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)

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

• Language:English Provider:Diethyl ethoxymethylenemalonate
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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.]

Diethyl ethoxymethylenemalonate (87-13-8)Related Product Information

• Diethyl phthalate
• Diethyl fluoromalonate
• acetic acid, triethoxy-, ethyl ester
• Ethyl malonyl chloride
• Diethyl malonate
• Diethyl carbonate
• Diethyl ketomalonate
• Diethyl methylmalonate
• Mefenpyr-diethyl
• 2-AMINODIETHYLMALONATE
• Tris(trimethylsilyl)phosphate
• Diethyl benzylmalonate
• DIETHYL BROMOMALONATE
• ETHOXYLATED COCOAMINE (LATEX STABILIZER)
• Ethoxymethylenemalononitrile
• Ethyl(ethoxymethylene)cyanoacetate
• Isobornyl acrylate
• Sodium erythorbate