Ethyl potassium malonate
[CAS# 6148-64-7]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic potassium
• Name: Ethyl potassium malonate
• Synonyms: Monoethyl malonate potassium salt; Potassium monoethyl malonate
• Molecular Formula: C₅H₇KO₄
• Molecular Weight: 170.20
• CAS Registry Number: 6148-64-7
• EC Number: 228-156-7
• SMILES: CCOC(=O)CC(=O)[O-].[K+]

Properties

• Melting point: 194 ºC (dec.) (Expl.)
• Water solubility: soluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

Ethyl potassium malonate is an organic potassium salt that plays an important role in synthetic chemistry due to its versatile reactivity and ability to serve as a building block for more complex molecules. The compound is derived from malonic acid, a dicarboxylic acid that is widely used in organic synthesis. The potassium salt form of malonic acid is particularly useful because of its increased solubility and ability to undergo various reactions, making it a valuable reagent in the preparation of other organic compounds.

The discovery of ethyl potassium malonate is tied to the broader development of malonic acid derivatives, which have been studied for centuries due to their significance in both natural and synthetic processes. Malonic acid itself was first synthesized in the 19th century, and its derivatives, including ethyl malonate and ethyl potassium malonate, have been of particular interest to chemists due to their reactivity and versatility in carbon-carbon bond formation. The introduction of potassium as the counterion in the salt enhances the compound's reactivity and makes it particularly useful in a variety of chemical reactions.

One of the most important applications of ethyl potassium malonate is its role in the malonic ester synthesis, a method for constructing carbon-carbon bonds that is widely used in organic chemistry. This process involves the alkylation of ethyl potassium malonate with an alkyl halide, followed by hydrolysis and decarboxylation to form a variety of different carboxylic acids and other organic compounds. This reaction is valuable for the preparation of substituted malonates and related compounds, which can be used as intermediates in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals.

Ethyl potassium malonate is also used in the preparation of β-keto acids, which are important intermediates in the synthesis of a wide range of biologically active compounds. By reacting ethyl potassium malonate with appropriate reagents, chemists can produce a variety of functionalized compounds with potential applications in drug discovery and development. The versatility of ethyl potassium malonate in such reactions is a testament to its value as a chemical building block in the synthesis of complex molecules.

In addition to its role in organic synthesis, ethyl potassium malonate has applications in the preparation of dyes, fragrances, and other specialty chemicals. Its ability to undergo nucleophilic substitution reactions and its high reactivity make it an attractive reagent for a variety of chemical processes. It is also used in the synthesis of heterocyclic compounds, which are important for the development of new drugs and other bioactive molecules.

Despite its usefulness in synthetic chemistry, the application of ethyl potassium malonate requires careful handling due to its reactivity. It is often used in the presence of other reagents, such as bases or acids, to control the course of the reaction and ensure that the desired product is obtained. As with many reactive organic compounds, proper safety precautions are necessary when handling ethyl potassium malonate, particularly when it is being used in large-scale reactions.

In conclusion, ethyl potassium malonate is a valuable chemical compound with broad applications in organic synthesis. Its reactivity and ability to serve as a precursor for a wide range of compounds make it an essential reagent in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals. Its role in the malonic ester synthesis and the preparation of β-keto acids highlights its significance in the development of new bioactive molecules. Ongoing research into the applications of ethyl potassium malonate will likely lead to the discovery of new synthetic methods and the development of novel compounds with therapeutic potential.