ChemicalBook CAS DataBase List 4-phenylnicotinonitrile

4-phenylnicotinonitrile synthesis

8synthesis methods

Product Name:4-phenylnicotinonitrile
CAS Number:39065-51-5
Molecular formula:C12H8N2
Molecular Weight:180.21

100-54-9 Synthesis

100-54-9
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$5.00/10g

98-80-6 Synthesis

98-80-6
746 suppliers
$5.00/5g

39065-49-1 Synthesis

39065-49-1
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39065-51-5
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39065-54-8 Synthesis

6-PHENYLNICOTINONITRILE 97+%3-CYANO-6-PHENYLPIRIDINE

39065-54-8
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$32.00/100mg

Yield:39065-49-1 21 mg ，39065-54-8 30 mg ，39065-51-5 16 mg

Reaction Conditions:

with ammonium peroxodisulfate;zinc trifluoromethanesulfonate;silver nitrate in dichloromethane;water at 20; for 4 h;Overall yield = 67 %; regioselective reaction;Minisci Aromatic Substitution;

Steps:

General procedure: Ammonium persulfate (3 equiv, 342 mg), phenylboronic acid (1.5 equiv, 91 mg), silver nitrate (0.2 equiv, 17 mg), and zinc trifluoromethanesulfonate (0.2 equiv, 36 mg) were combined ina 10 mL round bottom flask. A heterocycle (1 equiv, 0.5 mmol) was then added to the same flask and solvated with water (0.4 mL) and CH₂Cl₂ (1.6 mL). The resulting mixture was sonicated for 10 sec and placed on a stir plate to stir vigorously at room temperature for 4 h. The reaction was quenched with 28% ammonium hydroxide (2 mL), diluted with water (10 mL), and extracted with CH₂Cl₂ (3 x 10 mL). The organic layer was dried over sodium sulfate, filtered through cotton, and evaporated en vacuo. The products were purified by column chromatography (SiO₂, 5-20% EtOAc/hexanes). Products 3b, 3c, and 3d required further purification by crystallization as the trifluoromethanesulfonic acid salts and recrystallization from THF/hexanes.

References:

Biaco, Joyce L.;Jones, Savannah L.;Barker, Timothy J. [Heterocycles,2016,vol. 92,# 9,p. 1687 - 1697]

939-23-1 Synthesis