5-Acetylindole Chemical Properties

Melting point:

95-96°C

Boiling point:

284.68°C (rough estimate)

Density 

1.1202 (rough estimate)

refractive index 

1.5460 (estimate)

storage temp. 

Sealed in dry,Room Temperature

pka

16.06±0.30(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C10H9NO/c1-7(12)8-2-3-10-9(6-8)4-5-11-10/h2-6,11H,1H3

InChIKey

GOFIUEUUROFVMA-UHFFFAOYSA-N

SMILES

C(=O)(C1C=CC2=C(C=1)C=CN2)C

CAS DataBase Reference

53330-94-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

2933998090

5-Acetylindole Usage And Synthesis

Uses

5-Acetylindole, is a building block used in various chemical synthesis.

Synthesis

Methyl lithium (1.6 M ether solution, 30 mL, 51.2 mmol) was added slowly and dropwise to a solution of anhydrous tetrahydrofuran (30 mL) of indole-5-carboxylic acid (2.5 g, 15.5 mmol) at 0 °C and under nitrogen protection. The reaction mixture was stirred at room temperature for 4 hours before the reaction was quenched with aqueous ammonium chloride solution and extracted with dichloromethane (3 x 50 mL). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 5-acetylindole (1.8 g, white solid).

References

[1] European Journal of Medicinal Chemistry, 2019, p. 428 - 442
[2] Patent: WO2005/26175, 2005, A1. Location in patent: Page/Page column 73
[3] Patent: EP2287173, 2011, A1. Location in patent: Page/Page column 40-41

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