2,6-Dichloropyridine N-oxide

Base Information

• Chemical Name: 2,6-Dichloropyridine N-oxide
• CAS No.: 2587-00-0
• Molecular Formula: C5H3Cl2NO
• Molecular Weight: 163.991
• Hs Code.: 29333999
• European Community (EC) Number: 679-082-0
• NSC Number: 136569
• DSSTox Substance ID: DTXSID50355830
• Nikkaji Number: J31.409I
• Wikidata: Q82134897
• Mol file: 2587-00-0.mol

Synonyms:2,6-dichloropyridine N-oxide

Chemical Property of 2,6-Dichloropyridine N-oxide

Chemical Property:

• Appearance/Colour: Slightly yellow-cream crystalline powder
• Melting Point: 138-142oC(lit.)
• Boiling Point: 344.2 °C at 760 mmHg
• PKA: -2.26±0.10(Predicted)
• Flash Point: 162 °C
• PSA: 25.46000
• Density: 1.47 g/cm³
• LogP: 2.42190
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 162.9591691
• Heavy Atom Count: 9
• Complexity: 91

Purity/Quality:

98% ^*data from raw suppliers

2,6-Dichloropyridine-1-oxide ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=[N+](C(=C1)Cl)[O-])Cl
• General Description: 2,6-Dichloropyridine N-oxide (Cl2pyNO) is a versatile oxidant used in catalytic systems, particularly in conjunction with ruthenium porphyrin complexes, to facilitate selective alkene oxidation. It enables controlled transformations of alkenes into diverse products such as epoxides, aldehydes, and 1,2-diols by modulating oxidant loading, offering a mild and efficient alternative to traditional methods involving toxic or costly reagents like OsO4. 2,6-DICHLOROPYRIDINE N-OXIDE plays a key role in advancing "one-pot" cascade reactions for functional molecule synthesis.

Technology Process of 2,6-Dichloropyridine N-oxide

There total 3 articles about 2,6-Dichloropyridine 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: 90.15%

2,6-dichloropyridine (2402-78-0) → 2,6-dichloropyridine N-oxide (2587-00-0)

Guidance literature:

With dihydrogen peroxide; trifluoroacetic acid; at 80 ℃; for 2h; Reagent/catalyst; Temperature;

Reference yield:

2,6-dichloropyridine (2402-78-0) + dihydrogen peroxide (7722-84-1) → 2,6-dichloropyridine N-oxide (2587-00-0)

Guidance literature:

With trifluoroacetic acid;

Reference yield:

→ 2,6-dichloropyridine N-oxide (2587-00-0)

Guidance literature:

DOI:10.1039/J29670001235 DOI:10.1039/c29710000028

upstream raw materials:

2,6-dichloropyridine

dihydrogen peroxide

Downstream raw materials:

2,6-dichloropyridine

2,4,6-trichloropyridine

4-nitro-2,6-dichloro-pyridine

2-chloropyridine

Refernces

A mild catalytic oxidation system: Ruthenium porphyrin and 2,6-dichloropyridine n-oxide applied for alkene dihydroxylation

10.1002/adsc.201000455

The research aimed to develop a mild and efficient catalytic oxidation system for the transformation of alkenes into various functional molecules, such as epoxides, aldehydes, and 1,2-diols. The study utilized a ruthenium porphyrin complex, dichlororuthenium(IV) meso-tetrakis(2,6-dichlorophenyl)porphyrin [Ru(IV)(TDCPP)Cl2], as a catalyst and 2,6-dichloropyridine N-oxide (Cl2pyNO) as the oxidant. The innovative aspect of this research was the ability to control the reaction pathway and product distribution by adjusting the oxidant loading, which allowed for the selective formation of aldehydes, epoxides, or 1,2-diols in moderate to excellent yields. This approach represents an advancement in the field of alkene dihydroxylation, as it provides a single catalytic system capable of producing three different types of compounds through "one-pot" cascade reactions, overcoming the limitations of previous methods that relied on more toxic and expensive catalysts like OsO4.