Pyridine-N-oxide

Base Information

• Chemical Name: Pyridine-N-oxide
• CAS No.: 694-59-7
• Deprecated CAS: 110408-34-9
• Molecular Formula: C5H5NO
• Molecular Weight: 95.1008
• Hs Code.: 29333999
• European Community (EC) Number: 211-774-6
• NSC Number: 18250
• UNII: 91F12JJJ4H
• DSSTox Substance ID: DTXSID3061007
• Nikkaji Number: J35.411B
• Wikipedia: Pyridine-N-oxide
• Wikidata: Q287787
• Metabolomics Workbench ID: 54039
• ChEMBL ID: CHEMBL3278446
• Mol file: 694-59-7.mol

Synonyms:pyridine N-oxide;pyridine N-oxide perchlorate

Chemical Property of Pyridine-N-oxide

Chemical Property:

• Appearance/Colour: White to light yellow solid
• Vapor Pressure: 0.0116mmHg at 25°C
• Melting Point: 65-66 °C
• Refractive Index: 1.516
• Boiling Point: 270 °C at 760 mmHg
• PKA: 0.79(at 24℃)
• Flash Point: 117.1 °C
• PSA: 25.46000
• Density: 1.03 g/cm³
• LogP: 1.11510
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Water Solubility.: soluble
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 95.037113783
• Heavy Atom Count: 7
• Complexity: 50

Purity/Quality:

99% ^*data from raw suppliers

Pyridine N-Oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22-40-20/21/22
• Safety Statements: 26-24/25-37/39-36/37/39-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amine Oxides
• Canonical SMILES: C1=CC=[N+](C=C1)[O-]
• General Description: Pyridine-N-oxide serves as an effective oxidant in gold-catalyzed ring-expansion reactions of alkynyl heterocycles, enabling regioselective oxidation and chemoselective migration of endocyclic carbon-heteroatom bonds (C–S, C–N, C–O) to synthesize six- or seven-membered heterocycles with high functional group tolerance and yields.

Technology Process of Pyridine-N-oxide

There total 75 articles about Pyridine-N-oxide 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: 93.0%

2-Picolinic acid (98-98-6) → pyridine N-oxide (694-59-7)

Guidance literature:

With dihydrogen peroxide; In water; at 90 ℃; for 1h;

DOI:10.1080/15533174.2010.522658

Reference yield: 49.0%

pyridine (110-86-1) + Perfluoro-2-hexyl-3-pentyloxaziridine → pyridine N-oxide (694-59-7) + N-(Perfluorohexanoyl)pyridinium-1-aminide

Guidance literature:

In chloroform; trichlorofluoromethane;

DOI:10.1039/p19960002517

Reference yield: 44.0%

pyridine (110-86-1) + perfluoro-cis-2-n-butyl-3-n-propyloxaziridine → pyridine N-oxide (694-59-7) + N-(Perfluorobutanoyl)pyridinium-1-aminide

Guidance literature:

In chloroform; trichlorofluoromethane; at -60 ℃; for 0.5h;

DOI:10.1039/p19960002517

upstream raw materials:

pyridine

monoperoxyphthalic acid

Perbenzoic acid

benzene

Downstream raw materials:

pyridine

[1,2']bipyridinyl-2-one

3-bromo-[1,2']bipyridyl-2-one

2-Pyridone

Refernces

Gold-Catalyzed Ring Expansion of Alkynyl Heterocycles through 1,2-Migration of an Endocyclic Carbon-Heteroatom Bond

10.1002/chem.201504165

The research explores a gold-catalyzed oxidative ring-expansion of alkynyl heterocycles, aiming to develop a mild and efficient method to synthesize valuable six- or seven-membered heterocycles from easily available starting materials. The study employs pyridine-N-oxide as the oxidant and various gold catalysts, such as [PPh3AuNTf2] and [IPrAuNTf2], to facilitate the reaction. The key innovation lies in the regioselective oxidation and chemoselective migration of endocyclic carbon–heteroatom bonds (C–S, C–N, and C–O), with the migratory aptitude order being C–S > C–N > C–O. The reaction demonstrates wide functional group tolerance and high yields, producing polycyclic products in the absence of an oxidant through a ring-expansion/Nazarov cyclization sequence. The findings suggest a new and general protocol for heterocycle synthesis, with potential applications in the construction of complex organic structures.

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