ChemicalBook CAS DataBase List 4'-DIMETHYLAMINOPHENYL ACETYLENE

4'-DIMETHYLAMINOPHENYL ACETYLENE synthesis

13synthesis methods

Product Name:4'-DIMETHYLAMINOPHENYL ACETYLENE
CAS Number:17573-94-3
Molecular formula:C10H11N
Molecular Weight:145.2

N N-DIMETHYL-4-[(TRIMETHYLSILYL)ETHYNYL&

40230-97-5
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$173.00/5g

17573-94-3
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$19.00/250mg

Yield: 99%

Reaction Conditions:

with potassium carbonate in methanol at 20; for 3 h;

Steps:

4.3 Typical procedure for the preparation of N-(4-ethynylphenyl)carbazole (5a)
General procedure: 9-[4-{2-(Trimethylsilyl)ethynyl}phenyl]carbazole (4a, 0.68g, 2.7mmol), potassium carbonate (0.42g, 3.0mmol), and methanol (4.0mL) were placed in a flask, and the suspension was stirred at room temperature. After stirring for 3h, the precipitate that was insoluble in the solvent was separated by atmospheric filtration, and the filtrate was poured into saturated aqueous NH₄Cl solution (20mL). The crude product was extracted with AcOEt (20mL) three times and the combined organic layer was washed with brine (once). The organic layer was collected and dried over anhydrous Na₂SO₄, which was separated by filtration. The filtrate was evaporated in vacuo and subjected to silica-gel column chromatography (eluent: hexane/CH₂Cl₂=5/1) to obtain the deprotection product 5a in 99% yield (0.53g, 2.0mmol) as a white solid.

References:

Yamada, Shigeyuki;Morita, Masato;Konno, Tsutomu [Journal of Fluorine Chemistry,2017,vol. 202,p. 54 - 64]