ChemicalBook CAS DataBase List 1-phenyl-9H-carbazole

1-phenyl-9H-carbazole synthesis

10synthesis methods

Product Name:1-phenyl-9H-carbazole
CAS Number:104636-53-5
Molecular formula:C18H13N
Molecular Weight:243.3

1H-Carbazole, 2,3,4,9-tetrahydro-1-phenyl-

34177-06-5
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104636-53-5
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Yield:104636-53-5 99%

Reaction Conditions:

with 2,3-dicyano-5,6-dichloro-p-benzoquinone in acetonitrile at 20; for 6 h;

Steps:

1-phenyl-9H-carbazole (8a):

To a solution of THC5a (0.05 g, 0.2 mmol) in dry CH3CN (2 mL) at rt was added DDQ (0.051g, 0.22 mmol) and the reaction was stirred for 6 h at same temperature. After completion of reaction (monitored by TLC), solvent was evaporated and the crude residuewas purified via column chromatography using 10% EtOAc in pet ether as eluent to provide the carbazole 8a (48 mg, 99%) as a white solid. MP:130-132 oC; IR (Neat): max 3433,3057, 2926, 2378, 2345, 1728, 1597, 1496, 1454, 1413, 1317, 1232, 1122, 1062 cm1; 1H NMR (400 MHz, CDCl3):δ 8.31 (brs, 1H), 8.10 (dd, J = 13.6, 7.6 Hz, 2H), 7.70 (d, J = 6.8 Hz, 2H), 7.57 (t, J = 7.2 Hz, 2H), 7.46-7.40 (m, 4H), 7.34 (t, J = 7.6 Hz, 1H), 7.28-7.25 (m, 1H); 13C NMR (100 MHz, CDCl3): 139.4, 139.0, 137.2, 129.2 (3C), 128.4 (3C), 127.5, 125.0, 123.6, 123.5, 120.4, 119.9, 119.5, 119.4,110.7. This data was in good agreement with the literature.4

References:

Nanda, Laxmi Narayan;Rangari, Vipin Ashok [Tetrahedron Letters,2018,vol. 59,# 33,p. 3194 - 3197] Location in patent:supporting information

16807-11-7 Synthesis