5-Cyanoindole Chemical Properties

Melting point:

106-108 °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,Inert atmosphere,Room temperature

solubility 

Chloroform, Hexane, Methanol

pka

15.62±0.30(Predicted)

form 

Crystalline Powder

color 

White to slightly yellow

Water Solubility 

Soluble in chloroform, hexane and methanol. Insoluble in water.

Sensitive 

Air & Light Sensitive

BRN 

116738

InChI

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

InChIKey

YHYLDEVWYOFIJK-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

15861-24-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-22

RIDADR 

3276

WGK Germany 

3

RTECS 

NL5993120

F 

8-10

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29339990

MSDS

• Language:English Provider:1H-Indole-5-carbonitrile
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Cyanoindole Usage And Synthesis

Chemical Properties

Off-White Crystalline Powder

Uses

• ;Reactant for parallel synthesis of dihydroisoquinolines via silver and L-proline co-catalyzed three-component coupling reaction1• ;Reactant for chemoselective and regioselective preparation of benzoyl indoles2• ;Reactant for preparation of novel PPARα/γ dual agonists for potential treatment of metabolic syndrome and IDDM3• ;Reactant for preparation of 4,5-dihydrocyclopenta[c]quinolines by palladium-catalyzed ring-expansion reaction alkynes, using O2 as the oxidant4• ;Reactant for preparation of vinylindoles by hydroarylation of alkynes using indium bromi

Uses

Inhibitor of enzyme.

Uses

Reactant used for parallel synthesis of dihydroisoquinolines via silver and L-proline co-catalyzed three-component coupling reaction, preparation of novel PPARα/γ dual agonists for potential treatment of metabolic syndrome and IDDM, chemo selective and regioselective preparation of benzoyl indoles, 4,5-dihydrocyclopenta[c]quinolines by palladium-catalyzed ring-expansion reaction alkynes, using O2 as the oxidant and vinylindoles by hydroarylation of alkynes using indium bromide catalyst.

Purification Methods

Dissolve the nitrile in 95% EtOH, boil it in the presence of charcoal, filter, evaporate to a small volume and add enough H2O to cause crystallisation and cool. Recrystallise it directly from aqueous EtOH and dry it in a vacuum. UV has at max 276 nm (log 3.6) in MeOH. [Lindwall & Mantell J Org Chem 18 345 1953, 20 1458 1955, Thesing at al. Chem Ber 95 2205 1962, NMR: Lallemend & Bernath Bull Soc Chim Fr 4091 1970, Beilstein 22/3 V 45.]

5-Cyanoindole(15861-24-2)Related Product Information

• Indole
• 6-Cyanoindole
• Indole-3-butyric acid
• Indole-3-acetic acid
• 2-Methylindole
• Indometacin
• Methylene dithiocyanate
• 5-CYANO-2,3-DIHYDRO-1H-INDOLE
• 5-CYANOOXINDOLE
• Indoline
• Indole-5-carboxylic acid
• Methyl indole-5-carboxylate
• Indole-4-carboxylic acid
• Methyl 1H-indole-7-carboxylate
• Indole-6-carboxaldehyde
• Methyl indole-2-carboxylate
• Methyl indole-4-carboxylate
• Indole-3-carboxylic acid