Cookies disclaimer

Estoy de acuerdo utilizamos cookies para mejorar la experiencia de navegación del usuario y para estudiar cómo se utiliza nuestro sitio web. si navega por nuestro sitio web, estará aceptando el uso de las cookies en las condiciones establecidas en la presente política de cookies. esta política puede ser actualizada, por lo que le invitamos a revisarla de forma regular

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

A13776 Diethyl ethoxymethylenemalonate, 98+%

Número CAS
87-13-8
Nombre Alternativo
Ethoxymethylenemalonic acid diethyl ester
Ethoxymethylenepropanedioic acid diethyl ester

Tamaño Precio ($) Cantidad Disponibilidad
50g 19,00
100g 25,80
250g 41,00
500g 74,90
1000g 145,00
Añadir al carrito Añadir al presupuesto al por mayor Ver artículo

Diethyl ethoxymethylenemalonate, 98+%

MDL
MFCD00009148
EINECS
201-725-7

Propiedades químicas

Fórmula
C10H16O5
Peso molecular
216.23
Punto de fusión
-33°
Punto de ebullición
136-139°/10mm
Punto de inflamabilidad
144°(291°F)
Densidad
1.080
Índice de refracción
1.4620
Solubilidad
Miscible with chloroform, dichloromethane and methanol. Immiscible with water.

Aplicaciones

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.

Notas

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

Referencias documentales

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.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (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.

Indicaciones de precaución: 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: Call a POISON CENTER/doctor. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Beilstein
880058
Código de tarifa arancelaria unificado
2918.99
TSCA
Yes
RTECS
OO1100000

Recomendado

Visto recientemente

Productos químicos

Ciencias de la vida

Metales & materiales

Catalizadores

Análisis y material de laboratorio