5-Bromo-2,3'-bipyridine

Base Information

• Chemical Name: 5-Bromo-2,3'-bipyridine
• CAS No.: 774-53-8
• Molecular Formula: C10H7BrN2
• Molecular Weight: 235.083
• Hs Code.: 2933399090
• European Community (EC) Number: 678-943-8
• DSSTox Substance ID: DTXSID10464417
• Nikkaji Number: J2.960.339A
• Wikidata: Q72452016
• Mol file: 774-53-8.mol

Synonyms:5-BROMO-2,3'-BIPYRIDINE;774-53-8;5-bromo-2-pyridin-3-ylpyridine;5-BROMO-[2,3']-BIPYRIDINE;5-Bromo-[2,3']bipyridinyl;MFCD09037420;2,3'-Bipyridine, 5-bromo-;SCHEMBL999177;DTXSID10464417;ILJRIAPZWHYPMK-UHFFFAOYSA-N;AKOS015941976;BS-2101;CS-0319439

Chemical Property of 5-Bromo-2,3'-bipyridine

Chemical Property:

• Melting Point: 75-78°C
• Boiling Point: 332.4oC at 760 mmHg
• Flash Point: 154.8oC
• PSA: 25.78000
• Density: 1.493g/cm3
• LogP: 2.90610
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 233.97926
• Heavy Atom Count: 13
• Complexity: 163

Purity/Quality:

99%, ^*data from raw suppliers

5-Bromo-2,3'-bipyridine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CN=C1)C2=NC=C(C=C2)Br

Technology Process of 5-Bromo-2,3'-bipyridine

There total 9 articles about 5-Bromo-2,3'-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: 81.6%

2-iodo-5-bromopyridine (223463-13-6) + 3-pyridylboronic acid (1692-25-7) → 5-bromo-2,3′-bipyridine (774-53-8)

Guidance literature:

2-iodo-5-bromopyridine; 3-pyridylboronic acid; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; for 0.166667h; Inert atmosphere;

With potassium carbonate; In 1,4-dioxane; water; at 100 ℃; for 4h; Inert atmosphere;

Reference yield: 78.0%

2,5-dibromopyridine (624-28-2) + 3-pyridylboronic acid (1692-25-7) → 5-bromo-2,3′-bipyridine (774-53-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; water; at 80 ℃; regioselective reaction; Reflux;

DOI:10.1016/j.tet.2009.04.049

Reference yield: 70.0%

2,5-dibromopyridine (624-28-2) + 3-Diethylboranylpyridine (89878-14-8) → 5-bromo-2,3′-bipyridine (774-53-8)

Guidance literature:

With potassium hydroxide; tetrabutylammomium bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; Heating;

DOI:10.1248/cpb.33.4755

upstream raw materials:

2,5-dibromopyridine

3-Diethylboranylpyridine

3-Bromopyridine

2-iodo-5-bromopyridine

Downstream raw materials:

5-p-tolyl-2,3'-bipyridine

3-(2,3'-bipyridin-5-yl)aniline

5-(4-methoxyphenyl)-2,3'-bipyridine

methyl 4-(2,3'-bipyridin-5-yl)benzoate

Refernces

• 1、 -. "Imidazole derivatives, its pharmaceutical composition and use thereof". Paragraph 0227-0229. . Retrieved 2017/02/24.
• 2、 Jung, Hye-Soo,Kim, Seung-Hoi. "A study on the selectivity of arylzinc reagents in cross-coupling reactions with chemically equivalent and pseudo-equivalent dibromopyridines". supporting information. p. 280 - 282. Retrieved 2014/02/14.