Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

A13776 Diethyl ethoxymethylenemalonate, 98+%

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

Stock No. Size Price ($) Quantity Availability
A13776-18 50g 19.60
A13776-22 100g 26.30
A13776-30 250g 43.50
A13776-36 500g 77.90
A13776-0B 1000g 144.00
Add to Cart Bulk/Specialty Print Quote View Item

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
Storage & Sensitivity
Ambient temperatures.
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: H302-H314-H317-H334-H335

Harmful if swallowed. Causes severe skin burns and eye damage. May cause an allergic skin reaction. May cause allergy or asthma symptoms or breathing difficulties if inhaled. May cause respiratory irritation.

Precautionary Statements: P260-P264b-P270-P271-P272-P280-P285-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P333+P313-P363-P501c

Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. In case of inadequate ventilation wear respiratory protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. If skin irritation or rash occurs: Get medical advice/attention. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
880058
Harmonized Tariff Code
2918.99
TSCA
Yes
RTECS
OO1100000

Recommended

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware