5-Methylpyridin-2-YL trifluoromethanesulfonate

Base Information

• Chemical Name: 5-Methylpyridin-2-YL trifluoromethanesulfonate
• CAS No.: 154447-03-7
• Molecular Formula: C7H6 F3 N O3 S
• Molecular Weight: 241.191
• DSSTox Substance ID: DTXSID00571886
• Nikkaji Number: J1.083.098B
• Wikidata: Q82460072
• Mol file: 154447-03-7.mol

Synonyms:154447-03-7;(5-methylpyridin-2-yl) trifluoromethanesulfonate;5-METHYLPYRIDIN-2-YL TRIFLUOROMETHANESULFONATE;5-METHYL-2-(TRIFLUOROMETHANESULFONYL)OXYPYRIDINE;Methanesulfonic acid,1,1,1-trifluoro-, 5-methyl-2-pyridinyl ester;SCHEMBL16548489;DTXSID00571886;IULKVMJKTKNACP-UHFFFAOYSA-N;2-Trifluoromethanesulfonyloxy-5-methylpyridine;J-400318

Chemical Property of 5-Methylpyridin-2-YL trifluoromethanesulfonate

Chemical Property:

• Boiling Point: 283.0±40.0 °C(Predicted)
• PKA: -1.69±0.29(Predicted)
• PSA: 64.64000
• Density: 1.504±0.06 g/cm3(Predicted)
• LogP: 2.69920
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 241.00204871
• Heavy Atom Count: 15
• Complexity: 308

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN=C(C=C1)OS(=O)(=O)C(F)(F)F

Technology Process of 5-Methylpyridin-2-YL trifluoromethanesulfonate

There total 2 articles about 5-Methylpyridin-2-YL trifluoromethanesulfonate 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: 92.0%

5-methyl-pyridin-2-ol (1003-68-5,91914-06-6) + trifluoromethylsulfonic anhydride (358-23-6) → 5-methyl-2-(trifluoromethanesulfonyl)oxypyridine (154447-03-7)

Guidance literature:

With pyridine; at -12 - 0 ℃; for 0.5h; Schlenk technique; Inert atmosphere;

DOI:10.15227/orgsyn.078.0051

Reference yield:

(5-methyl-pyridin-2-yl)amine (1603-41-4) → 5-methyl-2-(trifluoromethanesulfonyl)oxypyridine (154447-03-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid; sodium nitrite / water / 1 h / 0 - 95 °C

2: pyridine / 0.5 h / -12 - 0 °C / Schlenk technique; Inert atmosphere

With pyridine; sulfuric acid; sodium nitrite; In water;

DOI:10.15227/orgsyn.078.0051

Reference yield: 66.0%

triphenylbismuthane (603-33-8) + 5-methyl-2-(trifluoromethanesulfonyl)oxypyridine (154447-03-7) → 5-methyl-2-phenylpyridine (27012-22-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In N,N-dimethyl-formamide; at 130 ℃; Inert atmosphere; Sealed tube;

DOI:10.1002/ejoc.201300850

upstream raw materials:

5-methyl-pyridin-2-ol

trifluoromethylsulfonic anhydride

(5-methyl-pyridin-2-yl)amine

Downstream raw materials:

5-methyl-2-phenylpyridine