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87-13-8 - Diethyl ethoxymethylenemalonate, 98+% - Ethoxymethylenemalonic acid diethyl ester - Ethoxymethylenepropanedioic acid diethyl ester - A13776 - Alfa Aesar

A13776 Diethyl ethoxymethylenemalonate, 98+%

Codice CAS
87-13-8
Sinonimi
Ethoxymethylenemalonic acid diethyl ester
Ethoxymethylenepropanedioic acid diethyl ester

Dimensioni Prezzo ($) Quantità Disponibilità
50g 19,00
100g 25,80
250g 41,00
500g 74,90
1000g 145,00
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Diethyl ethoxymethylenemalonate, 98+%

MDL
MFCD00009148
EINECS
201-725-7

Proprietà chimiche

Formula
C10H16O5
Peso formula
216.23
Punto di fusione
-33°
Punto di ebollizione
136-139°/10mm
Punto di infiammabilità
144°(291°F)
Densità
1.080
Indice di rifrazione
1.4620
Solubilità
Miscible with chloroform, dichloromethane and methanol. Immiscible with water.

Applicazioni

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.

Note

Incompatible with acids, bases, oxidizing agents and reducing agents.

Letteratura

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 0oC 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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H303-H315-H319-H334-H317

May be harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause allergy or asthma symptoms or breathing difficulties if inhaled. May cause an allergic skin reaction.

Dichiarazioni precauzionali: P284-P261-P280a-P305+P351+P338-P342+P311a-P501a

Wear respiratory protection. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If experiencing respiratory symptoms: Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
880058
Codice tariffe armonizzato
2918.99
TSCA
Yes
RTECS
OO1100000

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