2-Hydroxy-6-(4-trifluoromethylphenyl)pyridine

Base Information

• Chemical Name: 2-Hydroxy-6-(4-trifluoromethylphenyl)pyridine
• CAS No.: 1111110-54-3
• Molecular Formula: C12H8F3NO
• Molecular Weight: 239.197
• Mol file: 1111110-54-3.mol

Synonyms:2-Hydroxy-6-(4-trifluoromethylphenyl)pyridine;6-(4-(TrifluoroMethyl)phenyl)pyridin-2-ol

Chemical Property of 2-Hydroxy-6-(4-trifluoromethylphenyl)pyridine

Chemical Property:

• PSA: 33.12000
• LogP: 3.47300
• Storage Temp.: 2-8°C

Purity/Quality:

95% ^*data from raw suppliers

6-(4-(Trifluoromethyl)phenyl)pyridin-2-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Hydroxy-6-(4-trifluoromethylphenyl)pyridine

There total 3 articles about 2-Hydroxy-6-(4-trifluoromethylphenyl)pyridine 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: 67.0%

4-bromo-trans-crotonic acid ethyl ester (37746-78-4) + 4-CF3C6H4CN (455-18-5) → 6-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one (1111110-54-3)

Guidance literature:

4-bromo-trans-crotonic acid ethyl ester; 4-CF₃C₆H₄CN; With chloro-trimethyl-silane; zinc; In 1,4-dioxane; for 4h; Reflux;

With potassium carbonate; In 1,4-dioxane; water; at 20 ℃; for 0.5h;

DOI:10.1055/s-0037-1610171

Reference yield: 38.0%

6-methoxy-2-{4-(trifluoromethyl)phenyl}pyridine (1202026-99-0) → 6-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one (1111110-54-3)

Guidance literature:

With 2,4,6-trimethyl-pyridine; lithium iodide; for 6h; Reflux;

DOI:10.1055/s-0034-1378331

Reference yield:

p-trifluoromethylphenyl bromide (402-43-7) + 2-methoxy-6-(tri-n-butylstannyl)pyridine (164014-94-2) → 6-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one (1111110-54-3)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride; copper(l) chloride / tetrahydrofuran / 18 h / 70 °C

2: 2,4,6-trimethyl-pyridine; lithium iodide / 6 h / Reflux

With 2,4,6-trimethyl-pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) chloride; lithium chloride; lithium iodide; In tetrahydrofuran; 1: |Stille Cross Coupling;

DOI:10.1055/s-0034-1378331

upstream raw materials:

p-trifluoromethylphenyl bromide

2-methoxy-6-(tri-n-butylstannyl)pyridine

6-methoxy-2-{4-(trifluoromethyl)phenyl}pyridine

4-bromo-trans-crotonic acid ethyl ester

Downstream raw materials:

2-phenoxy-6-(4-(trifluoromethyl)phenyl)pyridine

Refernces

• 1、 Smith, Charlotte L.,Hirschh?user, Christoph,Malcolm, Georgia K.,Nasrallah, Daniel J.,Gallagher, Timothy. "Synthesis of mono- and diaza-'pyridones' via stille coupling of alkoxystannanes". . p. 1904 - 1908. Retrieved 2014/08/18.