4,4'-Bis(trifluoromethyl)-2,2'-bipyridine

Base Information

• Chemical Name: 4,4'-Bis(trifluoromethyl)-2,2'-bipyridine
• CAS No.: 142946-79-0
• Molecular Formula: C12H6F6N2
• Molecular Weight: 292.183
• DSSTox Substance ID: DTXSID80476648
• Nikkaji Number: J1.376.940K
• Mol file: 142946-79-0.mol

Synonyms:142946-79-0;4,4'-bis(trifluoromethyl)-2,2'-bipyridine;2,2'-Bipyridine, 4,4'-bis(trifluoromethyl)-;4,4'-Bis(trifluoromethyl)-2,2'-bipyridyl;4-(trifluoromethyl)-2-[4-(trifluoromethyl)pyridin-2-yl]pyridine;MFCD00233878;4,4'-tfmbpy;YSWG806;SCHEMBL810884;DTXSID80476648;FFOMEQIMPYKURW-UHFFFAOYSA-N;AKOS037646020;AS-65838;SY234352;B5463;CS-0081529;T70279;4,4 inverted exclamation mark -Bis(trifluoromethyl)-2,2 inverted exclamation mark -bipyridine

Chemical Property of 4,4'-Bis(trifluoromethyl)-2,2'-bipyridine

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 1
• Exact Mass: 292.04351717
• Heavy Atom Count: 20
• Complexity: 295

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN=C(C=C1C(F)(F)F)C2=NC=CC(=C2)C(F)(F)F
• General Description: 2,2'-Bipyridine, 4,4'-bis(trifluoromethyl)-, also referred to as **btfmb**, is a fluorinated bipyridine derivative that serves as an electron-deficient ligand in coordination chemistry, particularly in ruthenium polypyridyl complexes. Its strong electron-withdrawing trifluoromethyl groups influence the photophysical and redox properties of resulting metal complexes, making them useful in applications such as photoacids, photobases, and panchromatic dyes. Studies have shown that btfmb-containing complexes exhibit unique excited-state dynamics, including longer-lived emission states, and can undergo photoacidic behavior due to localized charge-transfer interactions. Additionally, its synthesis has been optimized via nickel-catalyzed homocoupling reactions for improved yields.

Technology Process of 4,4'-Bis(trifluoromethyl)-2,2'-bipyridine

There total 5 articles about 4,4'-Bis(trifluoromethyl)-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: 93.0%

2-bromo-4-(trifluoromethyl)pyridine (175205-81-9) → 4,4′-bis-(trifluoromethyl)-2,2′-bipyridine (142946-79-0)

Guidance literature:

With palladium diacetate; tetra-(n-butyl)ammonium iodide; potassium carbonate; In N,N-dimethyl-formamide; isopropyl alcohol; at 100 ℃; for 20h; Inert atmosphere;

DOI:10.1021/jacs.9b08746

Reference yield: 89.0%

2-chloro-4-trifluoromethyl pyridine (81565-18-6) → 4,4′-bis-(trifluoromethyl)-2,2′-bipyridine (142946-79-0)

Guidance literature:

With nickel(II) chloride hexahydrate; triphenylphosphine; zinc; In N,N-dimethyl-formamide; at 80 ℃; for 72h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

DOI:10.1016/j.tetlet.2016.04.023

Reference yield: 89.0%

2-iodo-4-(trifluoromethyl)pyridine (326894-74-0) → 4,4′-bis-(trifluoromethyl)-2,2′-bipyridine (142946-79-0)

Guidance literature:

With palladium diacetate; potassium carbonate; In N,N-dimethyl-formamide; isopropyl alcohol; at 100 ℃;

DOI:10.3762/bjoc.11.9

upstream raw materials:

2-chloro-4-trifluoromethyl pyridine

2-bromo-4-(trifluoromethyl)pyridine

2-iodo-4-(trifluoromethyl)pyridine

4-trifluoromethylpyridine