680-65-9 | Diethyl 2,2-difluoromalonate

CAS:680-65-9 | Diethyl 2,2-difluoromalonate ,Description

Diethyl 2,2-difluoromalonate (DDFM) is an organofluorine compound that is widely used in organic synthesis. It is a versatile reagent that is used to synthesize a variety of compounds, including pharmaceuticals, agrochemicals, and biocides. DDFM is also used as a starting material for the synthesis of fluorinated compounds, such as fluorinated polymers and fluorinated surfactants. Additionally, DDFM is used in the synthesis of organofluorine compounds, and can be used as a catalyst for the synthesis of heterocyclic compounds.
 

Synthesis Method Details

Design of the Synthesis Pathway
The synthesis of Diethyl 2,2-difluoromalonate can be achieved through a multi-step reaction pathway starting from readily available starting materials.

Starting Materials
Ethyl chloroacetate, Sodium ethoxide, Bromine, Sodium hydride, Fluorine gas, Methanol, Acetic acid, Sodium bicarbonate

Reaction
Step 1: Ethyl chloroacetate is treated with sodium ethoxide to form diethyl malonate., Step 2: Diethyl malonate is brominated using bromine to form diethyl 2-bromomalonate., Step 3: Diethyl 2-bromomalonate is treated with sodium hydride to form diethyl 2-malonylacetate., Step 4: Diethyl 2-malonylacetate is fluorinated using fluorine gas to form Diethyl 2,2-difluoromalonate., Step 5: The final product is purified by washing with methanol and recrystallization from acetic acid using sodium bicarbonate as a neutralizing agent.

Scientific Research Applications

Diethyl 2,2-difluoromalonate is used in a variety of scientific research applications. It is used in the synthesis of fluorinated compounds, such as fluorinated polymers and fluorinated surfactants. Additionally, Diethyl 2,2-difluoromalonate is used in the synthesis of organofluorine compounds, and can be used as a catalyst for the synthesis of heterocyclic compounds. Furthermore, Diethyl 2,2-difluoromalonate is used in the synthesis of pharmaceuticals, agrochemicals, and biocides.
 

Mechanism of Action

The mechanism of action of Diethyl 2,2-difluoromalonate is based on its ability to act as a nucleophilic reagent. Diethyl 2,2-difluoromalonate is a strong nucleophile, and is capable of forming strong bonds with electrophilic species, such as carbonyl groups. This allows Diethyl 2,2-difluoromalonate to react with a variety of compounds, and is the basis for its use in organic synthesis.
 

Biochemical and Physiological Effects

The biochemical and physiological effects of Diethyl 2,2-difluoromalonate are largely unknown. However, it is known that Diethyl 2,2-difluoromalonate is not toxic and is not known to cause any adverse effects in humans. Additionally, Diethyl 2,2-difluoromalonate is not known to be mutagenic or teratogenic.
 

Advantages and Limitations for Lab Experiments

The advantages of using Diethyl 2,2-difluoromalonate in laboratory experiments include its low cost, availability, and reactivity. Additionally, Diethyl 2,2-difluoromalonate is a versatile reagent, and can be used in a variety of synthetic reactions. The main limitation of Diethyl 2,2-difluoromalonate is that it is not soluble in water, and therefore must be used in organic solvents.
 

Future Directions

For the use of Diethyl 2,2-difluoromalonate include the development of new synthetic methods using Diethyl 2,2-difluoromalonate as a reagent, the synthesis of novel fluorinated compounds, and the development of new catalysts for the synthesis of heterocyclic compounds. Additionally, further research is needed to determine the biochemical and physiological effects of Diethyl 2,2-difluoromalonate, as well as its potential toxicity.

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