6-Nitro-2,2'-bipyridine

Base Information

• Chemical Name: 6-Nitro-2,2'-bipyridine
• CAS No.: 944709-04-0
• Molecular Formula: C₁₀H₇N₃O₂
• Molecular Weight: 201.184
• DSSTox Substance ID: DTXSID40695752
• Nikkaji Number: J3.107.061I
• Wikidata: Q82625032
• Mol file: 944709-04-0.mol

Synonyms:6-NITRO-2,2'-BIPYRIDINE;944709-04-0;2-nitro-6-(2-pyridyl)pyridine;DTXSID40695752;J-400804

Chemical Property of 6-Nitro-2,2'-bipyridine

Chemical Property:

• Boiling Point: 388.7oC at 760 mmHg
• Flash Point: 188.9oC
• PSA: 71.60000
• Density: 1.314g/cm3
• LogP: 2.57500
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 201.053826475
• Heavy Atom Count: 15
• Complexity: 229

Purity/Quality:

99% ^*data from raw suppliers

6-NITRO-2,2'-BIPYRIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=NC(=C1)C2=NC(=CC=C2)[N+](=O)[O-]

Technology Process of 6-Nitro-2,2'-bipyridine

There total 4 articles about 6-Nitro-2,2'-bipyridine 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: 71.0%

2-bromo-6-nitro-pyridine (21203-78-1) + 2-trimethylstannylpyridine (13737-05-8) → 6-nitro-2,2'-bipyridine (944709-04-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; for 16h; Inert atmosphere; Reflux;

DOI:10.1246/bcsj.80.902

Reference yield: 60.0%

2-bromo-6-nitro-pyridine (21203-78-1) + 2-tri-n-butylstannylpyridine (17997-47-6) → 6-nitro-2,2'-bipyridine (944709-04-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride; In N,N-dimethyl-formamide; at 110 ℃; Inert atmosphere;

DOI:10.1039/c2dt31308a

Reference yield:

2-Amino-6-bromopyridine (19798-81-3,1184170-10-2) → 6-nitro-2,2'-bipyridine (944709-04-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid; dihydrogen peroxide / 5 - 20 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride / N,N-dimethyl-formamide / 110 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; dihydrogen peroxide; lithium chloride; In N,N-dimethyl-formamide;

DOI:10.1039/c2dt31308a

upstream raw materials:

2-bromo-6-nitro-pyridine

2-trimethylstannylpyridine

2-tri-n-butylstannylpyridine

2-Amino-6-bromopyridine

Refernces

Unusual nitro-coordination of europium(iii) and terbium(iii) with pyridinyl ligands

10.1039/c2dt31308a

The study investigates a new family of ligands based on picoline, bipyridine, and terpyridine, each containing a nitro moiety, and their coordination and sensitization abilities for lanthanide ions, specifically europium(III) (Eu(III)) and terbium(III) (Tb(III)). The researchers synthesized four ligands: 6-nitro-2,2'-bipyridine (5a), 6'-methyl-6-nitro-2,2'-bipyridine (5b), 6-nitro-2,2';6',2''-terpyridine (5c), and bis(pyridin-2-ylmethyl)(6-nitro-pyridin-2-ylmethyl)amine (6). These ligands were found to coordinate not only through the pyridine nitrogen but also through an oxygen atom of the nitro moiety. The study characterized three new complexes using X-ray single crystal diffraction: 5cTb (a terpyridine-nitro derivative with Tb(NO3)3), its Eu(III) analog 5cEu, and 6Eu (a tripodal amine with a nitro-derivatized pyridine with Eu(CF3SO3)3). All four ligands demonstrated the ability to sensitize Eu(III) and Tb(III) luminescence. The study also explored the photophysical properties of these ligands and their complexes, finding that while the ligands adequately positioned their singlet and triplet states for energy transfer, the process was inefficient, likely due to competing energy transfer pathways involving the nitro group.

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