Dimethyl methoxymethylenemalonate Property

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

Hazard Codes 

Xn

Risk Statements 

43-36/38-22

Safety Statements 

37/39-26-24

HS Code 

29171990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P284Wear respiratory protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

Dimethyl methoxymethylenemalonate Chemical Properties,Usage,Production

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.