Ethyl hydrogen malonate

• Catalog No.: A12627
• CAS Number: 1071-46-1
• M. F.: C5H8O4
• M. W.: 132.11462
• Purity: 96%

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 Hazard statements: H315-H319-H335
• European Hazard Symbols: 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: 否

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).