D97754

Diethyl malonate

ReagentPlus^®, 99%

• Synonym(s): Malonic acid diethyl ester
• Linear Formula: CH₂(COOC₂H₅)₂
• CAS Number: 105-53-3
• Molecular Weight: 160.17
• UNSPSC Code: 12352100
• NACRES: NA.22
• PubChem Substance ID: 24894329
• EC Number: 203-305-9
• Beilstein/REAXYS Number: 774687
• MDL number: MFCD00009195
• Assay: 99%
• Form: liquid

Properties

• vapor density: 5.52 (vs air)
• Quality Segment: 200
• vapor pressure: 1 mmHg ( 40 °C)
• product line: ReagentPlus^®
• assay: 99%
• form: liquid
• refractive index: n20/D 1.413 (lit.)
• bp: 199 °C (lit.)
• mp: −51-−50 °C (lit.)
• density: 1.055 g/mL at 25 °C (lit.)
• SMILES string: CCOC(=O)CC(=O)OCC
• InChI: 1S/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3
• InChI key: IYXGSMUGOJNHAZ-UHFFFAOYSA-N

Description

General description

Diethyl malonate is diethyl ester of malonic acid. It is widely used as a versatile building block for introducing the malonate functional group into molecules. Acylation of diethyl malonate using magnesium chloride and triethylamine is reported. K₂CO₃-catalyzed 1,4-addition reaction of diethyl malonate with various substituted 1,2-allenic ketones yields polyfunctionalized β,γ-unsaturated enones.

Application

Diethyl malonate was used to investigate Knoevenagel condensation reactions in microreactor using zeolite catalysts obtained by grafting amino groups onto NaX and CsNaX zeolites. It may be used in the synthesis of diethyl benzylidenemalonate by base catalyzed Knoevenagel condensation with benzaldehyde. It may be used in the synthesis of α-aryl malonates.

Packaging

Packaged in glass bottles

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H319
• pcodes: P264 - P280 - P305 + P351 + P338 - P337 + P313
• Hazard Classifications: Eye Irrit. 2
• Storage Class: 10 - Combustible liquids
• wgk: WGK 1
• flash_point_f: 199.4 °F - closed cup
• flash_point_c: 93 °C - closed cup
• ppe: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)