Dimethyl methoxymethylenemalonate Chemical Properties

Melting point:

40-44 °C

Boiling point:

98 °C (0.5 mmHg)

Density 

1.2311 (rough estimate)

refractive index 

1.4390 (estimate)

Flash point:

158 °C

storage temp. 

Sealed in dry,Room Temperature

form 

Crystalline Solid

color 

White

InChI

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

InChIKey

RHFZTBSULNJWEI-UHFFFAOYSA-N

SMILES

C(OC)(=O)/C(=C\OC)/C(OC)=O

CAS DataBase Reference

22398-14-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

43-36/38-22

Safety Statements 

37/39-26-24

HS Code 

29171990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

Dimethyl methoxymethylenemalonate Usage And Synthesis

Chemical Properties

white crystalline solid

Uses

Dimethyl 2-(Methoxymethylene)malonate is a useful synthetic intermediate. It is used in preparation of (phenoxyethoxy)quinolones with antimalarial activities. It is also a reagent used in the synthesis of bicyclic pyridones prepn. as oral selective CB2 agonists with anti-pruritic activity.

Synthesis

264.2 g (2.0 mol) of dimethyl malonate, 637 g (6 mol) of trimethyl orthoformate and 20.4 g (0.2 mol) of acetic anhydride containing 2 g of H2 SO4 -activated bentonite were initially introduced into a reaction flask provided with a stirrer, thermometer, dropping funnel, column and reflux condensor, and the mixture was heated to boiling. 40.8 g (0.4 mol) of acetic anhydride was continuously metered for6 hours. The low boiling component formed was distilled off at a head temperature of 62° to 67° C. The bottom temperature increased slowly from 109° to 133° C. After 8 hours; the excess orthoester was distilled off at reduced pressure. 40.8 g (0.4 mol) of acetic anhydride was added to the remaining reaction mixture, and the mixture was heated at 140° C. for 2 hours. The catalyst was filtered off, and the crude product was distilled in vacuo. 330.4 g of dimethyl methoxymethylenemalonate (98% pure), having a melting point of 44° to 46° C., were obtained at 0.5 mbar and a head temperature of 110° C.

Dimethyl methoxymethylenemalonate(22398-14-7)Related Product Information

• isopropyl 2-Methoxyacetate
• (Z)-2-Methoxyimino-2-(furyl-2-yl) acetic acid ammonium salt
• Methyl (triphenylphosphoranylidene)acetate
• (Carbomethoxymethyl)triphenylphosphonium bromide
• Methoxyammonium chloride
• DIMETHYL METHOXYMALONATE
• Dibutyl maleate
• Dimethyl methylmalonate
• Dimethyl malonate
• DIMETHYL METHOXYMETHYLENEMALONATE ((MMMM)
• DIMETHYL METHOXYMETHYLENEMALONATE
• SALOR-INT L305529-1EA
• Diethyl ethoxymethylenemalonate