Diethyl ethoxymethylenemalonate (DEEM), identified by its CAS No. 87-13-8, is a highly versatile and indispensable organic compound in the chemical industry. With a molecular formula of C10H16O5 and a molecular weight of 216.23 g/mol, DEEM typically appears as a colorless to light yellow transparent liquid. Its unique chemical structure, featuring multiple active groups, allows it to participate in a wide array of reactions, making it a pivotal intermediate for numerous synthetic pathways.

Key physical and chemical properties underscore DEEM's utility. It possesses a boiling point typically ranging from 279°C to 283°C and a melting point of -33°C. Its density is approximately 1.08 g/mL at 20°C, and it exhibits a refractive index between 1.4610 and 1.4630. While largely insoluble in water, DEEM is readily soluble in common organic solvents, simplifying its handling and integration into various formulations. The purity of commercial-grade DEEM is typically 99.0% or higher, ensuring reliability for demanding applications.

The applications of Diethyl ethoxymethylenemalonate span across several critical sectors. In the pharmaceutical industry, DEEM serves as a crucial intermediate in the synthesis of a variety of life-saving drugs. It is indispensable for the production of fluoroquinolone antibiotics such as lomefloxacin, norfloxacin, and romefloxacin, as well as the antimalarial drug chloroquine. Furthermore, its role extends to the synthesis of the anti-cancer drug imatinib mesylate and essential nutrients like vitamin B6 and folic acid. Its unique chemical properties allow for the introduction of specific functional groups necessary for desired pharmacological activity.

Beyond pharmaceuticals, DEEM is widely utilized in the synthesis of pesticides and agrochemicals. It is a key building block for herbicides such as bensulfuron-methyl and tribenuron-methyl, contributing to effective crop protection by enabling the formulation of potent insecticides and pesticides. Its integration with other active ingredients often enhances their efficiency, allowing for reduced chemical usage while maintaining robust pest control.

More broadly, Diethyl ethoxymethylenemalonate is an invaluable reagent in general organic synthesis. It acts as a versatile building block and nucleophile, participating in condensation polymerization and cyclization reactions with various substances. This makes it instrumental in the synthesis of diverse compounds, including peptides, peptide derivatives, polymers, small molecules, and biodegradable polymers, contributing significantly to scientific research and innovation across various chemical fields.

The synthesis of Diethyl ethoxymethylenemalonate commonly involves the condensation reaction of diethyl malonate with triethyl orthoformate, followed by the removal of ethanol. This established method ensures a high yield of the product. Proper storage is crucial for maintaining its quality; it should be stored in a cool, sealed place, away from direct sunlight, to prevent degradation.

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