4,4'-Vinylenedipyridine Chemical Properties

Melting point:

148-152 °C (lit.)

Boiling point:

334.1±11.0 °C(Predicted)

Density 

1.145±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

5.50±0.26(Predicted)

color 

Brown to Dark Brown

BRN 

3865

InChI

InChI=1S/C12H10N2/c1(11-3-7-13-8-4-11)2-12-5-9-14-10-6-12/h1-10H/b2-1+

InChIKey

MGFJDEHFNMWYBD-UPHRSURJSA-N

SMILES

C(/C1=CC=NC=C1)=C\C1=CC=NC=C1

CAS DataBase Reference

13362-78-2(CAS DataBase Reference)

NIST Chemistry Reference

Pyridine, 4,4'-(1,2-ethenediyl)bis-, (E)-(13362-78-2)

EPA Substance Registry System

trans-1,2-Bis(4-pyridyl)ethene (13362-78-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

HS Code 

29333990

MSDS

• Language:English Provider:4,4'-Vinylenedipyridine
• Language:English Provider:SigmaAldrich

4,4'-Vinylenedipyridine Usage And Synthesis

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

suzuki reaction

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

4,4'-Vinylenedipyridine(13362-78-2)Related Product Information

• CHLORODIMETHYLVINYLSILANE
• ETHYLENE OXIDE
• VINYL PROPIONATE
• ETHYLENE
• POLY(4-VINYLPYRIDINE)
• Ethylene glycol
• 4-(4-CHLORO-BENZYLOXY)-PHENYLAMINE
• Polyethylene
• trans,trans-2,4-Undecadienal
• Ethyleneimine
• Vinyl resin
• 2,2'-VINYLENEDIPYRIDINE
• 2,2'-VINYLENEDIPYRIDINE
• trans-2,4-vinylenedipyridine
• 4,4'-Vinylenedipyridine
• 4,4'-vinylenedipyridine bis(2,2'-6,2''-terpyridineplatinum(II))
• TRANSFAT
• Ethyleneamines