124627-86-7

Basic information

• Product Name: 1-[(2R,3S)-2-(2,4-DIFLUORO-PHENYL)-3-METHYL-OXIRANYLMETHYL]-1H-[1,2,4]TRIAZOLE
• Synonyms: 1-[(2R,3S)-2-(2,4-DIFLUORO-PHENYL)-3-METHYL-OXIRANYLMETHYL]-1H-[1,2,4]TRIAZOLE
• CAS NO: 124627-86-7
• Molecular Formula: C₁₂H₁₁F₂N₃O
• Molecular Weight: 251.2320464
• Mol File: 124627-86-7.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 371.6±52.0 °C(Predicted)
• Appearance: /
• Density: 1.41±0.1 g/cm3(Predicted)
• Storage Temp.: Amber Vial, Refrigerator
• Solubility: Chloroform (Sparingly), Methanol (Sparingly)
• PKA: 2.75±0.10(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: 1-[(2R,3S)-2-(2,4-DIFLUORO-PHENYL)-3-METHYL-OXIRANYLMETHYL]-1H-[1,2,4]TRIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(2R,3S)-2-(2,4-DIFLUORO-PHENYL)-3-METHYL-OXIRANYLMETHYL]-1H-[1,2,4]TRIAZOLE(124627-86-7)
• EPA Substance Registry System: 1-[(2R,3S)-2-(2,4-DIFLUORO-PHENYL)-3-METHYL-OXIRANYLMETHYL]-1H-[1,2,4]TRIAZOLE(124627-86-7)

Safety Data

• Hazardous Substances Data: 124627-86-7(Hazardous Substances Data)

Usage

Description

1-[(2R,3S)-2-(2,4-DIFLUORO-PHENYL)-3-METHYL-OXIRANYLMETHYL]-1H-[1,2,4]TRIAZOLE is a complex organic compound characterized by its unique molecular structure, which features a triazole ring fused with an oxiranylmethyl group. 1-[(2R,3S)-2-(2,4-DIFLUORO-PHENYL)-3-METHYL-OXIRANYLMETHYL]-1H-[1,2,4]TRIAZOLE is known for its potential applications in the pharmaceutical industry, particularly in the development of antifungal agents.

Uses

Used in Pharmaceutical Industry:
1-[(2R,3S)-2-(2,4-DIFLUORO-PHENYL)-3-METHYL-OXIRANYLMETHYL]-1H-[1,2,4]TRIAZOLE is used as a key intermediate in the synthesis of sulfur-containing antifungal azoles. Its unique structure contributes to the development of effective antifungal agents that target various fungal pathogens, providing a valuable tool in the fight against fungal infections.
The compound's role in the synthesis of antifungal azoles is significant, as these azoles are known for their broad-spectrum antifungal activity. They are commonly used to treat a wide range of fungal infections, including those caused by Candida, Aspergillus, and other pathogenic fungi. By serving as an intermediate in the synthesis of these azoles, 1-[(2R,3S)-2-(2,4-DIFLUORO-PHENYL)-3-METHYL-OXIRANYLMETHYL]-1H-[1,2,4]TRIAZOLE plays a crucial role in the development of new and improved antifungal medications.

Upstream product

• 132507-89-2 (2R,3S)-2-(2,4-Difluoro-phenyl)-1-[1,2,4]triazol-1-yl-butane-2,3-diol 
• 124-63-0 methanesulfonyl chloride 
• 126918-20-5 (2R^*,3R^*)-2-(2,4-Difluorophenyl)-1,2,3-butanetriol 
• 132563-81-6 1-(2,4-difluorophenyl)-2-(tetrahydropyranyloxy)propan-1-one 
• 126918-19-2 (2S,3S)-2-(2,4-Difluoro-phenyl)-3-(tetrahydro-pyran-2-yloxy)-butane-1,2-diol 
• 126918-18-1 (2S^*,3R^*)-2-(2,4-Difluorophenyl)-1-(dimethylisopropoxysilyl)-3-(tetrahydropyran-2-yloxy)-2-butanol 
• 126918-21-6 (2R^*,3R^*)-2-(2,4-Difluorophenyl)-1,3-bis(methanesulfonyloxy)-2-butanol 
• 132507-77-8 Trifluoro-acetic acid (1R,2S)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl ester 
• 124627-86-7 (2R^*,3S^*)-2-(2,4-Difluorophenyl)-3-methyl-2-<(1H-1,2,4-triazol-1-yl)methyl>oxirane 
• 132507-89-2 threo-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol 
• 126945-34-4 Methanesulfonic acid (1S,2S)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl ester 
• 41253-21-8 sodium triazole 
• 1829-92-1 triethylsulfonium iodide 
• 86404-63-9 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone 

Downstream Products

• 126917-48-4 (2R,3R)-3-Azido-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol 
• 135272-34-3 (2R,3R)-2-(2,4-difluorophenyl)-3-mercapto-1-[1H-1,2,4-triazol-1-yl]-2-butanol 
• 132507-77-8 Trifluoro-acetic acid (1R,2S)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl ester 
• 150803-24-0 (2R,3R)-2-(2,4-difluorophenyl)-3-(2H-tetrazol-2-yl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol 

Relevant articles and documents

Asymmetric Catalytic Epoxidation of Terminal Enones for the Synthesis of Triazole Antifungal Agents

An enantioselective epoxidation of α-substituted vinyl ketones was realized to construct the key epoxide intermediates for the synthesis of various triazole antifungal agents. The reaction proceeded efficiently in high yields with good enantioselectivities by employing a chiral N,N′-dioxide/ScIII complex as the chiral catalyst and 35% aq. H2O2 as the oxidant. It enabled the facile transformation for optically active isavuconazole, efinaconazole, and other potential antifungal agents.

Design, synthesis, and structure-activity relationship studies of novel triazole agents with strong antifungal activity against Aspergillus fumigatus

The incidence of invasive fungal infections has dramatically increased for several decades. In order to discover novel antifungal agents with broad spectrum and anti-Aspergillus efficacy, a series of novel triazole derivatives containing 1,2,3-benzotriazin-4-one was designed and synthesized. Most of the compounds exhibited stronger in vitro antifungal activities against tested fungi than fluconazole. Moreover, 6m showed comparable antifungal activity against seven pathogenic strains as voriconazole and albaconazole, especially against Aspergillus fumigatus (MIC = 0.25 μg/ml), and displayed moderate antifungal activity against fluconazole-resistant strains of Candida albicans. A clear SAR study indicated that compounds with groups at the 7-position resulted in novel antifungal triazoles with more effectiveness and a broader-spectrum.

PROCESS FOR PRODUCING EPOXY ALCOHOL COMPOUND

A compound represented by formula (II): (where Ar represents a phenyl group optionally substituted by 1 to 3 substituents selected from the group consisting of a halogen atom and a trifluoromethyl group, and R represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms) is produced by step A: reacting trimethyl oxosulfonium salt or trimethyl sulfonium salt with a base in a solvent, and removing the resulting solid to obtain a trimethyl oxosulfonium ylide solution or a trimethyl sulfonium ylide solution; and step B: reacting a compound represented by formula (I): and the solution obtained in step A, and the compound represented by formula (II) can be derived to a compound represented by formula (V): that is useful for production of an antifungal agent.