Dimethyl 1,3-acetonedicarboxylate
[CAS# 1830-54-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Methyl ester compound
• Name: Dimethyl 1,3-acetonedicarboxylate
• Synonyms: Dimethyl 3-oxoglutarate; Dimethyl 3-oxopentanedioate
• Molecular Formula: C₇H₁₀O₅
• Molecular Weight: 174.15
• CAS Registry Number: 1830-54-2
• EC Number: 217-385-8
• SMILES: COC(=O)CC(=O)CC(=O)OC

Properties

• Density: 1.185
• Meltng point: 16-17 °C
• Boiling point: 150 °C (25 mmHg)
• Refractive index: 1.443-1.445
• Water solubility: approx. 120 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317
• Safety Statements: P261-P272-P280-P302+P352-P321-P333+P313-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Dimethyl 1,3-acetonedicarboxylate, with the chemical formula C7H10O4, is a versatile compound widely used in organic synthesis due to its unique chemical properties. This substance is recognized for its role as a building block in the synthesis of various organic molecules, owing to its reactivity and functional groups.

The discovery of dimethyl 1,3-acetonedicarboxylate emerged from the broader study of dicarboxylate esters and their applications in organic chemistry. The compound is synthesized through the esterification of 1,3-acetonedicarboxylic acid with methanol. The reaction yields dimethyl 1,3-acetonedicarboxylate, which features two ester groups attached to a central acetone unit. This structure imparts significant reactivity to the compound, making it useful in various chemical transformations.

One of the primary applications of dimethyl 1,3-acetonedicarboxylate is in the synthesis of complex organic molecules. The compound serves as a key intermediate in the preparation of pharmaceuticals, agrochemicals, and other specialty chemicals. Its ability to undergo nucleophilic substitution reactions allows for the introduction of diverse functional groups, facilitating the creation of a wide range of compounds with tailored properties.

In medicinal chemistry, dimethyl 1,3-acetonedicarboxylate is used to synthesize bioactive compounds with potential therapeutic applications. The compound's structure enables the incorporation of various functional groups, which can be further modified to develop drugs with specific activities. For example, it can be used as a precursor in the synthesis of inhibitors or modulators of biological targets, contributing to drug discovery and development efforts.

Additionally, dimethyl 1,3-acetonedicarboxylate finds applications in materials science, where it is employed to create polymers and advanced materials. The compound's reactivity allows it to be incorporated into polymer matrices, enhancing the properties of the resulting materials. These polymers can exhibit improved mechanical strength, thermal stability, or other desirable characteristics, making them suitable for various industrial applications.

The compound is also valuable in research settings, where it is used to explore new chemical reactions and synthesis methods. Its ability to participate in diverse chemical transformations provides researchers with opportunities to develop novel methodologies and gain insights into reaction mechanisms.

Overall, dimethyl 1,3-acetonedicarboxylate is an important compound in organic chemistry with broad applications in synthesis, medicinal chemistry, and materials science. Its unique chemical properties and reactivity make it a valuable tool for creating complex molecules and advanced materials, contributing to advancements in various scientific and industrial fields.

References

2024. Synthesis and PASS-assisted evaluation of new heterocyclic compounds containing hydroquinoline scaffolds. BMC Chemistry.
DOI: 10.1186/s13065-024-01267-3

2021. Reactions on Saturated and Unsaturated Carbons. Steric and Stereoelectronic Effects in Organic Chemistry.
DOI: 10.1007/978-3-030-75622-2_2

2020. Synthesis and chemical properties of 3-alkoxycarbonylchromones and 3-alkoxalylchromones. Chemistry of Heterocyclic Compounds.
DOI: 10.1007/s10593-020-02784-4