3-Cyanoindole Chemical Properties

Melting point:

179-182 °C (lit.)

Boiling point:

249.72°C (rough estimate)

Density 

1.1777 (rough estimate)

refractive index 

1.6211 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

14.61±0.30(Predicted)

color 

Orange to Brown

Water Solubility 

Insoluble in water.

Sensitive 

Air & Light Sensitive

BRN 

120888

InChI

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

InChIKey

CHIFTAQVXHNVRW-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

5457-28-3(CAS DataBase Reference)

NIST Chemistry Reference

3-Indolecarbonitrile(5457-28-3)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-37/39-36/37/39

RIDADR 

3439

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Cyanoindole Usage And Synthesis

Chemical Properties

brown-grey to brown crystalline powder

Uses

3-Cyanoindole (cas# 5457-28-3) is a compound useful in organic synthesis.

Uses

Reactant for preparation of:

• Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
• Inhibitors of the C-terminal domain of RNA polymerase II with antitumor activities
• 4-substituted β-lactams
• Biologically active Indoles
• Inhibitors of glycogen synthase kinase 3β (GSK-3)
• HIV-1 integrase inhibitors
• Indole fragments as inosine monophosphate dehydrogenase (IMPDH) inhibitors
• Aziridinomitosene skeleton
• Potential antiviral agents

• Intramolecular oxidative C-H coupling reactions with applications in medium-ring synthesis techniques

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 5, p. 656, 1973
Tetrahedron, 50, p. 6549, 1994 DOI: 10.1016/S0040-4020(01)89685-X
Tetrahedron Letters, 18, p. 4417, 1977 DOI: 10.1016/S0040-4039(01)83524-3

General Description

3-Cyanoindole undergoes regiospecific bromination to afford 6-bromo-3-cyanoindole. 3-Cyanoindole is formed during the flash vacuum thermolysis (FVT) of 3-azidoquinoline.

3-Cyanoindole(5457-28-3)Related Product Information

• p-Tolunitrile
• Indole-3-butyric acid
• 4-Nitrobenzonitrile
• 2-Methylindole
• Indole-3-carboxylic acid
• Indole-3-acetic acid
• 2-Cyanophenol
• Indometacin
• 2-Chloro-3-cyanopyridine
• Benzonitrile
• Indole
• Ethyl indole-3-carboxylate
• Indole-4-carboxaldehyde
• 6-CYANOINDOLE,CYANOINDOLE-6
• 4-CYANOINDOLE
• 1-BOC-5-CYANOINDOLE
• 7-CYANOINDOLE
• Carbonitrile