4-METHYL-2,2'-BIPYRIDINE Chemical Properties

Melting point:

62-64 °C(Solv: ligroine (8032-32-4))

Boiling point:

296.6±25.0 °C(Predicted)

Density 

1.081±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.73±0.18(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C11H10N2/c1-9-5-7-13-11(8-9)10-4-2-3-6-12-10/h2-8H,1H3

InChIKey

OHSRAWAUPZWNKY-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

9999999999

4-METHYL-2,2'-BIPYRIDINE Usage And Synthesis

Uses

4-Methyl-2,2'-bipyridine is a useful compound for research.

Synthesis

Example 2 Synthesis of 4-methyl-2-(2'-pyridinyl)pyridine: Tetrahydrofuran (10 ml) and isopropylmagnesium chloride (2.0 M, 7.7 ml, 15.5 mmol) were added to a 50 ml flask under nitrogen protection. Subsequently, a solution prepared from 2-bromopyridine (2.45 g, 15.5 mmol) dissolved in tetrahydrofuran (3 ml) was added slowly and dropwise over 10 min. The reaction mixture was stirred for 1 hour and then a solution prepared from 4-methyl-2-benzenesulfonylpyridine (3.00 g, 12.9 mmol) dissolved in tetrahydrofuran (5 ml) was added dropwise over 10 minutes. The reaction mixture was continued to be stirred at room temperature for 5 h. Isopropanol (1 ml) was added at the termination of the reaction. The reaction mixture was poured into water and extracted with ethyl acetate (15 ml x 2). The organic phases were combined, concentrated and purified by silica gel column chromatography to afford the target product 4-methyl-2,2'-bipyridine (1.51 g, 89% yield, based on 4-methyl-2-phenylsulfonylpyridine) as a white solid. The product was characterized by 1H-NMR (CDCl3): δ 2.36 (s, 3H), 7.06 (d, 1H, J = 5.0 Hz), 7.20-7.25 (m, 1H), 7.69-7.74 (m, 1H), 8.16 (s, 1H), 8.32 (d, 1H, J = 8.0 Hz), 8.46 (d, 1H, J = 4.6 Hz) , 8.57-8.63 (m, 1H).

References

[1] Patent: EP1548005, 2005, A1. Location in patent: Page/Page column 11

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