3-Cyanoindole Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

3-Cyanoindole Chemical Properties,Usage,Production

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.

Synthesis

A 3-cyanoindole compound synthesis method includes: firstly, taking indole compound, benzyl cyanide and CuI according to the molar ratio of 1:1-2:1-2, placing the indole compound, the benzyl cyanide and the CuI in a reaction vessel, and adding solvent into the reaction vessel until the indole compound and the benzyl cyanide are completely dissolved; then, placing the reaction vessel in oil bath at the temperature of 100-130 DEG C with stirring for reaction for 30-34h, cooling to the room temperature, adding water as same as the solvent in volume, and extracting for 2-4 times by the aid of dichloromethane; and finally, separating using silica gel column chromatography prior to reduced pressure distillation so that the product, namely, the 3-cyanoindole compound is obtained.