3-Cyanoindole

Synonym(s):3-Indolecarbonitrile;NSC 24935

CAS NO.：5457-28-3
Empirical Formula: C9H6N2
Molecular Weight: 142.16
MDL number: MFCD00022717
EINECS: 212-232-1
SAFETY DATA SHEET (SDS)
Update Date: 2023-04-23 13:52:06

What is 3-Cyanoindole?

Chemical properties

brown-grey to brown crystalline powder

The Uses of 3-Cyanoindole

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

The Uses of 3-Cyanoindole

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

Reactant for:

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

What are the applications of Application

3-Cyanoindole is 3-Cyanoindole is a reactant for preparation of 4-substituted β-lactams, biologically active Indoles, inhibitors of glycogen synthase kinase 3β (GSK-3).

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.

Properties of 3-Cyanoindole

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
CAS DataBase Reference	5457-28-3(CAS DataBase Reference)
NIST Chemistry Reference	3-Indolecarbonitrile(5457-28-3)

Safety information for 3-Cyanoindole

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H312:Acute toxicity,dermal H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H332:Acute toxicity,inhalation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up.