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HomeProduct name listDiethyl ethoxymethylenemalonate

Diethyl ethoxymethylenemalonate

Synonym(s):DEEMM;Diethyl ethoxymethylenemalonate;Ethoxymethylenemalonic acid diethyl ester

  • CAS NO.:87-13-8
  • Empirical Formula: C10H16O5
  • Molecular Weight: 216.23
  • MDL number: MFCD00009148
  • EINECS: 201-725-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-21 22:41:43
Diethyl ethoxymethylenemalonate  Structural

What is Diethyl ethoxymethylenemalonate ?

Chemical properties

CLEAR COLOURLESS TO LIGHT YELLOW LIQUID

The Uses of Diethyl ethoxymethylenemalonate

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.

Safety Profile

Moderately toxic by ingestion. A skin irritant. A combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Likely impurity is diethyl diethoxymethylene malonate which is difficult to separate from diethyl ethoxymethylene malonate by distillation, and it is necessary to follow the course of the distillation by the change in refractive index instead of boiling point. After a low boiling fraction is collected, there is obtained an intermediate fraction (n 20 1.414—1.458), the size of which depends on the amount of the diethoxymethylene compound. This fraction is fractionated through a 5inch Vigreux column (p 11) at low pressure avoiding interruption in heating. Fraction b 108-110o/0.25mm is ca 10o lower than the submitters' fraction (b 97.2o/0.25mm, n D 1.4612—1.4623) [Org Synth Coll Vol III 395 1955, Fuson et al. J Org Chem 11 197 1946, Duff & Kendal J Chem Soc 893 1948]. [Beilstein 3 IV 1192.]

Properties of Diethyl ethoxymethylenemalonate

Melting point: -33°C
Boiling point: 279-283 °C(lit.)
Density  1.080 g/mL at 20 °C(lit.)
vapor pressure  <0.1 hPa
refractive index  n20/D 1.463
Flash point: 311 °F
storage temp.  Store below +30°C.
solubility  Chloroform (Slightly), Ethyl Acetate (Slightly)
form  Liquid
color  Clear colorless to light yellow
Water Solubility  insoluble
BRN  880058
CAS DataBase Reference 87-13-8(CAS DataBase Reference)
NIST Chemistry Reference Propanedioic acid, (ethoxymethylene)-, diethyl ester(87-13-8)
EPA Substance Registry System Propanedioic acid, (ethoxymethylene)-, diethyl ester (87-13-8)

Safety information for Diethyl ethoxymethylenemalonate

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Environment
GHS09
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H317:Sensitisation, Skin
H319:Serious eye damage/eye irritation
H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P273:Avoid release to the environment.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Diethyl ethoxymethylenemalonate

InChIKey LTMHNWPUDSTBKD-UHFFFAOYSA-N

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