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Ethyl hydrogen malonate_Molecular_structure_CAS_1071-46-1)
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Ethyl hydrogen malonate

Catalog No. A12627 Name Alfa Aesar
CAS Number 1071-46-1 Website
M. F. C5H8O4 Telephone
M. W. 132.11462 Fax
Purity 96% Email
Storage Chembase ID: 123201

SYNONYMS

Title
丙二酸氢乙酯
IUPAC name
3-ethoxy-3-oxopropanoic acid
IUPAC Traditional name
ethyl hydrogen malonate
Synonyms
Malonic acid monoethyl ester
Monoethyl malonate

DATABASE IDS

Beilstein Number 1758845
EC Number 213-992-7
CAS Number 1071-46-1
MDL Number MFCD00020490

PROPERTIES

Purity 96%
Boiling Point 106°C/3mm
Density 1.119
Flash Point >110°C(230°F)
Refractive Index 1.4295
GHS Pictograms GHS07
GHS Hazard statements H315-H319-H335
European Hazard Symbols Irritant Irritant (Xi)
GHS Precautionary statements P261-P305+P351+P338-P302+P352-P321-P405-P501A
Risk Statements 36/37/38
Safety Statements 26-37-60
TSCA Listed

DETAILS

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).