| Identification | More | [Name]
DIMETHYL METHOXYMETHYLENEMALONATE | [CAS]
22398-14-7 | [Synonyms]
DIMETHYL METHOXYMETHYLENEMALONATE
METHOXYMETHYLENEMALONIC ACID DIMETHYL ESTER
MMMM
Dimethyl methoxymethylenemalonate, 98+%
Dimethylmethoxymethylenmalonat | [EINECS(EC#)]
244-957-4 | [Molecular Formula]
C7H10O5 | [MDL Number]
MFCD00038225 | [Molecular Weight]
174.15 | [MOL File]
22398-14-7.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystalline solid | [Melting point ]
40-44 °C | [Boiling point ]
98 °C (0.5 mmHg) | [density ]
1.2311 (rough estimate) | [refractive index ]
1.4390 (estimate) | [Fp ]
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) |
| Hazard Information | Back Directory | [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.
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