[A12627] CAS 1071-46-1 | Ethyl hydrogen malonate, 96%

CAS : 1071-46-1
MDL : MFCD00020490
EINECS : 213-992-7

Other name :

Malonic acid monoethyl esterMonoethyl malonate

Chemical Properties

Formula : C5H8O4
Formula weight : 132.12
Boiling Point : 106°/3mm
Flash point : >110°(230°F)
Density : 1.119
Refractive Index : 1.4295
Sensitivity : Keep Cold.
Form : Liquid
Solubility : Miscible with water, chloroform and other solvents.

Literature References

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). Half esters of malonic acid react with ɑß-enals in pyridine/ DMAP to give ɑß δ-dienoic esters with good (E)-selectivity: Synthesis: 534 (1988). 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), ß-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). 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.

Notes

Incompatible with strong oxidizing agents.Other References:Beilstein: 1758845

Grade Specifications

Grade Specifications

Hazard Statements : H315-H319-H335Causes skin irritation.Causes serious eye irritation.May cause respiratory irritation.
Precautionary Statements : P261-P305+P351+P338-P302+P352-P321-P405-P501aAvoid breathing dust/fume/gas/mist/vapours/spray.IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.IF ON SKIN: Wash with plenty of soap and water.Specific treatment (see label).Store locked up.Dispose of contents/container in accordance with local/regional/national/international regulations.