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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.

Storage Class Code

11 - Combustible Solids

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)

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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A process for the synthesis of ?-ketoesters using in-situ generated (trimethylsilyl) malonates
Wang X, et al.
Tetrahedron Letters, 35(50), 9323-9326 (1994)
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)

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