3-(Bicyclo[2.2.1]hept-5-en-2-yl)-1,1,1-trifluoro-2-(trifluoromethyl)propan-2-ol
[CAS# 196314-61-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: 3-(Bicyclo[2.2.1]hept-5-en-2-yl)-1,1,1-trifluoro-2-(trifluoromethyl)propan-2-ol
• Synonyms: 5-(2-Hydroxy-2,2-bistrifluoromethyl)ethyl-2-norbornene
• Molecular Formula: C₁₁H₁₂F₆O
• Molecular Weight: 274.20
• CAS Registry Number: 196314-61-1
• SMILES: C1C2CC(C1C=C2)CC(C(F)(F)F)(C(F)(F)F)O

Properties

• Density: 1.374
• Boiling point: 262 °C
• Flash point: 112 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovery and Applications

3-(Bicyclo[2.2.1]hept-5-en-2-yl)-1,1,1-trifluoro-2-(trifluoromethyl)propan-2-ol is a unique compound that combines a bicyclo[2.2.1]heptane ring structure with a trifluoromethyl group, resulting in a molecule with interesting physical and chemical properties. The compound was first synthesized in the 1990s as part of a broader effort to create fluorinated organic molecules that could potentially be used in a variety of high-tech industries. The researchers aimed to exploit the unique reactivity and stability provided by the fluorinated group combined with the rigid and versatile bicyclo[2.2.1]heptane structure. Its bicyclo[2.2.1]heptane ring provides a rigid and non-planar structure that affects the physical properties of the molecule; the trifluoromethyl group contributes to increased electronegativity and lipophilicity, enhancing the molecule's stability and biological activity.

The compound's unique structure allows it to be incorporated into advanced polymer systems, improving thermal stability, chemical resistance, and mechanical properties. These polymers can be used in high-performance applications such as coatings, electronics, and aerospace materials. The molecule can be used as a surface modifier for materials that require specific surface properties such as hydrophobicity and oleophobicity. This is particularly useful for creating non-stick and anti-fouling surfaces for industrial and consumer products.

The fluorinated groups in the compound improve its metabolic stability and bioavailability, making it a valuable scaffold in drug design. It can be used to enhance the pharmacokinetic properties of drug candidates, improving their efficacy and reducing side effects. The rigid structure and lipophilicity of the compound allow it to act as a prodrug, delivering active drugs in a more controlled manner. This can optimize the release of the drug in the body, enhancing the therapeutic effect.

In agrochemical research, the compound is a starting point for the synthesis of new pesticides. Its stability and unique reactivity are suitable for the development of agents that can effectively target pests while being resistant to environmental degradation. It can also be used to develop herbicides that need to be stable and effective under a variety of environmental conditions, providing broad weed control.

The structure of the compound allows it to be used as a ligand or catalyst in homogeneous catalysis. Its stereo and electronic properties can be fine-tuned to improve the selectivity and efficiency of catalytic processes, especially in asymmetric syntheses. It is also valuable in the development of polymerization catalysts, especially those involving fluorinated monomers. These catalysts can produce polymers with unique properties that are difficult to achieve with conventional catalysts.

The compound can serve as a valuable intermediate in organic synthesis. Its functional groups allow for a range of chemical transformations, making it useful for building more complex molecules in pharmaceutical and materials research. Its stable and unique structure makes it a versatile building block for the synthesis of a wide range of compounds, including those used in medicinal chemistry and specialty chemicals.

References

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