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D94208

Sigma-Aldrich

Diethyl ethoxymethylenemalonate

99%

Synonym(s):

DEEMM, Ethoxymethylenemalonic acid diethyl ester

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About This Item

Linear Formula:
C2H5OCH=C(COOC2H5)2
CAS Number:
87-13-8
Molecular Weight:
216.23
Beilstein:
880058
EC Number:
201-725-7
MDL number:
MFCD00009148
UNSPSC Code:
12352100
PubChem Substance ID:
24894294
NACRES:
NA.22

Quality Level

100

Assay

99%

form

liquid

refractive index

n20/D 1.462 (lit.)

bp

279-281 °C (lit.)

density

1.07 g/mL at 25 °C (lit.)

SMILES string

CCO\C=C(\C(=O)OCC)C(=O)OCC

InChI

1S/C10H16O5/c1-4-13-7-8(9(11)14-5-2)10(12)15-6-3/h7H,4-6H2,1-3H3

InChI key

LTMHNWPUDSTBKD-UHFFFAOYSA-N

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Application

Diethyl ethoxymethylenemalonate can be used as a precursor to synthesize pyrimidinones, thiazolopyrimidines, thiazolopyrimidinones, triazolo [1, 5-a] pyrimidines, pyrimido[2,1-b]benzothiazoles and ethyl 3-amino-5-oxoisoxazolidine-4-carboxylate derivatives.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H315,H317,H319,H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1A

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

291.2 °F - closed cup

Flash Point(C)

144 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000366295
0000366295
0000302047
STBK4590
0000112521

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Synthesis and structure activity relationship investigation of triazolo [1, 5-a] pyrimidines as CB2 cannabinoid receptor inverse agonists.
Tabrizi M A, et al.
European Journal of Medicinal Chemistry, 113, 11-27 (2016)
Microwave Assisted Synthesis of Fused Thiazoles in Multicomponent System and Their in vitro Antitumor, Antioxidant, and Antimicrobial Activities.
El?Borai M A, et al.
Journal of Heterocyclic Chemistry, 54(2), 1031-1041 (2017)
Synthesis and in vitro antitumor activity of new series of benzothiazole and pyrimido [2, 1-b] benzothiazole derivatives.
Gabr M T, et al.
European Journal of Medicinal Chemistry, 85, 576-592 (2014)
J Girón et al.
Analytical biochemistry, 206(1), 155-160 (1992-10-01)
A recently reported methodology for amino acid analysis by HPLC has been adapted for quantification of N-epsilon-(2-propenal)lysine (a modified lysine by reaction with malondialdehyde that has been found in enzymatic digests of foods and in urine) in biological samples. We
T Nishihata et al.
Journal of pharmacobio-dynamics, 7(9), 607-613 (1984-09-01)
Diethylethoxymethylene malonate (DEEMM) and diethyl maleate (DEM) enhanced the rectal absorption of cefmetazole in rats when studies were carried out using in vivo, in situ rectal loop and in vitro rectal everted sac method. Since an increase of cefmetazole transport
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