(2R,3S)-2-(2,4-Difluorophenyl)-3-methyl-[(1H-1,2,4-triazol-1-yl)methyl]oxirane
[CAS# 127000-90-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Epoxide
• Name: (2R,3S)-2-(2,4-Difluorophenyl)-3-methyl-[(1H-1,2,4-triazol-1-yl)methyl]oxirane
• Synonyms: 1-[[(2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl]methyl]-1,2,4-triazole
• Molecular Formula: C₁₂H₁₁F₂N₃O
• Molecular Weight: 251.23
• CAS Registry Number: 127000-90-2
• EC Number: 806-540-0
• SMILES: C[C@H]1[C@](O1)(CN2C=NC=N2)C3=C(C=C(C=C3)F)F

Properties

• Solubility: Practically insoluble (0.05 g/L) (25 °C), Calc.^*
• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.613, Calc.^*
• Boiling Point: 371.6±52.0 °C (760 mmHg), Calc.^*
• Flash Point: 178.5±30.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

(2R,3S)-2-(2,4-Difluorophenyl)-3-methyl-[(1H-1,2,4-triazol-1-yl)methyl]oxirane is a chemical compound belonging to the class of oxiranes, which are cyclic ethers with a three-membered ring structure. This compound contains several key functional groups, including a difluorophenyl group, a methyl group, and a triazole moiety, making it a valuable structure for various synthetic and medicinal chemistry applications. Its unique combination of properties has drawn interest in the development of novel pharmaceuticals and agrochemicals.

The discovery of (2R,3S)-2-(2,4-Difluorophenyl)-3-methyl-[(1H-1,2,4-triazol-1-yl)methyl]oxirane arose from the ongoing exploration of triazole-containing compounds due to their biological activity and synthetic versatility. Triazole derivatives, particularly those incorporating fluorinated aromatic rings, have been found to exhibit a wide range of biological effects, including antifungal, antibacterial, and anticancer properties. The incorporation of the oxirane structure adds an additional layer of reactivity, making this compound useful in the synthesis of more complex molecules.

One of the primary applications of this compound is in the field of medicinal chemistry, where it is being investigated as a potential lead compound for the development of new drugs. The triazole group, known for its biological activity, can enhance the compound’s interaction with biological targets, making it useful in the design of antifungal or antimicrobial agents. The difluorophenyl group may also contribute to the compound’s lipophilicity, potentially improving its pharmacokinetic properties and allowing it to penetrate biological membranes more effectively.

In addition to its medicinal potential, (2R,3S)-2-(2,4-Difluorophenyl)-3-methyl-[(1H-1,2,4-triazol-1-yl)methyl]oxirane may be used in chemical synthesis as a versatile intermediate for constructing more complex structures. The reactivity of the oxirane ring opens up pathways for further functionalization, allowing the creation of a variety of derivatives with tailored chemical and physical properties. This makes it a valuable building block for the development of agrochemicals, specialty chemicals, and materials.

The ongoing research into (2R,3S)-2-(2,4-Difluorophenyl)-3-methyl-[(1H-1,2,4-triazol-1-yl)methyl]oxirane aims to further explore its reactivity, biological activity, and potential applications. As chemical synthesis and pharmaceutical research continue to evolve, the compound holds promise for a variety of innovative uses in both industry and healthcare.

References

2014. Synthesis of Efinaconazole. Synfacts, 10(7).
DOI: 10.1055/s-0034-1378235

2009. Synthesis of Ravuconazole. Synfacts, 6(2).
DOI: 10.1055/s-0029-1218398