Ethyl potassium malonate Chemical Properties

Melting point:

194 °C (dec.) (lit.)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Methanol (Slightly), Water (Slightly)

form 

Powder or Cyrstals

color 

White

PH

pH(50g/l, 25℃) : 5.5～8.0

Water Solubility 

soluble

Sensitive 

Hygroscopic

BRN 

3721682

InChI

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

InChIKey

WVUCPRGADMCTBN-UHFFFAOYSA-M

SMILES

C(C(=O)O)C(=O)OCC.[KH]

CAS DataBase Reference

6148-64-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

2

HS Code 

29171910

MSDS

• Language:English Provider:Ethyl potassium malonate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Ethyl potassium malonate Usage And Synthesis

Chemical Properties

white crystals or powder

Uses

Ethyl potassium malonate is used as a competitive inhibitor of the enzyme succinate dehydrogenase. It acts as a precursor to produce (trimethylsilyl)ethyl malonate, which is utilized to prepare beta-ketoesters by acylation. Further, it reacts with aryl nitriles to prepare beta-amino acrylates in the presence of zinc chloride and a catalytic amount of Hünig's base. In addition to this, it serves as an intermediate for the preparation of ethyl tert-butyl malonate.

Uses

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.

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.

Synthesis

Step 1: Add diethyl malonate (100g, 0.625mol) and anhydrous ethanol (400ml) to a 2 liter round bottom flask fitted with a magnetic stirrer. A solution of potassium hydroxide (35 g, 0.624 mol) in anhydrous ethanol (400 ml) was slowly added dropwise at room temperature. After the dropwise addition, the reaction mixture was continued to be stirred overnight. Subsequently, the reaction mixture was heated to reflux and then slowly cooled to room temperature. The first products were isolated by vacuum filtration through a large No. 2 sintered glass funnel and dried at room temperature for 1 hour. The filtrate was concentrated to about 500 ml and then cooled to room temperature to precipitate the second batch of crystals. Combining the two batches of product, the total yield was 97.7 g with 92% yield.

References

[1] Patent: WO2012/25861, 2012, A1. Location in patent: Page/Page column 20
[2] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 18, p. 4995 - 5010
[3] Angewandte Chemie - International Edition, 2011, vol. 50, # 19, p. 4470 - 4474
[4] Chemistry - A European Journal, 2003, vol. 9, # 17, p. 4222 - 4231
[5] Tetrahedron, 2012, vol. 68, # 9, p. 2113 - 2120

Ethyl potassium malonate(6148-64-7)Related Product Information

• Potassium iodide
• Ethyl malonyl chloride
• Diethyl malonate
• Malonic acid
• Diethyl methylmalonate
• Potassium Acetate
• Potassium Citrate
• 3-tert-Butoxy-3-oxopropanoic acid
• Potassium 3-methoxy-3-oxopropanoate
• Ethyl hydrogen malonate
• Dimethyl malonate
• MONO-ETHYL SUCCINATE
• Ethyl Succinyl Chloride
• Diethyl ethylmalonate
• Potassium persulfate
• Potassium chloride
• Diisopropyl malonate
• TERT-BUTYL ETHYL MALONATE