(R)-1-(4-Chloro-2-(3-Methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanol

Base Information

• Chemical Name: (R)-1-(4-Chloro-2-(3-Methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanol
• CAS No.: 1033805-26-3
• Molecular Formula: C₁₂H₁₀ClF₃N₂O
• Molecular Weight: 290.672
• Mol file: 1033805-26-3.mol

Synonyms:(R)-1-(4-chloro-2-(3-methyl-1H-pyrazole-1-yl)phenyl)-2,2,2-trifluoroethane-1-ol

Chemical Property of (R)-1-(4-Chloro-2-(3-Methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanol

Chemical Property:

• Boiling Point: 393.1±42.0 °C(Predicted)
• PKA: 11.44±0.14(Predicted)
• Density: 1.42±0.1 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

(R)-1-(4-Chloro-2-(3-Methyl-1h-Pyrazol-1-Yl)Phenyl)-2,2,2-Trifluoroethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• General Description: (R)-1-(4-Chloro-2-(3-Methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanol is a key chiral intermediate in the synthesis of telotristat ethyl, a drug used to treat carcinoid syndrome. It can be efficiently synthesized via biocatalytic reduction of its corresponding prochiral acetophenone using engineered variants of Lactobacillus fermentum short-chain dehydrogenase/reductase 1 (LfSDR1), achieving high enantiomeric excess (>99% ee) and conversion (>99%). This enzymatic process enables scalable production with high isolated yield (75.6%) under optimized conditions.

Technology Process of (R)-1-(4-Chloro-2-(3-Methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanol

There total 6 articles about (R)-1-(4-Chloro-2-(3-Methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanol 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: 94.0%

1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanone (1125828-30-9) → (R)-1-(4-chloro-2-(3-methyl-1H-pyrazole-1-yl)phenyl)-2,2,2-trifluoroethane-1-ol (1033805-26-3)

Guidance literature:

With potassium formate; dichloro(pentamethylcyclopentadienyl)iridium (III) dimer; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine; In water; acetonitrile; at 40 ℃; for 2h;

Reference yield: 91.2%

2,2,2-Trifluoroacetaldehyde (75-90-1) + 1-(2-bromo-5-chlorophenyl)-3-methyl-1H-pyrazole (1125828-26-3) → (R)-1-(4-chloro-2-(3-methyl-1H-pyrazole-1-yl)phenyl)-2,2,2-trifluoroethane-1-ol (1033805-26-3)

Guidance literature:

1-(2-bromo-5-chlorophenyl)-3-methyl-1H-pyrazole; With isopropylmagnesium bromide; In toluene; at 0 ℃; Inert atmosphere;

2,2,2-Trifluoroacetaldehyde; With copper(I) bromide dimethylsulfide complex; C₃₇H₃₀NO₂P; In toluene; at -20 ℃; for 3h; Inert atmosphere;

Reference yield: 86.0%

3-Methylpyrazole (1453-58-3) + (R)-1-(2-bromo-4-chlorophenyl)-2,2,2-trifluoroethane-1-ol (1033805-25-2) → (R)-1-(4-chloro-2-(3-methyl-1H-pyrazole-1-yl)phenyl)-2,2,2-trifluoroethane-1-ol (1033805-26-3)

Guidance literature:

With potassium carbonate; copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; In toluene; at 130 ℃; for 12h;

upstream raw materials:

3-Methylpyrazole

(R)-1-(2-bromo-4-chlorophenyl)-2,2,2-trifluoroethane-1-ol

1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanone

2,2,2-Trifluoroacetaldehyde

Downstream raw materials:

(S)-3-(4-(2-amino-6-((R)-1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)phenyl)-2-(tert-butoxycarbonylamino)propanoic acid

(S)-2-amino-3-(4-(2-amino-6-((R)-1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)-phenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)phenyl)propanoic acid

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