CAS 72914-19-3 4,4'-Di-tert-butyl-2,2'-bipyridine

Synonyms

BBBPY; 4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridine

IUPAC Name

4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridine

Molecular Weight

268.40

Molecular Formula

C18H24N2

Canonical SMILES

CC(C)(C)C1=CC(=NC=C1)C2=NC=CC(=C2)C(C)(C)C

InChI

TXNLQUKVUJITMX-UHFFFAOYSA-N

InChI Key

InChI=1S/C18H24N2/c1-17(2,3)13-7-9-19-15(11-13)16-12-14(8-10-20-16)18(4,5)6/h7-12H,1-6H3

Boiling Point

395.4±42.0 °C(Predicted)

Melting Point

159-161 °C-lit.

Purity

98%

Appearance

White solid

Complexity

278

Covalently-Bonded Unit Count

Exact Mass

268.193948774

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

268.193948774

Rotatable Bond Count

Topological Polar Surface Area

25.8 Å²

Application

4,4'-Di-tert-butyl-2,2'-bipyridine is a versatile white crystalline powder that serves as a critical reagent in the scientific realm, notable for its role in the synthesis and study of apoptotic ruthenium nitrogen heterocyclic complexes, which exhibit antiproliferative and cytotoxic properties. This compound is extensively utilized as a ligand across various catalytic processes, including the iridium-catalyzed borylation of arenes, synthesis of arylboronic acids and aryl trifluoroborates, silyl-directed ortho-borylation, and microwave-accelerated borylation of aromatic C-H bonds. It also participates in iridium-catalyzed meta borylation and subsequent halogenation of disubstituted arenes, as well as silane borylation with subsequent aryl borylation. Further applications include its use in nickel-catalyzed hydroxycarboxylation of dienes, synthesis of functionalized dialkyl ketones from carboxylic acids and alkyl halides, and the iron-catalyzed arylation of heterocycles, illustrating 4,4'-Di-tert-butyl-2,2'-bipyridine's integral role in modern synthetic and catalytic chemistry.

February 17, 2025

Excellent Research Reagent for Complex Syntheses

As a ligand, 4,4'-Di-tert-butyl-2,2'-bipyridine significantly enhanced our iridium-catalyzed borylation processes. This white crystalline powder reliably supported complex syntheses, streamlining our workflow in producing various functionalized molecules.