CAS 87-13-8: Diethyl 2-(Ethoxymethylene)malonate: A Versatile Chemical Intermedia

Overview

Diethyl 2-(ethoxymethylene)malonate (CAS 87-13-8) is an ester derivative of malonic acid with unique chemical properties. This colorless liquid has a characteristic ester-like aroma and serves as a valuable building block in organic synthesis.The compound’s molecular structure features both ethoxymethylene and ester functional groups. This combination creates multiple reactive sites that enable diverse chemical transformations. It typically boils at 120-122°C under reduced pressure (10 mmHg).

Physical and Chemical Properties

The substance shows excellent solubility in common organic solvents like ethanol and acetone. However, it demonstrates limited solubility in water. Commercial grades typically exceed 98% purity for pharmaceutical applications. Production involves condensing diethyl malonate with ethyl formate. The reaction requires alkali metal alkoxides as catalysts, followed by careful purification processes.

Key Industrial Applications

In pharmaceutical manufacturing, this compound is crucial for producing quinolone antibiotics. It readily reacts with aromatic amines to form quinoline structures found in drugs like norfloxacin. The agrochemical industry uses it to create advanced crop protection agents. Its reactivity helps form pyrimidine structures in modern pesticides.

Material Science Applications

Material scientists value this compound for specialty polymer production. The dual ester groups enable effective cross-linking reactions during polymerization. Recent studies explore its potential in OLED technology. Researchers are investigating its use in creating light-emitting layers for display applications.

Environmental Considerations

While not highly toxic, the compound requires careful handling. It can cause mild eye and skin irritation upon direct contact. In environmental terms, it shows moderate biodegradability. The ester groups hydrolyze under aerobic conditions, facilitating breakdown.

Wastewater Management

Industrial facilities must pretreat wastewater containing this chemical. Its biochemical oxygen demand requires reduction before biological treatment. The ethoxymethylene group degrades faster than saturated analogues. Surface water half-life estimates range between 15-30 days.

Storage Recommendations

Optimal storage uses amber glass or stainless steel containers. Maintaining temperatures below 25°C under inert gas prevents degradation.Users should avoid contact with strong oxidizers and acids. Note that prolonged storage may cause slight yellow discoloration.

Conclusion

This malonate derivative remains essential for pharmaceutical and material applications. Its balanced reactivity supports diverse synthetic pathways. Ongoing research explores greener production methods. Future applications may include advanced materials and biocatalytic processes.