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Diethyl ethoxymethylenemalonate, 98+%, Thermo Scientific Chemicals
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Catalog number A13776.22
also known as A13776-22
Price (USD)/ Each
37.10
-
Quantity:
100 g
Price (USD)/ Each
37.10
Diethyl ethoxymethylenemalonate, 98+%, Thermo Scientific Chemicals
Catalog numberA13776.22
Price (USD)/ Each
37.10
-
Chemical Identifiers
CAS87-13-8
IUPAC Name1,3-diethyl 2-(ethoxymethylidene)propanedioate
Molecular FormulaC10H16O5
InChI KeyLTMHNWPUDSTBKD-UHFFFAOYSA-N
SMILESCCOC=C(C(=O)OCC)C(=O)OCC
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Specifications
Specification Sheet
Specification SheetIdentification (FTIR)Conforms
Appearance (Color)Clear colorless
Assay (GC)≥98.0%
Refractive Index1.4605-1.4645 @ 20?C
FormLiquid
Diethyl ethoxymethylenemalonate is used for synthesis of pyrido[3,2-e]pyrimido[1,2-c]pyrimidines. Initially, it was used to monitor lysine decarboxylase activity. It is useful in the determination of amino acids by precolumn derivatization by using reversed-phase high-performance liquid chromatography (HPLC). It plays an important role in the Gould-Jacobs reaction to prepare quinolines. For example, anile reacts with this reagent to give 4-hydroxyquinoline. It acts as an intermediate in the production of flumequine, which is a fluoroquinolone antibiotic.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
Diethyl ethoxymethylenemalonate is used for synthesis of pyrido[3,2-e]pyrimido[1,2-c]pyrimidines. Initially, it was used to monitor lysine decarboxylase activity. It is useful in the determination of amino acids by precolumn derivatization by using reversed-phase high-performance liquid chromatography (HPLC). It plays an important role in the Gould-Jacobs reaction to prepare quinolines. For example, anile reacts with this reagent to give 4-hydroxyquinoline. It acts as an intermediate in the production of flumequine, which is a fluoroquinolone antibiotic.
Solubility
Miscible with chloroform, dichloromethane and methanol. Immiscible with water.
Notes
Incompatible with acids, bases, oxidizing agents and reducing agents.
Diethyl ethoxymethylenemalonate is used for synthesis of pyrido[3,2-e]pyrimido[1,2-c]pyrimidines. Initially, it was used to monitor lysine decarboxylase activity. It is useful in the determination of amino acids by precolumn derivatization by using reversed-phase high-performance liquid chromatography (HPLC). It plays an important role in the Gould-Jacobs reaction to prepare quinolines. For example, anile reacts with this reagent to give 4-hydroxyquinoline. It acts as an intermediate in the production of flumequine, which is a fluoroquinolone antibiotic.
Solubility
Miscible with chloroform, dichloromethane and methanol. Immiscible with water.
Notes
Incompatible with acids, bases, oxidizing agents and reducing agents.
RUO – Research Use Only
General References:
- Stable equivalent of the ɑ-formylmalonate, valuable synthetic building block, particularly in heterocyclic syntheses. Review: Adv. Het. Chem., 54, (1992).
- Can be converted to the unstable diethyl methylenemalonate by catalytic reduction and elimination of ethanol on distillation, see: Org. Synth. Coll., 4, 298 (1963).
- 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°C was used for deprotection.
- Kim, Y. H.; Kim, H. J.; Shin, J. H.; Bhatia, S. K.; Seo, H. M.; Kim, Y. G.; Lee, Y. K.; Yang, Y. H.; Park, K. Application of diethyl ethoxymethylenemalonate (DEEMM) derivatization for monitoring of lysine decarboxylase activity. J. Mol. Catal. B: Enzym. 2015, 115, 151-154.
- Megias, C.; Giraldo, I. C.; Calle, J. G.; Vioque, J.; Alaiz, M. Determination of l-canavanine and other free amino acids in Vicia disperma (Fabaceae) seeds by precolumn derivatization using diethyl ethoxymethylenemalonate and reversed-phase high-performance liquid chromatography. Talanta 2015, 131, 95-98.