3-(1H-INDOL-3-YL)-3-OXO-PROPIONITRILE Chemical Properties

Melting point:

241°C

Boiling point:

447.2±25.0 °C(Predicted)

Density 

1.285±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

soluble in Dimethylformamide

form 

Solid

pka

8.39±0.30(Predicted)

color 

White to Light yellow to Light orange

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

25-36

Safety Statements 

26-45

RIDADR 

UN 3439 6.1/PG III

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

2933998090

3-(1H-INDOL-3-YL)-3-OXO-PROPIONITRILE Usage And Synthesis

Chemical Properties

Solid

Uses

3-Cyanoacetylindole (cas# 20356-45-0) is a compound useful in organic synthesis.

Synthesis

GENERAL METHOD: Cyanoacetic acid (0.363 g, 4.26 mmol) was dissolved in acetic anhydride (8 mL), stirred and heated to 50 °C until the solid was completely dissolved. Indole (0.5 g, 4.26 mmol) was then added and the reaction mixture was heated to 85°C and maintained for 5 minutes. Upon completion of the reaction, the mixture was cooled to 0 °C and the precipitate was collected by diafiltration and washed with ice-cold methanol (2 x 5 mL) to afford 3-(1H-indol-3-yl)-3-oxopropanenitrile in 76% yield. Next, an ethanol solution (10 mL) of 3-oxo-3-(1H-indol-3-yl)propionitrile (1.08 mmol) was mixed with an ethanol solution (10 mL) of 4-chlorobenzaldehyde (1.14 mmol) and heated to 70 °C. Piperidine (2 drops) was then added and heating was continued to reflux for 2 hours. At the end of the reaction, the mixture was cooled and the solvent was removed under reduced pressure to give a yellow solid. The crude product was purified by ethanol recrystallization to give the target compound (14) as a yellow solid in 80% yield with a melting point of 230-232 °C.

References

[1] Journal of Heterocyclic Chemistry, 2007, vol. 44, # 1, p. 109 - 114
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 6, p. 810 - 813
[3] Synthesis, 2004, # 16, p. 2760 - 2765
[4] Patent: WO2008/87529, 2008, A1. Location in patent: Page/Page column 126
[5] Patent: CN107698565, 2018, A. Location in patent: Paragraph 0037; 0038

3-(1H-INDOL-3-YL)-3-OXO-PROPIONITRILE(20356-45-0)Related Product Information

• 3-(4-methyl-1H-indol-3-yl)-3-oxopropanenitrile
• 3-(5-METHOXY-1H-INDOL-3-YL)-3-OXOPROPANENITRILE
• 3-(2-METHYL-1H-INDOL-3-YL)-3-OXO-PROPIONITRILE
• 3-(7-ethyl-1H-indol-3-yl)-3-oxopropanenitrile
• 3-(5-BROMOINDOL-3-YL)-3-OXOPROPANENITRILE
• 3-(5-BENZYLOXYINDOL-3-YL)-3-OXOPROPANENITRILE
• 3-(CYANOACETYL)-1-METHYLINDOLE
• 3-(1-METHYL-2-PHENYL-1H-INDOL-3-YL)-3-OXO-PROPIONITRILE
• 3-(6-fluoro-1H-indol-3-yl)-3-oxopropanenitrile
• 3-(1-ETHYL-2-PHENYL-1H-INDOL-3-YL)-3-OXO-PROPIONITRILE
• 3-(1H-INDOL-3-YL)-3-OXO-PROPIONITRILE