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Sigma-Aldrich

Ethyl potassium malonate

98%

Synonym(s):

Monoethyl malonate potassium salt, Potassium monoethyl malonate

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About This Item

Linear Formula:
C2H5OCOCH2CO2K
CAS Number:
6148-64-7
Molecular Weight:
170.20
Beilstein:
3721682
EC Number:
228-156-7
MDL number:
MFCD00035603
UNSPSC Code:
12352100
PubChem Substance ID:
24862007
NACRES:
NA.22

Quality Level

200

Assay

98%

form

solid

mp

194 °C (dec.) (lit.)

SMILES string

[K+].CCOC(=O)CC([O-])=O

InChI

1S/C5H8O4.K/c1-2-9-5(8)3-4(6)7;/h2-3H2,1H3,(H,6,7);/q;+1/p-1

InChI key

WVUCPRGADMCTBN-UHFFFAOYSA-M

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General description

Ethyl potassium malonate (potassium ethyl malonate) reacts with aryl nitriles in the presence of zinc chloride and a catalytic amount of Hünig′s base to yield β-amino acrylates. Ethyl potassium malonate is formed as an intermediate during the synthesis of ethyl tert-butyl malonate.

Application

Ethyl potassium malonate (potassium ethyl malonate) may be used to generate (trimethylsilyl)ethyl malonate in situ, which can be acylated to prepare a variety of β-ketoesters or alkylidene malonates.

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Jae Hoon Lee et al.
The Journal of organic chemistry, 72(26), 10261-10263 (2007-12-01)
Reaction of aryl nitriles with potassium ethyl malonate in the presence of zinc chloride and a catalytic amount of Hünig's base provided beta-amino acrylates in moderate to good yield. Compared to the classical Blaise reaction, this reaction is safer (endothermic)
Ethyl tert-Butyl Malonate.
Strube RE.
Organometallic Syntheses, 34-34 (1963)
A process for the synthesis of ?-ketoesters using in-situ generated (trimethylsilyl) malonates
Wang X, et al.
Tetrahedron Letters, 35(50), 9323-9326 (1994)

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