Ethyl hydrogen malonate

Details:

Melting point     -13°C(lit.)
Boiling point     106.5 °C/3 mmHg (lit.)
density     1.119 g/mL at 25 °C (lit.)
refractive index     n20/D 1.435(lit.)
Fp     >230 °F
storage temp.     Sealed in dry,Room Temperature
pka    pK1:3.55 (25°C)
form     Liquid
color     Pale yellow
Water Solubility     Miscible with water, chloroform and other solvents.
BRN     1758845
InChIKey    HGINADPHJQTSKN-UHFFFAOYSA-N
CAS DataBase Reference    1071-46-1(CAS DataBase Reference)
Safety Information
Hazard Codes     Xi
Risk Statements     36/37/38
Safety Statements     26-36
WGK Germany     3
HS Code     29171900

Chemical Properties    Yellow liquid
Uses    Ethyl Hydrogen Malonate has been shown to impair brain mitochondrial succinate and malate transport. It is also found in the extract of Hericum erinaceus mushroom which shows antitumor effects in tumo r-bearing mice.
Uses    Ethyl hydrogen malonate is used as a reactant for the preparation of tetramic acids through Dieckmann ring closure and organocatalytic decarboxylative Doebner-Knoevenagel reactions. It is involved in the acylation reactions and Knoevenagel condensation with aldehydes. It is also used in the preparation of gamma-lactones from olefins by intermolecular carbolactonization in presence of Mn(III) acetate as a catalyst.
Synthesis Reference(s)    Organic Syntheses, Coll. Vol. 4, p. 417, 1963
Tetrahedron Letters, 26, p. 1411, 1985 DOI: 10.1016/S0040-4039(00)99058-0