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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

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

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 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 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)
An Efficient Cascade Synthesis of Ethyl 3-Amino-5-oxoisoxazolidine-4-carboxylate Derivatives.
Li R, et al.
Synthesis, 49(18), 4341-4349 (2017)
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
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