Substance
ID:717756
Names and Identifiers
IUPAC name
1,3-diethyl propanedioate
IUPAC Traditional name
diethyl malonate
Synonyms
丙二酸二乙酯Malonic acid diethyl esterDiethyl malonatePropanedioic acid diethyl ester
Registration numbers
Beilstein Number
EC Number
CAS Number
Merck Index
MDL Number
Properties
Product Information
Purity
99%
Physical Property
Boiling Point
198-200°C
Refractive Index
1.4140
Melting Point
-50°C
Density
1.055
Flash Point
90°C(194°F)
Safety Information
GHS Hazard statements
H227
RTECS
OO0700000
TSCA Listed
是
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• Arylation occurs with aryl bromides in the presence of CuI: Gazz. Chim. Ital., 122, 511 (1992).
• Compare also Dimethyl malonate, A11007, Di-tert-butyl malonate, A12774, Dibenzyl malonate, A10844, and Isopropylidene malonate, A15603.
• For phase-transfer monoalkylation of the active methylene group see, e.g. (18-crown-6): Synthesis, 37 (1977); and (BTEAC): Org. Prep. Proced. Int., 26, 469 (1994). Solid-liquid phase transfer alkylation has been promoted by microwave irradiation: Synth. Commun., 25,1761 (1995). Dialkylation can also occur in the presence of BTEAC: Synthesis, 54 (1985); Org. Synth. Coll., 7, 411 (1990), to give cyclopropane derivatives. Stereoselective alkylation has been achieved under particularly mild conditions with secondary alkyl mesylates in the presence of Cesium fluoride, 12885 in DMF; complete inversion occurs at the secondary alkyl carbon: J. Org. Chem., 60, 2627 (1995); see also: Synlett, 499 (1998).
• Substituents can also be introduced by Michael addition; see e.g.: Org. Synth. Coll., 8, 467 (1993).
• A number of procedures have been devised for the direct conversion of malonic esters to acetic esters (decarboalkoxylation), in a single step of which heating in wet DMSO is perhaps the simplest: J. Org. Chem., 43, 138 (1978). See also 1,4-Diazabicyclo[2.2.2]octane, A14003.
• C-Acylation of malonic esters is normally carried out by reaction of the Mg derivative with an acid chloride. A convenient method using a combination of MgCl2 and triethylamine was introduced by Rathke: J. Org. Chem., 50, 2622 (1985); see also Triethylamine, A12646 for discussion of this system:
