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Diethyl ethoxymethylenemalonate

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CAS:87-13-8
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CAS:87-13-8
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CAS:87-13-8
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CAS:87-13-8
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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;(Ethoxymethylene)-propanedioic acid diethyl ester
CAS:87-13-8
MF:C10H16O5
MW:216.23
EINECS:201-725-7
Product Categories:Pharmaceuticals;C10 to C11;Carbonyl Compounds;Esters;Pharmaceutical Intermediates;Intermediates & Fine Chemicals
Mol File:87-13-8.mol
Diethyl ethoxymethylenemalonate Structure
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
Fp 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
InChIKeyLTMHNWPUDSTBKD-UHFFFAOYSA-N
LogP1.5-2.1 at pH7
CAS DataBase Reference87-13-8(CAS DataBase Reference)
NIST Chemistry ReferencePropanedioic acid, (ethoxymethylene)-, diethyl ester(87-13-8)
EPA Substance Registry SystemPropanedioic acid, (ethoxymethylene)-, diethyl ester (87-13-8)
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 Temperature215 °C
TSCA Yes
HS Code 29189090
ToxicityLD50 orally in Rabbit: 925 mg/kg LD50 dermal Rat > 2000 mg/kg
MSDS Information
ProviderLanguage
Diethyl ethoxymethylenemalonate English
SigmaAldrich English
ACROS English
ALFA English
Diethyl ethoxymethylenemalonate Usage And Synthesis
Chemical PropertiesCLEAR COLOURLESS TO LIGHT YELLOW LIQUID
UsesDiethyl 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 ProfileModerately toxic by ingestion. A skin irritant. A combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.
Purification MethodsLikely 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.]
Tag:Diethyl ethoxymethylenemalonate(87-13-8) Related Product Information
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