96% expand Show data source
98% expand Show data source
Impurities
<10% ethyl malonate, potassium salt expand Show data source
Linear Formula
HO2CCH2CO2C2H5 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 445088 external link
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

REFERENCES

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  • • 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).
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PATENTS

PATENTS

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INTERNET

INTERNET

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