77-25-8

Basic information

• Product Name: DIETHYL DIETHYLMALONATE
• Synonyms: DIETHYLMALONIC ESTER;2,2-diethyl-malonicaciddiethylester;Diethyl 2,2-diethylmalonate;Diethyldiethylpropanedioate;Diethylmalonate diethyl ester;Diethylpropanedioicaciddiethylester;diethyl-propanedioicacidiethylester;Malonic acid, diethyl-, diethyl ester
• CAS NO: 77-25-8
• Molecular Formula: C₁₁H₂₀O₄
• Molecular Weight: 216.27
• EINECS: 201-016-2
• Product Categories: Pharmaceutical Intermediates;API intermediates
• Mol File: 77-25-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 228-230 °C(lit.)
• Flash Point: 202 °F
• Appearance: clear colorless liquid
• Density: 0.99 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0712mmHg at 25°C
• Refractive Index: n20/D 1.423(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Methanol (Sparingly)
• Merck: 14,3823
• CAS DataBase Reference: DIETHYL DIETHYLMALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL DIETHYLMALONATE(77-25-8)
• EPA Substance Registry System: DIETHYL DIETHYLMALONATE(77-25-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 77-25-8(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

Diethyl Diethylmalonate is an intermediate in the synthesis of Barbital (B118500), a prototype of the barbiturate hypnotics.

Synthesis Reference(s)

Journal of the American Chemical Society, 64, p. 578, 1942 DOI: 10.1021/ja01255a034

InChI:InChI=1/C11H20O4/c1-5-11(6-2,9(12)14-7-3)10(13)15-8-4/h5-8H2,1-4H3

Upstream product

• 67-56-1 methanol 
• 854842-99-2 ethyl-chloroethynyl-malonic acid diethyl ester 
• 74031-59-7 ethyl-(2-bromo-vinyl)-malonic acid diethyl ester 
• 49597-05-9 propene-1,1,3,3-tetracarboxylic acid tetraethyl ester 
• 75-03-6 ethyl iodide 
• 7647-01-0 hydrogenchloride 
• 93504-83-7 2-(ethoxycarbonyl)-2-ethylbutanoic acid 
• 510-20-3 diethyl malonic acid 
• 759-36-4 diethyl isopropylmalonate 
• 108-13-4 malonodiamide 
• 98129-24-9 2,4-bis-(bis-ethoxycarbonyl-methyl)-cyclobutane-1,1,3,3-tetracarboxylic acid tetraethyl ester 
• 74-96-4 ethyl bromide 
• 105-53-3 diethyl malonate 
• 64-67-5 diethyl sulfate 

Downstream Products

• 64289-52-7 acide diethyl-5,5 imino-2 barbiturique 
• 64289-52-7 2-amino-5,5-diethyl-1H-pyrimidine-4,6-dione 
• 57-44-3 diethylbarbituric acid 
• 3144-07-8 1,5,5-Triethylbarbitursaeure 
• 85432-35-5 5,5-diethyl-1-isopropylpyrimidinetrione 
• 51209-91-7 5,5-Diethyl-1-(2-methylpropyl)barbituric acid 
• 15517-31-4 5,5-diethyl-1-pentyl-barbituric acid 
• 5347-02-4 5,5-diethyl-2-anilino-1-phenyl-1H-pyrimidine-4,6-dione 
• 357-67-5 5,5-diethyl-1-phenylbarbituric acid 
• 92870-36-5 1-benzyl-5,5-diethyl-2,4,6(1H,3H,5H)pyrimidinetrione 
• 87215-95-0 5,5-diethyl-2-(4-chloro-anilino)-1H-pyrimidine-4,6-dione 
• 108718-35-0 5,5-diethyl-1-(2-chloro-benzyl)-2-thio-barbituric acid 
• 109092-27-5 5,5-diethyl-1-(1-phenyl-ethyl)-barbituric acid 

Relevant articles and documents

Method for preparing diethyl malonate

The invention relates to a novel method for preparing diethyl malonate, comprisign the following steps: using malonate as a raw material, sodium hydride as a catalyst and diethyl sulfate as an ethylation reagent, stirring at 70-100 DEG C to react for 3-5 hours, and carrying out after-treatment on the reaction solution after the reaction is finished. The method is low in cost, easy in reaction operation and high in yield.

Copper(II)-catalyzed enantioselective intramolecular cyclization of N-alkenylureas

The first Cu(II)-catalyzed highly enantioselective intramolecular cyclization of N-alkenylureas was developed for the concise assembly of chiral vicinal diamino bicyclic heterocycles. Facile removal of carbonyl group of the carbamido moiety allowed for ready access to enantioenriched cyclic vicinal diamines.

ALKYLATION OF MALONIC ESTER AND MONOALKYLMALONIC ESTERS UNDER THE CONDITIONS OF PHASE-TRANSFER CATALYSIS

Simple procedures were developed for the monoalkylation of malonic ester in the potassium hydroxide-DMFA (DMFA-acetone)-triethylbenzylammonium chloride system and the alkylation of alkylmalonic esters to dialkylmalonic esters in the calcium oxide-DMFA system.