6829-40-9

Basic information

• Product Name: 2-AMINODIETHYLMALONATE
• Synonyms: AMINOMALONIC ACID DIETHYL ESTER;2-AMINODIETHYLMALONATE;DIETHYL AMINOMALONATE;Aminopropanedioicaciddiethylester;Ethylaminomalonate;DIETHYL AMINOMALINATE;2-Aminomalonic acid diethyl;2-Aminomalonic acid diethyl ester
• CAS NO: 6829-40-9
• Molecular Formula: C₇H₁₃NO₄
• Molecular Weight: 175.18
• EINECS: 229-905-0
• Product Categories: Pharmaceutical Intermediates;straight chain compounds;Amines;Intermediates
• Mol File: 6829-40-9.mol

Chemical Properties

• Melting Point: 170 °C
• Boiling Point: 306.47°C (rough estimate)
• Flash Point: 52.3 °C
• Appearance: Colourless oil
• Density: 1.1000
• Refractive Index: 1.4353 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 15.34±0.59(Predicted)
• CAS DataBase Reference: 2-AMINODIETHYLMALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINODIETHYLMALONATE(6829-40-9)
• EPA Substance Registry System: 2-AMINODIETHYLMALONATE(6829-40-9)

Safety Data

• Hazardous Substances Data: 6829-40-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINODIETHYLMALONATE is used as a reagent for the synthesis of imidazole derivatives, which are essential in the development of various pharmaceutical compounds. Imidazole derivatives have been found to possess a range of biological activities, including antifungal, antibacterial, antiviral, and anti-inflammatory properties. They are also used in the treatment of conditions such as hypertension, asthma, and allergies.
Used in Chemical Synthesis:
2-AMINODIETHYLMALONATE is used as a key intermediate in the synthesis of various organic compounds, particularly those containing the imidazole ring structure. This versatile reagent is employed in the production of a wide range of chemicals, including pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Research and Development:
2-AMINODIETHYLMALONATE is utilized as a valuable research tool in the development of new chemical entities and the study of their properties. Its role in the synthesis of imidazole derivatives makes it an essential component in the exploration of novel compounds with potential applications in various fields, such as medicine, agriculture, and materials science.

InChI:InChI=1/C7H14NO4/c1-3-7(8,4-2,5(9)10)6(11)12/h3-4,8H2,1-2H3,(H,9,10)(H,11,12)/p-2

Upstream product

• 6829-41-0 diethyl oximinomalonate 
• 603-67-8 diethyl nitromalonate 
• 105-53-3 diethyl malonate 
• 1068-90-2 2-acetylaminomalonic acid diethyl ester 
• 6326-44-9 diethyl 2-formylaminomalonate 
• 13433-00-6 diethyl aminomalonate hydrochloride 
• 7338-94-5 1,3-diphenyl-2-propynone 
• 996-82-7 sodium diethylmalonate 
• 64-17-5 ethanol 
• 91469-69-1 ethylesters of amino malonic acid 
• 168207-98-5 diethyl 2,2-diazidomalonate 

Downstream Products

• 114282-94-9 (benzylsulfanylthiocarbonyl-amino)-malonic acid diethyl ester 
• 14769-29-0 diethyl 2-[[2-(benzyloxycarbonylamino)acetyl]amino]propanedioate 
• 500791-38-8 (2-phenyl-thioacetylamino)-malonic acid diethyl ester 
• 21024-83-9 Cbo-L-alanyl-aminomalonsaeurediethylester 
• 32683-00-4 ethyl 2-phenylimidazole-4-carboxylate 
• 62009-47-6 2-aminopropanediamide 
• 56-40-6 glycine 
• 617-45-8 aspartic Acid 
• 142-73-4 iminodiacetic acid 
• 609-36-9 rac-Pro-OH 
• 1068-90-2 2-acetylaminomalonic acid diethyl ester 
• 96-86-6 diethyl benzamidomalonate 
• 54001-50-2 2-(3-phenylureido)malonic acid diethyl ester 
• 129221-15-4 2-(4-nitrobenzoylamino)propanedioic acid diethyl ester 

Relevant articles and documents

Regiochemistry in 1,3-dipolar cycloadditions of the azomethine ylide formed from diethyl aminomalonate and paraformaldehyde

The azomethine ylide derived from the condensation of diethyl aminomalonate with paraformaldehyde undergoes 1,3-dipolar cycloadditions with acrylate and propiolate derivatives. Contrary to a previous report, these reactions yield mixtures of regioisomers

Scalable synthesis of favipiravir: Via conventional and continuous flow chemistry

Decagram scale synthesis of favipiravir was performed in 9 steps using diethyl malonate as cheap starting material. Hydrogenation and bromination steps were achieved by employing a continuous flow reactor. The synthetic process provided a total of 16% yield and it is suitable for larger-scale synthesis and production. This journal is

Preparation method of diethyl amino-malonate hydrochloride

The preparation method comprises first steps of preparing diethyl malonate in acetic acid, subnitration with an aqueous solution of nitrous acid to obtain the oxime-based malonic acid diethyl ester. 2nd: The oxime-based malonate is subjected to catalytic hydrogenation reaction with a nickel-containing ternary catalyst in an alcohol solvent to obtain diethyl amino-malonate. 3rd-Step: After the catalyst is filtered off, the catalyst is salified with hydrogen chloride ethanol and then dissolved in acetone to obtain diethyl amino-malonate hydrochloride. The method has the characteristics of mild and safe reaction conditions, simple and convenient operation, high yield, low cost, good quality and the like, and has wide application prospects. In addition, the hydrogenation technology for the method not only avoids waste residues and waste acid generated by reduction of zinc powder, but also avoids the disadvantages of expensive price and easy poisoning inactivation of the palladium-carbon catalyst.

A TRANSITION METAL COMPLEX COMPOUND

The present invention relates to a transition metal complex (Z) (described herein), which is stable and can be effectively used as a catalyst in various chemical transformations such as to prepare chemical intermediates, agrochemical compounds as well as pharmaceutical compounds.

AN IMPROVED HYDROGENATION PROCESS USING A TRANSITION METAL COMPLEX CATALYST

The present invention relates to the process of reduction of compound of formula (II) by using a transition metal complex (Z) as a catalyst for hydrogenation reactions to get compound of formula (I). More particularly, the present invention relates to an improved process for the preparation of a compound (I) (as described herein) or a salt thereof; comprising hydrogenation of the compound (II) (as described herein) using a transition metal complex catalyst (Z).

Diversity-oriented synthesis of chromenopyrrolidines from azomethine ylides and 2-hydroxybenzylidene indandiones via base-controlled regiodivergent (3+2) cycloaddition

An organobase-directed, regiodivergent 1,3-dipolar cycloaddition of azomethine ylides and 2-hydoxybenzylidene indandiones is reported. The scarcely explored reversal of the nucleophilic site in azomethine ylides has been exploited for their regiodivergent (3+2) cycloaddition, which subsequently resulted in two different cascade processes to generate functionally distinct chromenopyrrolidines in a diversity oriented manner.

Umpolung of o-Hydroxyaryl Azomethine Ylides: Entry to Functionalized ?-Aminobutyric Acid under Phosphine Catalysis

A phosphine-catalyzed reaction between o-hydroxyaryl azomethine ylides and MBH carbonates provides access to highly functionalized ?-aminobutyric acid derivatives in moderate to good yields. Mechanistically, the reaction involves a phosphine-catalyzed tandem SN2′/2-aza-Cope rearrangement/intramolecular addition process.

Organocatalytic Regiodivergent C?C Bond Cleavage of Cyclopropenones: A Highly Efficient Cascade Approach to Enantiopure Heterocyclic Frameworks

Here a highly efficient cascade approach is reported that combines a cycloaddition reaction with a regioselective strain-release process to afford diverse heterocyclic frameworks through bifunctional catalysis. The cooperation of hydrogen-bonding network activation and a regiodivergent strain-assisted effect is the key to promoting this complex chemical transformation, leading to the generation of two different ring systems in high yields with excellent stereoselectivities. The reaction proceeded by a mechanism involving a “spring-loaded” intermediate with switchable C?C bond cleavages achieved by controllable ring-strain release. This reaction was also amenable to gram scale synthesis with only 0.1 mol % catalyst loading.

Hydrogenolysis of geminal diazides

The complete hydrogenolysis of compounds containing the geminal diazido functionality is described. Using hydrogen over palladium on charcoal, the diazides are reduced, and primary amines are obtained. For example, aminomalonates and glycines are generated in a straightforward manner. A protocol that provides direct access to acetylated amines derived from 2-amino-1,3-diketones in good to excellent yields, via hydrogenation in the presence of acetic anhydride, is also presented.

An enantioselective cascade for simultaneous generation of five quaternary stereocenters from fully substituted enones

A highly enantioselective cascade reaction for the generation of five quaternary stereocenters in one-pot operation is reported for the first time in the history of organic synthesis. Cinchona-alkaloid derived hydrogen-bonding catalyst furnished structurally complex cascade products from simple substrates in excellent yields and stereoselectivities.