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

4,4'-Di-tert-butyl-2,2'-bipyridine

Catalog Number: EVT-1637421
CAS Number: 72914-19-3
Molecular Formula: C18H24N2
Molecular Weight: 268.4 g/mol
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Product Introduction

Description
4,4’-Di-tert-butyl-2,2’-bipyridine is a white crystalline compound . It is used as a ligand in chemical reactions and is an efficient reagent for the oxidation of primary and secondary alcohols to carbonyl compounds . It also enables nickel-catalyzed cross-electrophile couplings of diverse aryl and alkyl halides .

Synthesis Analysis

The compound can be synthesized from the reaction of MoO2Cl2(tbbpy) in water under microwave-assisted heating at 120 °C for 4 hours . It can also be prepared from 4-(tert-butyl)-2-(tert-butyl-dimethylsilyl)pyridine and 2-bromo-4-(tert-butyl)pyridine through a Hiyama-Denmark cross-coupling reaction .

Molecular Structure Analysis

The structure of the oxodiperoxo complex MoO(O2)2(tbbpy) (tbbpy = 4,4’-di-tert-butyl-2,2’-bipyridine) was determined by single crystal X-ray diffraction .

Chemical Reactions Analysis

4,4’-Di-tert-butyl-2,2’-bipyridine acts as a ligand in various chemical reactions . It is used in the synthesis of oxidovanadium (IV) complex [VOCl2(dbbpy)(H2O)], which is used as a catalyst for the epoxidation of cyclooctene in the presence of tert-butyl hydroperoxide .

Physical And Chemical Properties Analysis

4,4’-Di-tert-butyl-2,2’-bipyridine is a white to almost white powder or crystal . Its melting point ranges from 159.0 to 163.0 °C .

Properties

CAS Number

72914-19-3

Product Name

4,4'-Di-tert-butyl-2,2'-bipyridine

IUPAC Name

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

Molecular Formula

C18H24N2

Molecular Weight

268.4 g/mol

InChI

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

InChI Key

TXNLQUKVUJITMX-UHFFFAOYSA-N

SMILES

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

Canonical SMILES

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

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