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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:
Molecular Weight:
216.23
Beilstein:
880058
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

Signal Word

Warning

Hazard Statements

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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 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)
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)
Synthesis of fused pyrimidinone and quinolone derivatives in an automated high-temperature and high-pressure flow reactor.
Tsoung J, et al.
The Journal of Organic Chemistry, 82(2), 1073-1084 (2017)
Benoit Bach et al.
Analytica chimica acta, 732, 114-119 (2012-06-13)
This paper reports on the development of an optimized method for the simultaneous analysis of eight biogenic amines (histamine, methylamine, ethylamine, tyramine, putrescine, cadaverine, phenethylamine, and isoamylamine). The analytical method thus proposed has the following advantages: the easy derivatization of

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