Production Method 1

53229-58-6

31420-47-0

826-34-6

Reaction Conditions

1.1 Reagents: Thionyl chloride ;  4 h, rt
2.1 0.5 h, heated

Reference

Studies and potential synthesis of muscarinic agents

Garst, John E., 1974, , ,

Production Method 2

5617-74-3

31420-47-0

826-34-6

Reaction Conditions

1.1 0.5 h, heated

Reference

Studies and potential synthesis of muscarinic agents

Garst, John E., 1974, , ,

Production Method 3

878-14-8

31420-47-0

826-34-6

Reaction Conditions

1.1 Reagents: Water
1.2 Reagents: Thionyl chloride
2.1 0.5 h, heated

Reference

Studies and potential synthesis of muscarinic agents

Garst, John E., 1974, , ,

cis-2-methoxycarbonylcyclopropanecarboxylic acid Raw materials

• cis-2-benzyloxycarbonylcyclopropanecarboxylic acid
• 3-Oxabicyclo[3.1.0]hexane-2,4-dione
• 1,2-Cyclopropanedicarboxylic acid, ethyl methyl ester

cis-2-methoxycarbonylcyclopropanecarboxylic acid Preparation Products

• cis-2-methoxycarbonylcyclopropanecarboxylic acid (31420-47-0)
• dimethyl cis-cyclopropane-1,2-dicarboxylate (826-34-6)

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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Cyclopropanecarboxylic acids
• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Cyclopropanecarboxylic acids and derivatives Cyclopropanecarboxylic acids

cis-2-methoxycarbonylcyclopropanecarboxylic acid (CAS No. 31420-47-0)

cis-2-methoxycarbonylcyclopropanecarboxylic acid (CAS No. 31420-47-0) is a unique and versatile organic compound that has garnered significant attention in the fields of organic chemistry, pharmaceutical research, and materials science. This compound, characterized by its distinctive cyclopropane ring and carboxylic acid functionality, exhibits a range of properties that make it an important intermediate in the synthesis of various bioactive molecules and pharmaceuticals.

The chemical structure of cis-2-methoxycarbonylcyclopropanecarboxylic acid consists of a cyclopropane ring with a carboxylic acid group and a methoxycarbonyl group attached to adjacent carbon atoms. The cis configuration of these functional groups imparts specific stereochemical properties that are crucial for its reactivity and biological activity. The cyclopropane ring, being highly strained, is prone to undergo various chemical transformations, making it a valuable building block in synthetic chemistry.

Recent studies have highlighted the potential applications of cis-2-methoxycarbonylcyclopropanecarboxylic acid in the development of novel pharmaceuticals. For instance, researchers at the University of California, San Francisco, have reported that derivatives of this compound exhibit potent anti-inflammatory and anti-cancer properties. The cyclopropane ring and the carboxylic acid functionality contribute to the compound's ability to interact with specific biological targets, such as enzymes and receptors involved in inflammatory pathways and cancer cell proliferation.

In the realm of materials science, cis-2-methoxycarbonylcyclopropanecarboxylic acid has been explored for its potential use in the synthesis of advanced polymers and coatings. The strained cyclopropane ring can be readily opened through various chemical reactions, leading to the formation of polymers with unique mechanical and thermal properties. These polymers have shown promise in applications ranging from biomedical devices to high-performance coatings.

The synthesis of cis-2-methoxycarbonylcyclopropanecarboxylic acid typically involves multi-step processes that require precise control over reaction conditions to ensure the desired stereochemistry. Common synthetic routes include the cyclization of appropriate precursors followed by functional group transformations. Recent advancements in catalytic methods have improved the efficiency and selectivity of these syntheses, making it more accessible for large-scale production.

From a safety perspective, while cis-2-methoxycarbonylcyclopropanecarboxylic acid is not classified as a hazardous material, it is important to handle it with care due to its reactivity. Proper storage conditions, such as keeping it away from moisture and heat sources, are recommended to maintain its stability and purity.

In conclusion, cis-2-methoxycarbonylcyclopropanecarboxylic acid (CAS No. 31420-47-0) is a multifaceted compound with significant potential in both pharmaceutical research and materials science. Its unique chemical structure and reactivity make it an invaluable tool for chemists and researchers working on the development of new drugs and advanced materials. As research continues to uncover new applications and properties, this compound is likely to play an increasingly important role in various scientific disciplines.

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