Diethyl malonate

• Catalog No.: A15468
• CAS Number: 105-53-3
• M. F.: C7H12O4
• M. W.: 160.16778
• Purity: 99%

SYNONYMS

• Title: 丙二酸二乙酯
• IUPAC name: 1,3-diethyl propanedioate
• IUPAC Traditional name: diethyl malonate
• Synonyms: Malonic acid diethyl ester; Propanedioic acid diethyl ester

DATABASE IDS

• EC Number: 203-305-9
• MDL Number: MFCD00009195
• Merck Index: 143823
• CAS Number: 105-53-3
• Beilstein Number: 774687

PROPERTIES

• Purity: 99%
• Boiling Point: 198-200°C
• Density: 1.055
• Flash Point: 90°C(194°F)
• Melting Point: -50°C
• Refractive Index: 1.4140
• GHS Hazard statements: H227
• RTECS: OO0700000
• TSCA Listed: 是

REFERENCES

• 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).
• 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:
  
• 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.
• Compare also Dimethyl malonate, A11007, Di-tert-butyl malonate, A12774, Dibenzyl malonate, A10844, and Isopropylidene malonate, A15603.
• Substituents can also be introduced by Michael addition; see e.g.: Org. Synth. Coll., 8, 467 (1993).
• Arylation occurs with aryl bromides in the presence of CuI: Gazz. Chim. Ital., 122, 511 (1992).