Description
4,4'-Vinylenedipyridine belongs to dipyridine derivatives. It is used as a ligand in coordination chemistry for the preparation of a variety of organic compounds. It has also been used as a catalyst in polymer synthesis and as a reagent in peptide and peptidomimetic synthesis.
Chemical Properties
LIGHT BROWN CRYSTALLINE POWDER
Uses
4,4''-Vinylenedipyridine (cas# 13362-78-2) is a compound useful in organic synthesis.
Synthesis
The general procedure for the synthesis of 1,2-bis(4-pyridyl)ethene from 4-methylpyridine and 4-pyridinecarboxaldehyde was as follows: 400 μL (4.12 mmol) of 4-methylpyridine was reacted with 3.0 mL (4.32 mmol) of a solution of LDA in THF (5 mL) at -70 °C. Under light-avoiding conditions, 465 μL (4.12 mmol) of 4-pyridinecarboxaldehyde was added by continuous stirring and slow dropwise addition. Subsequently, the reaction mixture was refluxed in the presence of 10 mL of acetic acid for 24 h. The reaction mixture was observed to transform into a yellow solution. The light yellow solid product was isolated from this solution by rotary evaporation. Purification of the solid product using column chromatography under similar conditions afforded 368 mg (49% yield) of the target compound.1H NMR (400 MHz, CDCl3, δ): 8.62 (d, J = 4Hz, 4H, Ar-H), 7.61 (d, J = 4Hz, 4H, Ar-H), 7.55 (s, 2H, -CH=CH-).
Purification Methods
Crystallise the ethylene from water (1.6g/100mL at 100o). The di-hydrochloride has m 347o, from EtOH. [Beilstein 23/8 V 239.]
References
[1] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2017, vol. 183, p. 45 - 52
[2] Journal of the American Chemical Society, 1948, vol. 70, p. 2330,2333
