ChemicalBook CAS DataBase List 1,4-DIPHENYLBUTADIYNE

1,4-DIPHENYLBUTADIYNE synthesis

12synthesis methods

Product Name:1,4-DIPHENYLBUTADIYNE
CAS Number:886-66-8
Molecular formula:C16H10
Molecular Weight:202.25

536-74-3 Synthesis

536-74-3
294 suppliers
$10.00/1g

768-60-5
217 suppliers
$6.00/1g

886-66-8
132 suppliers
$24.00/1g

Benzene, 1-methoxy-4-(4-phenyl-1,3-butadiyn-1-yl)-

23429-36-9
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inquiry

Benzene, 1,1'-(1,3-butadiyne-1,4-diyl)bis[4-methoxy-

22779-05-1
3 suppliers
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Yield:23429-36-9 92% ，886-66-8 6% ，22779-05-1 24%

Reaction Conditions:

with copper(II) choride dihydrate;N,N,N,N,-tetramethylethylenediamine;Pd(NH₃)₄Cl₂·H₂O;oxygen in carbon dioxide at 50; under 67506.8 Torr; for 5 h;Autoclave;Supercritical conditions;liquid CO₂;Reagent/catalyst;Concentration;

Steps:

1 Typical procedure for cross-coupling in ScCO2

A 15-mL autoclave equipped with a magnetic stirrer was charged with phenylacetylene (55μL, 0.5mmol), 4-methoxyphenylacetylene (130μL, 1mmol), Pd(NH₃)₄Cl₂·H₂O (13mg, 0.05mmol), CuCl₂·2H₂O (10mg, 0.05mmol), TMEDA (54μl, 0.6mmol). Oxygen gas was transferred into the autoclave to a pressure of 1MPa and was later pressurized at room temperature with CO₂ to 9MPa. The reaction mixture was stirred at 50°C for 4h. The agitation rate was fixed at 600rpm. After the reaction was complete, the system was allowed to cool to room temperature, and CO₂ was vented carefully. The residues were dissolved in dichloromethane, then the solution was washed with water. The organic phase was dried over anhydrous MgSO₄, and the solvent was removed under vacuum. The crude products were purified via chromatography on a silica gel column (eluting with a petroleum ether/ethyl acetate mixture, 50/1, v/v) and recrystallized in solution (a mixture of hexane and dichloromethane).

References:

Wang, Yunlong;Suo, Quanling;Han, Limin;Guo, Linlin;Wang, Yaqi;Li, Fawang [Tetrahedron,2018,vol. 74,# 15,p. 1918 - 1925] Location in patent:supporting information

624-31-7 Synthesis