6-Cyanoindole Chemical Properties

Melting point:

130-132°C

Boiling point:

350.0±15.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Dichloromethane, Methanol

pka

15.17±0.30(Predicted)

form 

Solid

color 

Off-White Crystalline

Sensitive 

Air & Light Sensitive

BRN 

116502

InChI

InChI=1S/C9H6N2/c10-6-7-1-2-8-3-4-11-9(8)5-7/h1-5,11H

InChIKey

SZSZDBFJCQKTRG-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC(C#N)=C2)C=C1

CAS DataBase Reference

15861-36-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-36/37-26

RIDADR 

3439

HazardClass 

6.1

PackingGroup 

III

HS Code 

29339900

MSDS

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6-Cyanoindole Usage And Synthesis

Chemical Properties

Off-White Crystalline Solid

Uses

6-Cyanoindole (cas# 15861-36-6) is a compound useful in organic synthesis.

Synthesis

To a stirred solution of 4-methyl-3-nitrobenzonitrile (16.58 g, 102.3 mmol) in 55 mL of N,N-dimethylformamide (DMF) was added N,N-dimethylacetamide (15.24 g, 128.1 mmol). The reaction mixture turned dark red and was subsequently stirred at 110 °C for 3 hours. After completion of the reaction, the solvent was removed under reduced pressure and the residue was dissolved in a mixture of 300 mL of ethanol and 300 mL of acetic acid. The reaction mixture was heated to 60 °C and iron powder (33 g, 594 mmol) was added in batches. The reaction mixture was refluxed for 2 h. After the reaction was completed, it was filtered through a Hyflo pad. Ether was added to the filtrate and the acidic layer was extracted with ether (1×). The ether layers were combined and concentrated in vacuum. The residue was purified by silica gel column chromatography using dichloromethane as eluent to give 7.02 g (48% yield) of 6-cyanoindaha solid.

References

[1] Patent: US2006/122189, 2006, A1. Location in patent: Page/Page column 20

6-Cyanoindole(15861-36-6)Related Product Information

• Methylene dithiocyanate
• Indole-3-butyric acid
• Indole
• 2-Methylindole
• Indole-3-acetic acid
• Indometacin
• Indole-6-carboxylic acid
• 6-Hydroxyindole
• 3-HYDROXY-1-PHENYL-6-PYRIDAZONE
• 6-cyanopyridine-3-boronic acid
• 6-CHLOROINDOLE-3-ACETONITRILE
• 6-chloropyrazine-2-carbonitrile
• 6-CHLORO-2,3-DIHYDRO-1H-INDOLE
• 6-Cyanopyridine-2-carboxylic acid
• 6-Chloroindole
• 2,3-DIHYDRO-1H-INDOLE-6-CARBONITRILE HYDROCHLORIDE
• 6-Hydroxyindolin-2-one
• Indole-3-carboxaldehyde