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Merck
모든 사진(1)

문서

D97754

Sigma-Aldrich

Diethyl malonate

ReagentPlus®, 99%

동의어(들):

Malonic acid diethyl ester

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About This Item

Linear Formula:
CH2(COOC2H5)2
CAS Number:
Molecular Weight:
160.17
Beilstein:
774687
EC Number:
MDL number:
UNSPSC 코드:
12352100
PubChem Substance ID:
NACRES:
NA.22

vapor density

5.52 (vs air)

vapor pressure

1 mmHg ( 40 °C)

제품 라인

ReagentPlus®

분석

99%

형태

liquid

refractive index

n20/D 1.413 (lit.)

bp

199 °C (lit.)

mp

−51-−50 °C (lit.)

density

1.055 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)CC(=O)OCC

InChI

1S/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3

InChI key

IYXGSMUGOJNHAZ-UHFFFAOYSA-N

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일반 설명

Diethyl malonate is diethyl ester of malonic acid. It is widely used as a versatile building block for introducing the malonate functional group into molecules. Acylation of diethyl malonate using magnesium chloride and triethylamine is reported. K2CO3-catalyzed 1,4-addition reaction of diethyl malonate with various substituted 1,2-allenic ketones yields polyfunctionalized β,γ-unsaturated enones.

애플리케이션

Diethyl malonate was used to investigate Knoevenagel condensation reactions in microreactor using zeolite catalysts obtained by grafting amino groups onto NaX and CsNaX zeolites. It may be used in the synthesis of diethyl benzylidenemalonate by base catalyzed Knoevenagel condensation with benzaldehyde. It may be used in the synthesis of α-aryl malonates.

포장

Packaged in glass bottles

법적 정보

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

픽토그램

Exclamation mark

신호어

Warning

유해 및 위험 성명서

Hazard Classifications

Eye Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point (°F)

199.4 °F - closed cup

Flash Point (°C)

93 °C - closed cup

개인 보호 장비

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)


시험 성적서(COA)

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문서 라이브러리 방문

Shengming Ma et al.
The Journal of organic chemistry, 68(23), 8996-9002 (2003-11-08)
The K2CO3 (10 mol %)-catalyzed 1,4-addition reaction of diethyl malonate with various substituted 1,2-allenic ketones leading to polyfunctionalized beta,gamma-unsaturated enones 3 or 4 was studied. With 3-unsubstituted 1-substituted-1,2-allenyl ketones, the highly selective formation of beta,gamma-unsaturated enones 4 was observed; with
Solvent-free organocatalytic Michael addition of diethyl malonate to nitroalkenes: the practical synthesis of Pregabalin and ?-nitrobutyric acid derivatives
J Liu, et al.
Tetrahedron, 67, 636-640 (2011)
Edward J Hennessy et al.
Organic letters, 4(2), 269-272 (2002-02-14)
[reaction: see text] A general method for the synthesis of alpha-aryl malonates is described. The coupling of an aryl iodide and diethyl malonate in the presence of Cs(2)CO(3) and catalytic amounts of copper(I) iodide and 2-phenylphenol affords the alpha-aryl malonate
Integration of heterogeneous catalysts into complex synthetic routes: sequential vs. one-pot reactions in a (Knoevenagel+ Mukaiyama-Michael+ hydrogenation+ transesterification) sequence.
Fraile JM, et al.
Catalysis Science & Technology, 3(2), 436-443 (2013)
Lian Jin Liu et al.
Nucleosides, nucleotides & nucleic acids, 30(10), 784-797 (2011-10-05)
Novel 5'-norcarbocyclic adenosine phosphonic acid analogues with 6'-electropositive moiety such as spirocyclopropane were designed and synthesized from the commercially available diethylmalonate 5. Regioselective Mitsunobu reaction proceeded in the presence of an allylic functional group at a low reaction temperature in

문서

Knoevenagel Condensation is an organic reaction named after Emil Knoevenagel. It is a classic C-C bond formation reaction and a modification of the Aldol Condensation.

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