Diethyl ethoxymethylenemalonate

• Catalog No.: A13776
• CAS Number: 87-13-8
• M. F.: C10H16O5
• M. W.: 216.23104
• Purity: 98+%

SYNONYMS

• Title: 乙氧亚甲基丙二酸二乙酯
• IUPAC name: 1,3-diethyl 2-(ethoxymethylidene)propanedioate
• IUPAC Traditional name: 1,3-diethyl 2-(ethoxymethylidene)propanedioate
• Synonyms: Ethoxymethylenepropanedioic acid diethyl ester; Ethoxymethylenemalonic acid diethyl ester

DATABASE IDS

• MDL Number: MFCD00009148
• CAS Number: 87-13-8
• EC Number: 201-725-7
• Beilstein Number: 880058

PROPERTIES

• Purity: 98+%
• Boiling Point: 136-139°C/10mm
• Density: 1.080
• Flash Point: 144°C(291°F)
• Melting Point: -33°C
• Refractive Index: 1.4620
• GHS Hazard statements: H334-H315-H319-H317-H303
• European Hazard Symbols: X
• GHS Precautionary statements: P285-P261-P305+P351+P338-P302+P352-P321-P501A
• Risk Statements: 22-36/38-42/43
• RTECS: OO1100000
• Safety Statements: 23-24-26-36/37-45
• TSCA Listed: 是

REFERENCES

• Can be converted to the unstable diethyl methylenemalonate by catalytic reduction and elimination of ethanol on distillation, see: Org. Synth. Coll., 4, 298 (1963).
• Stable equivalent of the ɑ-formylmalonate, valuable synthetic building block, particularly in heterocyclic syntheses. Review: Adv. Het. Chem., 54, (1992).
• Has been used for the protection of the amino group of ɑ-amino acids, allowing clean esterification by O-alkylation. The protecting group can be removed using bromine in chloroform: Synthesis, 544 (1989):
  
• For N-protection of aminoglycosides prior to O-acetylation, see: J. Carbohydr. Chem., 14, 1133 (1995). Chlorine in chloroform at 0^oC was used for deprotection.