3-Bromo-5-nitro-2-(2,2,2-trifluoroethoxy)pyridine

Base Information

• Chemical Name: 3-Bromo-5-nitro-2-(2,2,2-trifluoroethoxy)pyridine
• CAS No.: 1051372-09-8
• Molecular Formula: C₇H₄BrF₃N₂O₃
• Molecular Weight: 301.02
• DSSTox Substance ID: DTXSID00696028
• Wikidata: Q82625442
• Mol file: 1051372-09-8.mol

Synonyms:1051372-09-8;3-bromo-5-nitro-2-(2,2,2-trifluoroethoxy)pyridine;3-BROMO-5-NITRO-2-(2,2,2-TRIFLUORO-ETHOXY)-PYRIDINE;3-Bromo-5-nitro-2-(2,2,2-trifluoroethoxy)-pyridine;SCHEMBL2114422;SCHEMBL17715740;DTXSID00696028;BSB37209;MFCD11858510;SB30396;CS-0341563;A1-03156;3-bromo-5-nitro-2-(2, 2, 2-trifluoro-ethoxy)-pyridine

Chemical Property of 3-Bromo-5-nitro-2-(2,2,2-trifluoroethoxy)pyridine

Chemical Property:

• PSA: 67.94000
• LogP: 3.21660
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 299.93574
• Heavy Atom Count: 16
• Complexity: 258

Purity/Quality:

99% ^*data from raw suppliers

3-Bromo-5-nitro-2-(2,2,2-trifluoro-ethoxy)-pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=NC(=C1Br)OCC(F)(F)F)[N+](=O)[O-]
• Uses: 3-Bromo-5-nitro-2-(2,2,2-trifluoro-ethoxy)-pyridine is used as a reactant in the preparation of N-arylamide oxadiazoles as selective oral CB2 agonists.

Technology Process of 3-Bromo-5-nitro-2-(2,2,2-trifluoroethoxy)pyridine

There total 1 articles about 3-Bromo-5-nitro-2-(2,2,2-trifluoroethoxy)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: 95.0%

3-bromo-2-chloro-5-nitropyridine (5470-17-7) + 2,2,2-trifluoroethanol (75-89-8) → 3-bromo-5-nitro-2-(2,2,2-trifluoro-ethoxy)-pyridine (1051372-09-8)

Guidance literature:

2,2,2-trifluoroethanol; With sodium hydride; In mineral oil; at 0 - 25 ℃; for 0.5h; Inert atmosphere;

3-bromo-2-chloro-5-nitropyridine; In mineral oil; for 16h; Reflux;

Reference yield: 97.0%

3-bromo-5-nitro-2-(2,2,2-trifluoro-ethoxy)-pyridine (1051372-09-8) → 5-bromo-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylamine (1372606-85-3)

Guidance literature:

3-bromo-5-nitro-2-(2,2,2-trifluoro-ethoxy)-pyridine; With hydrogenchloride; tin(ll) chloride; In ethanol; at 25 ℃; for 4h;

With sodium carbonate; In ethyl acetate;

Reference yield:

3-bromo-5-nitro-2-(2,2,2-trifluoro-ethoxy)-pyridine (1051372-09-8) → N-(5-(3,4-dimethylphenyl)-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-nicotinamide (1372605-58-7)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride; tin(ll) chloride / ethanol / 4 h / 25 °C

2: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl )-N,N,N' ,N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 3 h / Inert atmosphere

3: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene; water / 2 h / 90 °C / Inert atmosphere

With hydrogenchloride; O-(benzotriazol-1-yl )-N,N,N' ,N'-tetramethyluronium tetrafluoroborate; sodium carbonate; N-ethyl-N,N-diisopropylamine; tin(ll) chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In ethanol; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

3-bromo-2-chloro-5-nitropyridine

2,2,2-trifluoroethanol

Downstream raw materials:

5-bromo-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylamine

pentanoic acid[5-(4-chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-amide

N-(5-(3,4-dimethylphenyl)-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-nicotinamide

N-(5-(4-chloro-3-methylphenyl)-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-nicotinamide

Refernces

• 1、 -. "N-(5-CYCLOALKYL- OR 5-HETEROCYCLYL-)-PYRIDIN-3-YL CARBOXAMIDES". Paragraph 0120; 0121. . Retrieved 2013/03/28.
• 2、 -. "N-PYRIDIN-3-YL OR N-PYRAZIN-2-YL CARBOXAMIDES". Page/Page column 41. . Retrieved 2012/05/04.