3-FORMYL-1H-INDOLE-6-CARBONITRILE Chemical Properties

Boiling point:

429.6±25.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

pka

13.67±0.30(Predicted)

Appearance

Light yellow to yellow Solid

InChI

1S/C10H6N2O/c11-4-7-1-2-9-8(6-13)5-12-10(9)3-7/h1-3,5-6,12H

InChIKey

KCNWLZZKKCXGOC-UHFFFAOYSA-N

SMILES

N#CC1=CC2=C(C=C1)C(C=O)=CN2

Safety Information

HS Code 

2933998090

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

3-FORMYL-1H-INDOLE-6-CARBONITRILE Usage And Synthesis

Synthesis

a) Synthesis of 3-formyl-1H-indole-6-carbonitrile: Under stirring conditions, phosphorus oxychloride (POCl3, 0.593 g, 3.87 mmol) was slowly added dropwise to 5 mL of N,N-dimethylformamide (DMF). After stirring for 10 min, 6-cyanoindole (1H-indole-6-carbonitrile, 0.500 g, 3.52 mmol) was added in batches. The reaction mixture was stirred at room temperature for 1 hour, followed by warming up to 40°C and continued stirring for 1 hour. Upon completion of the reaction, the mixture was poured into ice water and adjusted to alkaline with aqueous sodium hydroxide. The mixture was then heated to 100 °C for 1 min, cooled again in an ice bath and extracted three times with ethyl acetate (EtOAc). The organic layers were combined, washed with water, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was recrystallized by water-ethanol mixed solvent to give the target product 3-formyl-1H-indole-6-carbonitrile 0.379 g in 63% yield. The product was characterized by 1H NMR (500 MHz, MeOH-d4): δ 9.98 (s, 1H), 8.33 (s, 1H), 8.31 (d, 1H), 7.89 (m, 1H), 7.52 (m, 1H).

References

[1] Patent: WO2005/66132, 2005, A1. Location in patent: Page/Page column 67
[2] Journal of Medicinal Chemistry, 1983, vol. 26, # 2, p. 294 - 298
[3] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 1, p. 81 - 86
[4] Journal of Medicinal Chemistry, 1997, vol. 40, # 18, p. 2843 - 2857
[5] Patent: WO2009/153307, 2009, A1. Location in patent: Page/Page column 38-39