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
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 | n |
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) |
Exclamation Mark Irritant GHS07 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 |
Abamectin manufacturer
JSK Chemicals
SRIKAR Labs
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