(2s,3r)-3-(2,5-Difluorophenyl)-3-hydroxy-2-methyl-4-(1h-1,2,4-triazol-1-yl)butanenitrile

Base Information

• Chemical Name: (2s,3r)-3-(2,5-Difluorophenyl)-3-hydroxy-2-methyl-4-(1h-1,2,4-triazol-1-yl)butanenitrile
• CAS No.: 241479-74-3
• Molecular Formula: C13H12F2N4O
• Molecular Weight: 278.261
• DSSTox Substance ID: DTXSID401129526
• Mol file: 241479-74-3.mol

Synonyms:241479-74-3;(2s,3r)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1h-1,2,4-triazol-1-yl)butanenitrile;Isavuconazole Impurity 6;(2S,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1,2,4-triazol-1-yl)butanenitrile;(alphaS,betaR)-beta-(2,5-Difluorophenyl)-beta-hydroxy-alpha-methyl-1H-1,2,4-triazole-1-butanenitrile;C13H12F2N4O;SCHEMBL1656831;DTXSID401129526;1286729-93-8;CS-Z0013;rel-(2R,3S)-3-(2,5-Difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanenitrile;MFCD28411477;AKOS027250773;DS-9076;AC-31068;CS-0012464;A854829;(2S,3R)-3-(2,5-Difluoro-phenyl)-3-hydroxy-2-methyl-4-[1,2,4]triazol-1-yl-butyronitrile;(S,R)--(2,5-Difluorophenyl)--hydroxy--Methyl-1H-1,2,4-triazole-1-butanenitrile;3-(2,5-Difluoro-phenyl)-3-hydroxy-2-methyl-4-[1,2,4]triazol-1-yl-butyronitrile

Chemical Property of (2s,3r)-3-(2,5-Difluorophenyl)-3-hydroxy-2-methyl-4-(1h-1,2,4-triazol-1-yl)butanenitrile

Chemical Property:

• Boiling Point: 522.5±60.0 °C(Predicted)
• PKA: 10.95±0.29(Predicted)
• PSA: 74.73000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: 1.60378
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 278.09791734
• Heavy Atom Count: 20
• Complexity: 388

Purity/Quality:

99%, ^*data from raw suppliers

(αS,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-methyl-1H-1,2,4-triazole-1-butanenitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C#N)C(CN1C=NC=N1)(C2=C(C=CC(=C2)F)F)O
• Isomeric SMILES: C[C@@H](C#N)[C@](CN1C=NC=N1)(C2=C(C=CC(=C2)F)F)O
• Uses: (αS,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-methyl-1H-1,2,4-triazole-1-butanenitrile is an intermediate in the synthesis of Isavuconazole (I777830), an triazole based antifungal agent for the treatment of invasive fungal infections.

Technology Process of (2s,3r)-3-(2,5-Difluorophenyl)-3-hydroxy-2-methyl-4-(1h-1,2,4-triazol-1-yl)butanenitrile

There total 27 articles about (2s,3r)-3-(2,5-Difluorophenyl)-3-hydroxy-2-methyl-4-(1h-1,2,4-triazol-1-yl)butanenitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.9%

(2S,3S)-2-(2,5-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane + trimethylsilyl cyanide (7677-24-9) → (2S,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butyronitrile (241479-74-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 63 - 68 ℃; for 26h; Solvent; Temperature;

Reference yield: 91.0%

(2R,3S)-2-(2,5-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)-methyl]-oxirane (241479-73-2) + tetra n-butylammoniumfluoride THF + trimethylsilyl cyanide (7677-24-9) → (2S,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butyronitrile (241479-74-3)

Guidance literature:

With magnesium oxide; In tetrahydrofuran; o-xylene;

Reference yield: 84.7%

3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl) butyronitrile → (2S,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butyronitrile (241479-74-3)

Guidance literature:

With [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; In methanol; tert-butyl methyl ether; toluene; at 60 ℃; for 1h; Concentration; Temperature;

upstream raw materials:

(2R,3S)-2-(2,5-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)-methyl]-oxirane

2-hydroxy-2-methylpropanenitrile

trimethylsilyl cyanide

α-chloro-2',5'-difluoroacetophenone

Downstream raw materials:

Isavuconazole

(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramide hydrogensulphate