10273-88-8

Basic information

• Product Name: 3-methyl-2,2'-bipyridine
• Synonyms: 3-methyl-2,2'-bipyridine;3-Methyl-[2,2']bipyridinyl
• CAS NO: 10273-88-8
• Molecular Formula: C₁₁H₁₀N₂
• Molecular Weight: 170
• Mol File: 10273-88-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 282.1±25.0 °C(Predicted)
• Appearance: /
• Density: 1.081±0.06 g/cm3(Predicted)
• PKA: 4.39±0.20(Predicted)
• CAS DataBase Reference: 3-methyl-2,2'-bipyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl-2,2'-bipyridine(10273-88-8)
• EPA Substance Registry System: 3-methyl-2,2'-bipyridine(10273-88-8)

Safety Data

• Hazardous Substances Data: 10273-88-8(Hazardous Substances Data)

Upstream product

• 1620-75-3 2-Cyano-6-methylpyridine 
• 131543-46-9 Glyoxal 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 3430-17-9 2-bromo-3-picoline 
• 882521-96-2 pyridine-2-boronic acid N-phenyldiethanolamine ester 
• 51954-54-2 2-(p-tolylthio)pyridine 
• 109-04-6 2-bromo-pyridine 

Downstream Products

• 1518913-10-4 C₂₀H₁₉BN₂ 
• 1518913-03-5 C₂₉H₃₁BN₂ 

Relevant articles and documents

Synthesis of 2,2-Bipyridines via Suzuki-Miyaura Cross-Coupling

For a long time, the Suzuki-Miyaura cross-coupling reaction could not be used for the synthesis of 2,2′-bipyridines due to the lack of sufficiently stable 2-pyridylboron compounds. Stabilized 2-pyridylboronic acid esters recently developed by Hodgson, however, were found to be ideally suited for this purpose. Two general protocols could be developed and demonstrated to be valuable alternatives, which can be used very efficiently for the synthesis of functionalized 2,2-bipyridines.

Rollover-assisted C(sp2)-C(sp3) bond formation

Rollover cyclometalation involves bidentate heterocyclic donors, unusually acting as cyclometalated ligands. The resulting products, possessing a free donor atom, react differently from the classical cyclometalated complexes. Taking advantage of a rollover / retro-rollover reaction sequence, a succession of oxidative addition and reductive elimination in a series of platinum(II) complexes [Pt(N,C)(Me)(PR3)] resulted in a rare C(sp2)-C(sp3) bond formation to give the bidentate nitrogen ligands 3-methyl-2,2′-bipyridine, 3,6-dimethyl-2,2′- bipyridine, and 3-methyl-2-(2′-pyridyl)-quinoline, which were isolated and characterized. The nature of the phosphane PR3 is essential to the outcome of the reaction. This route constitutes a new method for the activation and functionalization of C-H bond in the C(3) position of bidentate heterocyclic compounds, a position usually difficult to functionalize. Rock and rollover! Rare cases of C(sp2)-C(sp3) bond formation from Pt IV cyclometalated complexes are described, through a succession of oxidative addition and reductive elimination reactions, taking advantage of a rollover / retro-rollover sequence (see scheme).

Rapid and efficient synthesis of functionalized bipyridines

The Negishi reaction affords a mild and efficient method to convert chloro- and bromo-pyridines into functionalized 2,2′-bi-pyridines using commercially available starting materials. This method also extends to the conversion of dibromopyridines to 5- and 6-bromobipyridines, which are powerful synthons for incorporation into larger supramolecular systems.