ChemicalBook CAS DataBase List 1,4-Di(4-pyridyl)benzene

1,4-Di(4-pyridyl)benzene synthesis

10synthesis methods

Product Name:1,4-Di(4-pyridyl)benzene
CAS Number:113682-56-7
Molecular formula:C16H12N2
Molecular Weight:232.28

Pyridylboronic pinacol ester (3.64 g, 17.8 mmol), 1,4-dibromobenzene (1.40 g, 5.92 mmol), and Cs2CO3(11.6 g, 35.5 mmol) were added to a 1:1 mixture of dry PhMe/DMF (300 mL), which had been degassed with Ar for 15 min. Next, Pd(PPh3)4(0.68 g, 0.59 mmol) was added to the reaction mixture, and the solution was heated to 130° C. under Ar for 48 h. Then, the reaction mixture was cooled to room temperature, and the palladium catalyst was filtered off using Celite. The organic phase was concentrated under a vacuum and then dissolved, CH2Cl2, followed by extraction with H2O three times. The organic layer was made acidic (pH 2-3) by adding dropwise concentrated HCl, which caused the desired product to precipitate. The precipitate was collected by filtration and then dissolved in H2O. Finally, aq. NaOH (10 M) was added dropwise to the water layer until the pH was 8-9, which resulted in the precipitation of pure product ExBIPY (973 mg, 71 percent) as a white solid.

1120-87-2 Synthesis

1120-87-2
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4612-26-4 Synthesis

4612-26-4
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113682-56-7
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$20.00/100mg

Yield:113682-56-7 90%

Reaction Conditions:

with C₃₇H₄₅ClN₂O₃PPd;potassium carbonate in ethanol;water at 80; for 6 h;Inert atmosphere;Schlenk technique;Suzuki Coupling;

Steps:

General procedure for Suzuki coupling reactions
A 10-mL round-bottom flask was charged with the prescribe damount of catalyst, 1,4-benzenediboronic acid (0.5 mmol), N-heteroaryl halides (1.5 mmol), the selected base (1.5 mmol) and solvent (4 mL). The flask was placed in an oil bath and heated at 80 °C for 6 h, then cooled to room temperature and extracted with CH₂Cl₂. The crude products obtained from evaporation were purified by flash chromatography on silica gel. The products 5b-c, 5f, 5m [21], 5d [22], 5e [23], 5l [24] were known compounds and characterized by the comparison of data with those in the literature. The products 5a, 5g-k, 5n-o were new compounds and characterized by elemental analysis, IR, MS,¹H and ¹³C NMR.

References:

Xiao, Zhi-Qiang;Xu, Chen;Li, Hong-Mei;Han, Xin;Wang, Zhi-Qiang;Fu, Wei-Jun;Hao, Xin-Qi;Song, Mao-Ping [Transition Metal Chemistry,2015,vol. 40,# 5,art. no. 9942,p. 501 - 508]

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106-37-6 Synthesis