6-Bromo-2,2'-bipyridine N-oxide

Base Information

• Chemical Name: 6-Bromo-2,2'-bipyridine N-oxide
• CAS No.: 205052-95-5
• Molecular Formula: C₁₀H₇BrN₂O
• Molecular Weight: 251.082
• DSSTox Substance ID: DTXSID50445124
• Nikkaji Number: J1.544.016C
• Wikidata: Q82263458
• Mol file: 205052-95-5.mol

Synonyms:6-BROMO-2,2'-BIPYRIDINE N-OXIDE;205052-95-5;DTXSID50445124;6-Bromo-2,2'-bipyridine 1-oxide;J-400772;2-Bromo-1-oxo-6-(pyridin-2-yl)-1lambda~5~-pyridine

Chemical Property of 6-Bromo-2,2'-bipyridine N-oxide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 89.5 °C
• Boiling Point: 453.653°C at 760 mmHg
• PKA: 2.22±0.34(Predicted)
• Flash Point: 228.161°C
• PSA: 38.35000
• Density: 1.551g/cm³
• LogP: 2.93960
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 249.97418
• Heavy Atom Count: 14
• Complexity: 191

Purity/Quality:

2-BROMO-6-(PYRIDIN-2-YL)PYRIDIN-1-IUM-1-OLATE 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=[N+](C(=CC=C2)Br)[O-]

Technology Process of 6-Bromo-2,2'-bipyridine N-oxide

There total 3 articles about 6-Bromo-2,2'-bipyridine 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: 70.0%

2,2'-bipyridyl N-oxide (33421-43-1) → 6-bromo-2,2'-bipyridine N-oxide (205052-95-5) + 5,6-dibromo-2,2'-bipyridine N-oxide + 4,5,6-tribromo-2,2'-bipyridine N-oxide

Guidance literature:

2,2'-bipyridyl N-oxide; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -70 ℃; for 0.5h;

With bromocyane; In tetrahydrofuran; hexane; at -70 ℃; for 0.25h;

DOI:10.1021/jo972022i

Reference yield: 66.0%

2,6-dibromopyridin N-oxide (25373-69-7) + 2-tri-n-butylstannylpyridine (17997-47-6) → 6-bromo-2,2'-bipyridine N-oxide (205052-95-5)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; for 16h; Heating;

DOI:10.1002/1099-0690(200105)2001:10<1853::aid-ejoc1853>3.0.co;2-s

Reference yield:

[2,2]bipyridinyl (366-18-7) → 6-bromo-2,2'-bipyridine N-oxide (205052-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 79 percent / m-CPBA / CHCl₃ / 13 h / 25 °C

2.1: LDA / hexane; tetrahydrofuran / 0.5 h / -70 °C

2.2: 70 percent / BrCN / hexane; tetrahydrofuran / 0.25 h / -70 °C

With 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane; chloroform; 1.1: Oxidation / 2.1: Metallation / 2.2: Bromination;

DOI:10.1021/jo972022i

upstream raw materials:

2,2'-bipyridyl N-oxide

2,6-dibromopyridin N-oxide

2-tri-n-butylstannylpyridine

[2,2]bipyridinyl

Downstream raw materials:

6-[bis(phenylthio)methyl]-4-methoxy-2,2'-bipyridine

6-bromo-4-methoxy-2,2'-bipyridine

collismycin A

6-bromo-4-nitro-2,2'-bipyridine N-oxide