5-CHLORO-2,3-DIPHENYL-1H-INDOLE Chemical Properties

Melting point:

130-131 °C(Solv: ethanol (64-17-5))

Boiling point:

478.1±33.0 °C(Predicted)

Density 

1.243±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

15.63±0.30(Predicted)

Appearance

Light brown to brown Solid

InChI

InChI=1S/C20H14ClN/c21-16-11-12-18-17(13-16)19(14-7-3-1-4-8-14)20(22-18)15-9-5-2-6-10-15/h1-13,22H

InChIKey

BAEWCDBRAIDXMN-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(Cl)C=C2)C(C2=CC=CC=C2)=C1C1=CC=CC=C1

5-CHLORO-2,3-DIPHENYL-1H-INDOLE Usage And Synthesis

Synthesis

4-Chloroaniline (76.5 mg, 0.6 mmol) and diphenylacetylene (71.3 mg, 0.4 mmol) were used as raw materials, and Cp*Rh(H2O)3(OTf)2 (11.8 mg, 5 mol%) was added to the reaction vials as a catalyst, acetic anhydride (59.0 μL, 0.6 mmol) as acylate, and 2.0 mL of tertiary amyl alcohol as the solvent. The reaction system was stirred at 100 °C for 24 h under oxygen atmosphere (1 atm). After completion of the reaction, NaOH (48 mg, 1.2 mmol) and methanol (2 mL) were added to the reaction mixture and stirring was continued for 2 hours. Subsequently, purification by column chromatography afforded the target compound 5-chloro-2,3-diphenyl-1H-indole (3ja) as a white solid in 90% yield.

References

[1] Chemical Communications, 2014, vol. 50, # 33, p. 4331 - 4334
[2] Patent: CN105218426, 2016, A. Location in patent: Paragraph 0039; 0040