11,12-Dihydro-11-phenylindolo[2,3-a]carbazole Chemical Properties

Boiling point:

598.8±32.0 °C(Predicted)

Density 

1.26

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

16.78±0.30(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C24H16N2/c1-2-8-16(9-3-1)26-22-13-7-5-11-18(22)20-15-14-19-17-10-4-6-12-21(17)25-23(19)24(20)26/h1-15,25H

InChIKey

IENOQUQIVSMWGP-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC=C2)C2=C1C1N(C3=CC=CC=C3)C3=C(C=1C=C2)C=CC=C3

CAS DataBase Reference

1024598-06-8

Safety Information

HS Code 

2933.99.8290

11,12-Dihydro-11-phenylindolo[2,3-a]carbazole Usage And Synthesis

Synthesis

General procedure for the synthesis of 11,12-dihydro-11-phenylindolo[2,3-a]carbazole from bromobenzene and 11,12-dihydroindolo[2,3-a]carbazole: Pd2(dba)3 (178.6 mg, 0.20 mmol) and t-Bu3P (78.9 mg, 0.39 mmol) were mixed with Pd2(dba)3 (178.6 mg, 0.20 mmol) and t-Bu3P (78.9 mg, 0.39 mmol) in o-xylene (50 mL) at room temperature under stirred for 10 min. Subsequently, 11,12-dihydroindolo[2,3-a]carbazole (Intermediate I-1, 5 g, 19.51 mmol), bromobenzene (3.37 g, 21.46 mmol), and t-BuONa (1.12 g, 11.71 mmol) were added and stirred at reflux for 48 hours at 160 °C. After completion of the reaction, it was cooled to room temperature, distilled water (20 mL) was added and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and the solvent evaporated. Purification by column chromatography afforded 11,12-dihydro-11-phenylindolo[2,3-a]carbazole (Intermediate I-2, 5.35 g, 83% yield).MS-EI, m/e: 332.13 (calculated), 332.19 (measured).

References

[1] Patent: KR2015/96018, 2015, A. Location in patent: Paragraph 0377-0379
[2] Patent: US2018/90690, 2018, A1. Location in patent: Paragraph 0161; 0162
[3] Patent: KR2018/32519, 2018, A. Location in patent: Paragraph 0120-0122
[4] Patent: EP2894157, 2015, A1. Location in patent: Paragraph 0198
[5] Patent: KR2015/84657, 2015, A. Location in patent: Paragraph 1642-1645

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