170862-36-9

Basic information

• Product Name: [R-(R*,S*)]-β-(2,4-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanenitrile
• Synonyms: (αS,βR)-β-(2,4-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanenitrile;[R-(R*,S*)]-β-(2,4-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanenitrile;(2S,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-Methyl-4-(1H-1,2,4-triazol-1-yl)butanenitrile;(alphaS,betaR)-beta-(2,4-Difluorophenyl)-beta-hydroxy-alpha-methyl-1H-1,2,4-triazole-1-butanenitrile
• CAS NO: 170862-36-9
• Molecular Formula: C₁₃H₁₂F₂N₄O
• Molecular Weight: 278.2573864
• Mol File: 170862-36-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 178-182 °C(Solv: isopropanol (67-63-0))
• Boiling Point: 522.5±60.0 °C(Predicted)
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 11.15±0.29(Predicted)
• CAS DataBase Reference: [R-(R*,S*)]-β-(2,4-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: [R-(R*,S*)]-β-(2,4-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanenitrile(170862-36-9)
• EPA Substance Registry System: [R-(R*,S*)]-β-(2,4-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanenitrile(170862-36-9)

Safety Data

• Hazardous Substances Data: 170862-36-9(Hazardous Substances Data)

Usage

Chemical Properties

Beige Solid

Uses

(αS,βR)-β-(2,4-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanenitrile is used in the preparation of triazole antifungal agents.

Upstream product

• 86404-63-9 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone 
• 166948-49-8 (2R,3R)-3-[3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-3-(1H-1,2,4-triazol-1-yl)]butanoic acid 
• 861718-85-6 3-chloro-2-(2,4-difluorophenyl)-2-(trimethylsilanyloxy)propionaldehyde 
• 861718-83-4 (S)-3-chloro-2-(2,4-difluorophenyl)-2-((trimethylsilyl)oxy)propanenitrile 
• 51336-94-8 2-chloro-1-(2,4-dichlorophenyl)ethanone 
• 132507-89-2 (2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol 
• 7677-24-9 trimethylsilyl cyanide 
• 124627-86-7 1-(((2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)-methyl)-1H-1,2,4-triazole 
• 1188327-50-5 diethylaluminium cyanide 
• 211926-45-3 (2RS,3S)-2-(2,4-difluoro)phenyl-3-methyl-4-triphenylmethyloxy-1,2-epoxybutane 
• 170862-48-3 (S)-2-(2,4-difluorophenyl)-3-methyl-4-(triphenylmethyloxy)-1,2-butene 
• 5804-85-3 diethylaluminium cyanide 
• 135270-13-2 1-(((2R,3R)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)-methyl)-1H-1,2,4-triazole 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 

Downstream Products

• 170863-34-0 (2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanethioamide 
• 1175536-51-2 (2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanethioamide hydrosulfate 
• 219872-85-2 (2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanamide 
• 182760-06-1 ravuconazole 
• 207224-81-5 (2R,3R)-2-(2,4-Difluoro-phenyl)-3-{4-[4-(2H-tetrazol-5-yl)-phenyl]-thiazol-2-yl}-1-[1,2,4]triazol-1-yl-butan-2-ol 
• 207224-83-7 (2R,3R)-2-(2,4-Difluoro-phenyl)-1-[1,2,4]triazol-1-yl-3-{4-[4-(1H-[1,2,4]triazol-3-yl)-phenyl]-thiazol-2-yl}-butan-2-ol 
• 368421-60-7 4-{2-[(1R,2R)-2-(2,4-Difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl]-thiazol-4-yl}-thiobenzamide 
• 170863-35-1 (2R,3R)-2-(2,4-Difluoro-phenyl)-3-[4-(4-methylsulfanyl-phenyl)-thiazol-2-yl]-1-[1,2,4]triazol-1-yl-butan-2-ol 

Relevant articles and documents

AN IMPROVED PROCESS FOR THE PREPARATION OF TRIAZOLE DERIVATIVES

The present invention relates to an improved process for the preparation of triazole derivatives such as ravuconazole and isavuconazole.

An enantioselective synthesis of the key intermediate for triazole antifungal agents; Application to the catalytic asymmetric synthesis of efinaconazole (jublia)

A new synthetic route, the shortest reported to date, to access a key intermediate for the synthesis of various triazole antifungal agents was developed. The elusive tetrasubstituted stereogenic center that is essential in advanced triazole antifungal agents was constructed via the catalytic asymmetric cyanosilylation of a ketone. The subsequent transformations were performed in two one-pot operations, enhancing the overall synthetic efficiency toward the intermediate. This streamlined synthetic approach was successfully applied to efficient enantioselective syntheses of efinaconazole (Jublia) and ravuconazole.

Improved chiral synthesis of ravuconazole

A short, elegant, and high yielding synthesis of ravoconazole is presented. The key step of this synthesis is an enantioselective palladium-catalyzed chiral zinc-allene addition reaction. The starting materials are 2-chloro-1-(2,4-difluorophenyl)-ethanone and (R)-4-phenylbutyn-2-ol obtained from enzymatic resolution of its racemate. Copyright Taylor & Francis Group, LLC.