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Diethyl ethoxymethylenemalonate

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Diethyl ethoxymethylenemalonate Basic information

Product Name:
Diethyl ethoxymethylenemalonate
Synonyms:
  • 1,1-DICARBETHOXY-2-ETHOXYETHYLENE
  • 2,2-DICARBETHOXYVINYL ETHYL ETHER
  • AKOS BBS-00004230
  • LABOTEST-BB LT02094814
  • ETHYL A-CARBETHOXY-B-ETHOXYACRYLATE
  • ETHYL ETHOXYMETHYLENE MALONATE
  • ETHYL 3-ETHOXY-2-(ETHOXYCARBONYL)ACRYLATE
  • EMME
CAS:
87-13-8
MF:
C10H16O5
MW:
216.23
EINECS:
201-725-7
Product Categories:
  • Pharmaceuticals
  • C10 to C11
  • Pharmaceutical Intermediates
  • Carbonyl Compounds
  • Esters
  • Intermediates & Fine Chemicals
Mol File:
87-13-8.mol
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Diethyl ethoxymethylenemalonate Chemical Properties

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
InChIKey
LTMHNWPUDSTBKD-UHFFFAOYSA-N
LogP
1.5-2.1 at pH7
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)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22-36/37/38-42/43
Safety Statements 
26-36/37/39-27-24/25
WGK Germany 
1
RTECS 
OO1100000
Autoignition Temperature
215 °C
TSCA 
Yes
HS Code 
29189090
Toxicity
LD50 orally in Rabbit: 925 mg/kg LD50 dermal Rat > 2000 mg/kg

MSDS

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Diethyl ethoxymethylenemalonate Usage And Synthesis

Chemical Properties

CLEAR COLOURLESS TO LIGHT YELLOW LIQUID

Uses

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.]

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