1-PHENYL-1H-INDOLE Chemical Properties

Melting point:

60-62℃

Boiling point:

190°C/20mmHg(lit.)

Density 

1.05±0.1 g/cm3 (20 ºC 760 Torr)

refractive index 

1.6580 to 1.6620

storage temp. 

Store at room temperature

form 

clear liquid

color 

Colorless to Yellow to Orange

InChI

InChI=1S/C14H11N/c1-2-7-13(8-3-1)15-11-10-12-6-4-5-9-14(12)15/h1-11H

InChIKey

YBFCBQMICVOSRW-UHFFFAOYSA-N

SMILES

N1(C2=CC=CC=C2)C2=C(C=CC=C2)C=C1

Safety Information

HS Code 

2933.99.8290

1-PHENYL-1H-INDOLE Usage And Synthesis

Synthesis

1. indole (11.7 g, 0.1 mol) and bromobenzene (117 mL) were added to a four-necked flask, stirred and heated to 150-160°C for reflux. 2. cuprous chloride (2.47 g, 0.025 mol), L-proline (5.75 g, 0.05 mol) and potassium hydroxide (11.22 g, 0.2 mol) were added sequentially and the reaction was carried out for 8-12 h. The progress of the reaction was monitored by TLC. 3. After completion of the reaction, it was slightly cooled, the reaction mixture was filtered, the brown solid was washed with water, and the insoluble material cuprous chloride was dried and recycled. 4. The organic layer of the filtrate is washed with water and the bromobenzene is subsequently recovered by vacuum distillation. 5. 5. Finally, 1-phenylindole (17.76 g, 92.02% yield) was purified by distillation under reduced pressure.

References

[1] Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7729 - 7737
[2] Tetrahedron Letters, 2000, vol. 41, # 4, p. 481 - 483
[3] Tetrahedron Letters, 2017, vol. 58, # 32, p. 3155 - 3159
[4] New Journal of Chemistry, 2018, vol. 42, # 4, p. 2782 - 2789
[5] Comptes Rendus Chimie, 2018, vol. 21, # 7, p. 659 - 668

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