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

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

Uses

Used in Pharmaceutical Industry:
Diethyl Diethylmalonate is used as an intermediate in the synthesis of Barbital (B118500), a prototype of the barbiturate hypnotics. Barbital is a sedative and hypnotic drug used to treat insomnia, anxiety, and seizures.
In addition to its use in the synthesis of Barbital, Diethyl Diethylmalonate may also be utilized in the production of other pharmaceuticals and chemicals, although specific applications are not provided in the given materials.

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

• 64-17-5 ethanol 
• 510-20-3 diethyl malonic acid 
• 60-29-7 diethyl ether 
• 996-82-7 sodium diethylmalonate 
• 75-03-6 ethyl iodide 
• 133-13-1 ethyl diethyl malonate 
• 105-53-3 diethyl malonate 
• 141-52-6 sodium ethanolate 
• 105-54-4 butanoic acid ethyl ester 
• 105-58-8 Diethyl carbonate 
• 75-00-3 chloroethane 
• 18995-13-6 Diethyl ethylsodiomalonate 
• 74-96-4 ethyl bromide 
• 67-56-1 methanol 

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.

COMPOUNDS AND USES

The invention relates to novel compounds (I), the use of compounds in eliciting a pro-Th17 immune response and related aspects. Further provided are methods of production of said compounds (I).

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 Monosubstituted Malonate Anions With Pyridinium and Quinolinium Salts

Monosubstituted malonate anions are alkylated at room temperature with 1-(sec-alkyl)quinolinium salts.Hindered disubstituted malonate esters can thus be prepared under very mild conditions.

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.

ASSIGNMENT OF THE DEUTERIUM QUADRUPOLAR SPLITTINGS FOR THE END-CHAIN OF 4-CYANO-4 prime -OCTYLBIPHENYL IN THE NEMATIC PHASE: A TEST BETWEEN THEORETICAL MODELS FOR END-CHAIN CONFORMATIONAL MOTION AND ORIENTATIONAL ORDERING.

4-Cyano-4 prime -(1,1,5,5-d//4-octyl)-biphenyl and 4-cyano-4 prime -(1,1,6,6-d//4-octyl)-biphenyl were synthesized and the deuterium quadrupole splittings measured for 4-octyl)-binphenyl nematic phases. The results, when combined with previous measurements on other specifically deuteriated derivatives enable a virtually complete assignment to be made of the quadrupolar splittings in the deuterium nmr spectrum of the perdeuteriated end-chain of this mesogen.