1-(2,2-Difluorobenzo[D][1,3]dioxol-5-YL)cyclopropanecarbonitrile
[CAS# 862574-87-6]

Identification

• Classification: Organic raw materials >> Nitrile compound
• Name: 1-(2,2-Difluorobenzo[D][1,3]dioxol-5-YL)cyclopropanecarbonitrile
• Molecular Formula: C₁₁H₇F₂NO₂
• Molecular Weight: 223.18
• CAS Registry Number: 862574-87-6
• SMILES: C1CC1(C#N)C2=CC3=C(C=C2)OC(O3)(F)F

Discovory and Applicatios

1-(2,2-Difluorobenzo[D][1,3]dioxol-5-YL)cyclopropanecarbonitrile is a chemical compound that has garnered attention in the field of medicinal chemistry and agrochemical research due to its unique structural features and potential biological activities. The discovery of this compound is closely linked to the exploration of cyclopropane derivatives, which are known for their stability and versatility in synthetic chemistry.

The synthesis of 1-(2,2-Difluorobenzo[D][1,3]dioxol-5-YL)cyclopropanecarbonitrile involves the introduction of a cyclopropane ring to a difluorinated benzodioxole system. The difluorobenzo[d][1,3]dioxole moiety is particularly noteworthy because the presence of fluorine atoms enhances the compound's lipophilicity and metabolic stability. These properties are critical for the development of compounds with favorable pharmacokinetic profiles. The cyclopropane ring adds rigidity to the molecular structure, which can be advantageous in optimizing the interaction of the compound with biological targets.

One of the primary applications of this compound is in the development of new agrochemicals, specifically as a pesticide or herbicide. The structural features of 1-(2,2-Difluorobenzo[D][1,3]dioxol-5-YL)cyclopropanecarbonitrile make it a potential candidate for controlling pests and weeds that have developed resistance to existing treatments. Its fluorinated components contribute to the increased potency and selectivity of the compound, which is crucial in minimizing environmental impact while maximizing efficacy.

In medicinal chemistry, the compound has shown promise as a lead molecule in the development of drugs targeting neurological disorders. The benzodioxole core is a common scaffold in molecules that interact with the central nervous system, and the addition of a cyclopropane group can enhance the binding affinity of the compound to neurotransmitter receptors. Early studies suggest that 1-(2,2-Difluorobenzo[D][1,3]dioxol-5-YL)cyclopropanecarbonitrile could be developed into a therapeutic agent for conditions such as anxiety, depression, or even epilepsy, where modulation of specific neural pathways is required.

The discovery of this compound highlights the importance of incorporating fluorine atoms into organic molecules to improve their biological and chemical properties. Fluorination often leads to increased metabolic stability, resistance to biodegradation, and enhanced binding interactions, making such compounds valuable in both pharmaceutical and agricultural applications.

Synthetically, 1-(2,2-Difluorobenzo[D][1,3]dioxol-5-YL)cyclopropanecarbonitrile is typically prepared through a cyclopropanation reaction, where a precursor containing the benzodioxole moiety is treated with a suitable cyclopropanating agent. This reaction is usually carried out under controlled conditions to ensure the retention of the delicate fluorinated groups. The resulting product is a compound with significant potential for further functionalization, allowing chemists to explore a wide range of derivatives for different applications.

As research progresses, the versatility and utility of 1-(2,2-Difluorobenzo[D][1,3]dioxol-5-YL)cyclopropanecarbonitrile will likely be expanded, particularly in the fields of agrochemical and pharmaceutical development. Its unique structure serves as a foundation for designing new molecules that address current challenges in both areas, offering solutions that are more effective and environmentally sustainable.