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Synthetic Routes and Reaction Conditions: One common method for synthesizing 3,4-Difluorobenzonitrile involves the reaction of 3,4-dichlorobenzonitrile with potassium fluoride in the presence of a phase transfer catalyst such as bis-(N,N'-1,3-dimethyl-2-imidazolinyl)-ammonium chloride. The reaction is carried out at a lower temperature with a short reaction time, yielding a high purity product .

Another method involves the reaction of 1,2-difluorobenzene with trichloroacetic chloride in the presence of a Lewis acid catalyst to form 3,4-difluoro-(alpha, alpha, alpha-trichloroacetic) benzene. This intermediate is then reacted with ammonia to obtain 3,4-difluorobenzamide, which is further dehydrated using a halogen-containing dehydration reagent and a catalyst to produce this compound .

Industrial Production Methods: The industrial production of this compound typically follows the synthetic routes mentioned above, with optimizations for large-scale production. The use of recyclable solvents and catalysts, as well as the recrystallization of by-products, helps in reducing production costs and environmental impact .

Chemical Synthesis

Building Block for Fluorinated Compounds
3,4-Difluorobenzonitrile serves as a crucial intermediate in the synthesis of more complex fluorinated organic molecules. It is particularly valuable in creating fluorinated pharmaceuticals and agrochemicals due to its unique reactivity profile. The compound can undergo various chemical transformations, including substitution, reduction, and oxidation reactions.

Reaction Type Product SubstitutionSubstituted benzonitrilesReduction3,4-DifluoroanilineOxidation3,4-Difluorobenzoic acid

Pharmaceutical Applications

Drug Development
In medicinal chemistry, this compound is used as an intermediate for synthesizing potential drug candidates. Its fluorine atoms enhance the pharmacokinetic properties of drugs by improving their metabolic stability and bioavailability. For instance, studies have demonstrated that derivatives of this compound exhibit promising activity against various diseases.

Agricultural Chemistry

Pesticide Synthesis
The compound is also utilized in developing fluorophenoxy herbicides and other agrochemicals. The incorporation of fluorine into herbicides often enhances their efficacy and selectivity. Research has shown that such compounds can effectively control a wide range of weeds while minimizing damage to crops.

Material Science

Liquid Crystal Applications
this compound is explored in the field of liquid crystals due to its unique molecular structure. Its properties make it suitable for use in liquid crystal displays (LCDs) and other electronic applications. The compound's thermal stability and electro-optical characteristics are critical for developing advanced display technologies.

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Case Studies

• Synthesis of Hydroquinone Derivatives A study reported the synthesis of a compound from hydroquinone and this compound. The crystal structure revealed significant intermolecular interactions that could influence the material's properties for applications in pharmaceuticals and materials science .
• Fluorination Reactions Research highlighted the successful fluorination of 3-chloro-4-fluorobenzonitrile to produce this compound with high yields under optimized conditions. This method demonstrates the compound's role as an intermediate in producing more complex fluorinated compounds .
• Agricultural Efficacy Studies Investigations into the efficacy of herbicides synthesized from this compound showed improved weed control compared to traditional herbicides. These findings support the continued exploration of this compound in agricultural applications .

Acetone Applications: Key Considerations for Buyers

3,4-Difluorobenzonitrile (DFBN) is a fluorinated aromatic compound that has garnered attention in various fields, including medicinal chemistry and materials science. Its unique structure, characterized by the presence of two fluorine atoms and a nitrile group, contributes to its distinctive biological activity and potential applications.

Chemical Structure

This compound has the chemical formula C7_77'H4_44'F2_22'N. The presence of fluorine atoms enhances its lipophilicity and alters its electronic properties, which can influence its interaction with biological targets.

Synthesis Methods

The synthesis of this compound can be achieved through halogen-exchange reactions. A notable method involves the reaction of 3,4-dichlorobenzonitrile with potassium fluoride in a solvent such as dimethyl imidazolidinone (DMI) at elevated temperatures. The reaction yields DFBN with significant efficiency when optimized conditions are applied .

Reaction ConditionsYield (%)Notes225 °C, no catalyst11Low yield observed225 °C, with catalyst (Ph4PBr)65Improved yield215 °C11Yield dramatically decreased

Antiviral Properties

Recent studies have explored the antiviral potential of fluorinated compounds similar to DFBN. For instance, fluorinated benzonitriles have been evaluated for their activity against HIV-1. Compounds exhibiting structural similarities to DFBN demonstrated promising anti-HIV activity with low cytotoxicity profiles .

Anticancer Activity

In vitro studies have indicated that fluorinated benzonitriles can exhibit cytotoxic effects on various cancer cell lines. The introduction of fluorine atoms into aromatic compounds often enhances their interaction with biological macromolecules, potentially leading to increased efficacy as anticancer agents .

Structure-Activity Relationship (SAR)

The presence and position of fluorine substituents significantly influence the biological activity of compounds like DFBN. For example, modifications in the substitution pattern can lead to variations in potency against specific targets. This relationship highlights the importance of molecular design in developing new therapeutic agents .

Study on Antiviral Activity

A study focusing on a series of fluorinated compounds demonstrated that certain derivatives exhibited EC50_{50}50' values as low as 6.74 nM against resistant strains of HIV-1. These findings suggest that structural modifications, including those found in DFBN, can lead to enhanced antiviral properties .

Anticancer Efficacy

Research involving the evaluation of DFBN against human sarcoma cell lines revealed significant cytotoxicity comparable to established chemotherapeutics. The mechanism appears to involve interference with key cellular pathways essential for cancer cell survival .

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