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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+%

CAS Number
87-13-8
Synonyms
Ethoxymethylenemalonic acid diethyl ester
Ethoxymethylenepropanedioic acid diethyl ester

Size Price ($) Quantity Availability
50g 17.46
100g 25.19
250g 36.18
500g 75.60
1000g 141.68
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Diethyl ethoxymethylenemalonate, 98+%

MDL
MFCD00009148
EINECS
201-725-7

Chemical Properties

Formula
C10H16O5
Formula Weight
216.23
Melting point
-33°
Boiling Point
136-139°/10mm
Flash Point
144°(291°F)
Density
1.080
Refractive Index
1.4620
Solubility
Miscible with chloroform, dichloromethane and methanol. Immiscible with water.

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.

Notes

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

Literature 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 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.

GHS Hazard and Precautionary Statements

Hazard Statements: H334-H315-H319-H317-H303

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

Precautionary Statements: P285-P261-P280-P305+P351+P338-P342+P311-P362-P312-P363-P304+P341-P501a

In case of inadequate ventilation wear respiratory protection. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/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 or doctor/physician. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Wash contaminated clothing before reuse. IF INHALED: If breathing is difficult, remove to fresh air and keep at rest in a position comfortable for breathing. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
880058
Harmonized Tariff Code
2918.99
TSCA
Yes
RTECS
OO1100000

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