53704-09-9

Basic information

• Product Name: DIMETHYL 2-AMINOMALONATE, TECH
• Synonyms: DIMETHYL 2-AMINOMALONATE, TECH;DIMETHYLAMINOMALONATE;Propanedioic acid, 2-aMino-, 1,3-diMethyl ester;Dimethyl 2-aminopropanedioate
• CAS NO: 53704-09-9
• Molecular Formula: C₅H₉NO₄
• Molecular Weight: 147.12926
• Product Categories: Aliphatics;Esters
• Mol File: 53704-09-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 155.7 °C at 760 mmHg
• Flash Point: 33.2 °C
• Appearance: /
• Density: 1.205 g/cm³
• Storage Temp.: 2-8°C
• PKA: 15.30±0.59(Predicted)
• CAS DataBase Reference: DIMETHYL 2-AMINOMALONATE, TECH(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL 2-AMINOMALONATE, TECH(53704-09-9)
• EPA Substance Registry System: DIMETHYL 2-AMINOMALONATE, TECH(53704-09-9)

Safety Data

• Hazardous Substances Data: 53704-09-9(Hazardous Substances Data)

Usage

General Description

DIMETHYL 2-AMINOMALONATE, TECH is a chemical compound often used in the synthesis of pyrazolopyridines, a class of molecules with potential applications in the pharmaceutical industry. It is an intermediate in the manufacturing of numerous pharmaceutical compounds. This organic compound is a clear, colorless liquid with a faint odor and is highly soluble in water. It is also known for its ability to form strong hydrogen bonds with water molecules, making it useful in various chemical reactions and as a building block for the synthesis of more complex molecules. Additionally, this chemical compound is known to have low toxicity and is considered safe when handled and used according to proper safety guidelines.

InChI:InChI=1S/C5H9NO4/c1-9-4(7)3(6)5(8)10-2/h3H,6H2,1-2H3

Upstream product

• 108-59-8 malonic acid dimethyl ester 
• 27160-23-2 dimethyl formamidomalonate 
• 42937-74-6 dimethyl 2-(hydroxyimino)malonate 

Downstream Products

• 796875-13-3 dimethyl [(2,4-dichlorobenzoyl)amino]malonate 

Relevant articles and documents

Total synthesis of tryprostatins A and B

Three distinct synthetic routes to the 2-prenyl tryptophan core skeleton of tryprostatins and their total syntheses are described. The strategies include a traditional gramine-mediated coupling reaction, Fuerstner indole synthesis, and our radical-mediated indole synthesis from o-alkenylphenyl isocyanide. The establishment of reliable conditions for the radical-mediated construction of indoles via a low-temperature radical initiator V-70 (2,2′-azobis(4- methoxy-2,4-dimethylvaleronitrile)) led to the highly efficient syntheses of tryprostatins A and B.

Porphyrins with Exocyclic Rings. 2. Synthesis of Geochemically Significant Tetrahydrobenzoporphyrins from 4,5,6,7-Tetrahydro-2H-isoindoles

Benzo- and tetrahydrobenzoporphyrins are widespread constituents of oil shales and petroleum.Although the origins of these materials are not known, a case is made for divinylchlorophyll a, a widespread pigment in marine algae, being the precursor to many of these geoporphyrins.Total syntheses of four tetrahydrobenzoporphyrins related to etioporphyrin III are described.Tetrahydroisoindoles were prepared by condensation of isocyanoacetates with 1-nitrocyclohexene in the presence of DBU or by reaction of aminomalonates with 2-formylcyclohexanone.Condensation of 3-unsubstituted 4,5,6,7-tetrahydro-2H-isoindoles 23c and 23d with (acetoxymethyl)pyrroles in the presence of Montmorillonite clay gave dipyrrylmethanes 28a and 36a in excellent yield.Hydrogenolysis of the benzyl esters and subsequent acid-catalyzed condensation with pyrrole aldehydes 37a and /or 37b gave a series of a,c-biladiene dihydrobromides.Copper(II) mediated cyclization of the a,c-biladienes 32, 33, 35, and 38, followed by demetallation with 15percent sulfuric acid-trifluoroacetic acid, gave four isomeric tetrahydrobenzoporphyrins 10-13 in unusually high yield.This work provides a general route for the synthesis of these important porphyrin molecular fossils.

Reagents for Bioorganic Synthesis. 2. Methyl N-(Dicarboxymethyl)methanimidate

Preparation, properties, and reactions of the reagent methyl N-(dicarbomethoxymethyl)methanimidate (1) are reported.Dropwise addition of dimethyl aminomalonate to refluxing trimethyl orthoformate/TFA afforded 1.Treatment of 1 with ammonia and various primary amines gave the corresponding unsubstituted and 1-substituted 4-carbomethoxy-5-hydroxyimidazoles 7-12, either as the parent hydroxy compounds (a) or as the (alkyl)ammonium salts (b).The reaction of 1 with water and sodium hydrosulfide provided dimethyl N-formylaminomalonate (13) and dimethyl N-(thioformyl)aminomalonate (14), respectively.The reaction of 1 with excess sodium hydrosulfide resulted in the formation of methyl N-(thioformyl)aminoacetate (17).Conversions of methylammonium 4-carbomethoxy-1-methylimidazol-5-olate (8b) and benzylammonium 4-carbomethoxy-1-benzylimidazol-5-olate (9b) into 5-(benzylamino)-4-(benzylcarbamoyl)-1-methylimidazole (18) and 1-benzyl-5-(benzylamino)-4-(benzylcarbamoyl)imidazole (19), respectively, were each accomplished in a single-pot procedure, employing phenylphosphonic dichloride as the key reagent.