What Is Dimethyl Malonate?
Dimethyl malonate, a colorless to pale yellow liquid, is known chemically as dimethyl propanedioate.
Uses of Dimethyl Malonate
1. Fragrance
Noted for its unique aroma, dimethyl malonate is used both as a fragrance and a food additive. Additionally, it is a precursor for jasmonic acids like methyl dihydrojasmonate, extensively used in high-end fragrances.
2. Barbituric Acid Precursor
Dimethyl malonate reacts with urea under acidic conditions to synthesize barbituric acid, a central component in various CNS depressant drugs, although barbituric acid itself lacks CNS depressant effects.
3. Malonate Ester Synthesis
It plays a crucial role in the malonate ester synthesis method, enabling the creation of α-substituted acetate esters. This involves base-induced carbo anion formation at the α-position of dimethyl malonate, followed by a reaction with an alkyl halide.
4. Knebenagel Condensation
In Knebenagel condensation, dimethyl malonate serves as a substrate for synthesizing alkenes by reacting with ketones or aldehydes, leading to a carbo-anion that attacks the carbonyl carbon, forming an alkene through dehydration condensation.
5. Other Uses
Additionally, it finds application in producing agricultural chemicals and pharmaceuticals.
Properties of Dimethyl Malonate
With the formula C5H8O4 and a molecular weight of 132.11, dimethyl malonate (CAS number 108-59-8) is a liquid at room temperature, featuring a melting point of -62°C and a boiling point of 181°C. Its density is approximately 1.152-1.158 g/ml at 20°C.
It exhibits weak aromatic properties, solubility in alcohols and ethers, and limited water solubility. The compound’s pKa is 13, indicating its mild acidic nature influenced by the presence of two ester groups.
Other Information on Dimethyl Malonate
1. Production Method
Produced from dimethoxymethane and carbon monoxide, or via direct esterification of methanol with malonic acid under azeotropic conditions.
2. Handling and Storage Precautions
Handling Precautions
Avoid exposure to strong oxidizing agents, use protective gear, and operate in a well-ventilated area. Dimethyl malonate is flammable, with a flash point of 83°C, necessitating caution around heat sources to prevent toxic fume release.
Storage Recommendations
It should be stored in glass containers, in cool, well-ventilated areas away from direct sunlight and ignition sources, with the storage location securely locked.