22398-14-7

Basic information

• Product Name: DIMETHYL METHOXYMETHYLENEMALONATE
• Synonyms: METHOXYMETHYLENEMALONIC ACID DIMETHYL ESTER;DIMETHYL METHOXYMETHYLENEMALONATE;MMMM;Dimethyl methoxymethylenemalonate, 98+%;Dimethylmethoxymethylenmalonat;Propanedioic acid, (methoxymethylene)-, dimethyl ester;2-methoxy-5,5-dimethyl-1,3-dioxane-4,6-dione;DiMethyl 2-(MethoxyMethylene)Malonate
• CAS NO: 22398-14-7
• Molecular Formula: C₇H₁₀O₅
• Molecular Weight: 174.15
• EINECS: 244-957-4
• Product Categories: fine chemicals
• Mol File: 22398-14-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 40-44 °C
• Boiling Point: 98 °C (0.5 mmHg)
• Flash Point: 158 °C
• Appearance: White/Crystalline Solid
• Density: 1.2311 (rough estimate)
• Vapor Pressure: 0.292mmHg at 25°C
• Refractive Index: 1.4390 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: DIMETHYL METHOXYMETHYLENEMALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL METHOXYMETHYLENEMALONATE(22398-14-7)
• EPA Substance Registry System: DIMETHYL METHOXYMETHYLENEMALONATE(22398-14-7)

Safety Data

• Hazard Codes: Xn
• Statements: 43-36/38-22
• Safety Statements: 37/39-26-24
• Hazardous Substances Data: 22398-14-7(Hazardous Substances Data)

Usage

Description

DIMETHYL METHOXYMETHYLENEMALONATE, also known as Dimethyl 2-(Methoxymethylene)malonate, is a white crystalline solid that serves as a valuable synthetic intermediate in the chemical industry. Its unique structure allows it to be utilized in the preparation of various compounds with significant applications.

Uses

Used in Pharmaceutical Industry:
DIMETHYL METHOXYMETHYLENEMALONATE is used as a synthetic intermediate for the preparation of (phenoxyethoxy)quinolones, which possess antimalarial activities. These quinolones are essential in the development of treatments for malaria, a widespread and potentially deadly disease.
Used in Medicinal Chemistry Research:
DIMETHYL METHOXYMETHYLENEMALONATE is used as a reagent in the synthesis of bicyclic pyridones. These compounds are prepared as oral selective CB2 agonists, which exhibit anti-pruritic activity. This application is crucial in the development of medications aimed at alleviating itching and other related discomforts.

InChI:InChI=1/C7H10O5/c1-10-4-5(6(8)11-2)7(9)12-3/h4H,1-3H3

Upstream product

• 99366-49-1 (4R,5S)-5-Dimethoxymethyl-4-methoxy-4,5-dihydro-pyrazole-3,3-dicarboxylic acid dimethyl ester 
• 27931-91-5 hydroxymethylenemalonic acid dimethyl ester 
• 104286-69-3 (R)-4-Methoxy-4,5-dihydro-pyrazole-3,3-dicarboxylic acid dimethyl ester 
• 108-59-8 malonic acid dimethyl ester 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 72179-89-6 2-benzyl-1,1,3-trioxo-1,2,3,6-tetrahydro-1λ⁶-[1,2,6]thiadiazine-4-carboxylic acid methyl ester 
• 18856-69-4 dimethyl (dimethylamino)methylidenemalonate 
• 125031-58-5 Methyl 1-(t-Butyl)-1,2-dihydro-5-methyl-2-oxo-3-pyridinecarboxylate 
• 125031-50-7 Methyl 1,2-Dihydro-6-(p-methoxyphenyl)-2-oxo-3-pyridinecarboxylate 
• 91586-27-5 6-(4-Methoxy-benzoyl)-2-oxo-5,6,7,8-tetrahydro-2H-pyrano[3,2-c]pyridine-3-carboxylic acid methyl ester 
• 125031-47-2 Methyl 1,2-Dihydro-2-oxo-6-phenyl-3-pyridinecarboxylate 
• 149742-99-4 methyl 1-(2,2-dimethoxyethyl)-2-(4-fluorophenyl)pyrimidin-6(1H)-one-5-carboxylate 
• 27931-91-5 hydroxymethylenemalonic acid dimethyl ester 
• 61559-23-7 dimethyl methoxymethylmalonate 
• 85531-80-2 methyl 2-oxo-2,5,6,7,8-pentahydro-2H-benzo[b]pyran-3-ylcarboxylate 
• 750647-64-4 2-[(2,3-diphenylquinoxalin-5-ylamino)methylene]malonic acid dimethyl ester 
• 462118-57-6 dimethyl benzoylaminomethylenemalonate 
• 104143-91-1 3-(6,7-Diphenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-2-carbomethoxypropionsaeuremethylester 
• 1233537-08-0 dimethyl 2-{[4-(4-trifluoromethylphenyl)thiazol-2-ylamino]methylene}malonate 

Relevant articles and documents

NMR spectroscopic data of some 1-alkoxy-2,2-di(carbonyl, carboxyl, cyano)-substituted ethylenes

The 1H-13C NMR shifts as well as 1H and 13C coupling constants of 14 alkoxymethylene malonic acid and acetoacetic acid derivatives and two alkoxymethylene acetylacetones are reported. The 17O NMR spectra have been recorded for six of them. The long-range coupling 3J(H-C=C-CR) has been used for determining the stereochemistry of the double bond. Copyright

Method for the preparation of alkoxymethylene compounds of acetic esters and substituted acetic esters

Disclosed is a method for preparation of alkoxymethylene compounds, especially methoxymethylene compounds, from substituted or unsubstituted acetic acid alkyl esters, especially methyl esters, from the corresponding hydroxymethylene compounds or their alkali salts, by reaction with excess alkanol, especially methanol, in the presence of HCl and a water-binding agent. Preferred are water-binding agents which form stable reaction products with water.

SYNTHESE ET REACTIVITE D'OXYCYCLOPROPANES ELECTROPHILES

"Electrophilic oxycyclopropanes" 4 to 6 have been prepared starting from olefins 7.Ring opening of these cyclopropanes occurs under very smooth conditions (DMSO, room temperature).A push-pull type system is then also a powerful driving force with regard to the C-C bond cleavage in cyclopropanes.