5-Nitroindole Chemical Properties

Melting point:

140-142 °C (lit.)

Boiling point:

288.82°C (rough estimate)

Density 

1.3264 (rough estimate)

refractive index 

1.5770 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Dichloromethane, Ethyl Acetate, Methanol

form 

Crystalline Powder or Needles

pka

15.25±0.30(Predicted)

color 

Yellow

BRN 

383777

InChI

InChI=1S/C8H6N2O2/c11-10(12)7-1-2-8-6(5-7)3-4-9-8/h1-5,9H

InChIKey

OZFPSOBLQZPIAV-UHFFFAOYSA-N

SMILES

N1C2=C(C=C([N+]([O-])=O)C=C2)C=C1

CAS DataBase Reference

6146-52-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-41

Safety Statements 

26-39-45-36/37

WGK Germany 

3

RTECS 

NM1168200

F 

8

Hazard Note 

Irritant

HazardClass 

IRRITANT, IRRITANT-HARMFUL

HS Code 

29339900

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Eye Dam. 1

MSDS

• Language:English Provider:5-Nitroindole
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Nitroindole Usage And Synthesis

Chemical Properties

Yellow-Green Cyrstalline Solid, soluble in ethanol, diethyl ether, propylene glycol, petroleum ether and most non-volatile oils, insoluble in glycerol and mineral oils.

Application

Reactant for preparation of:

• Pharmaceutically active 2-oxo-1-pyrrolidine analogues
• Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
• Protein Kinase Inhibitors and antiproliferative agents
• Positive Allosteric Modulators of Metabotropic Glutamate Receptor 4 (mGlu4)
• Antifungal agents
• Cannabinoid receptor type 1 (CB1) antagonists
• Potential anticancer agents
• Potential antivascular agents
• Selective Anti-leukemic agents
• Anti human immunodeficiency virus subtype 1 (HIV-1) agents

Uses

5-Nitroindole (cas# 6146-52-7) is a reagent involved in the synthesis of a variety of biochemical compounds, including: 2-oxo-1-pyrrolidine analogs, mGlu4 allosteric modulators, protein kinase inhibitors, antiproliferative agents, anti-HIV 1 agents, antifungal agents, anti-leukemic agents, antivascular agents, anticancer agents, and cannabinoid receptor type 1 (CB1) antagonists.

Synthesis

In 500ml round bottom flask add 27.2g2-sodium-1-acetylindole (0.1mo1), add 100ml acetic acid, cool down to 12??C, in 1h dropwise finish 19ml fuming nitric acid, the reaction is complete, carefully poured into 250ml crushed water, add 160gNaOH, slowly raise the temperature to 70°C, keep for 20h, pumping filtration, wash with 2*100 ml ice water washing, drying, obtained 14.6g of golden yellow crystals 5-Nitroindole, yield 90.1%, purity 98.5%.

Purification Methods

Decolourise (charcoal) 5-nitroindole and recrystallise it twice from aqueous EtOH or recrystallise it from octane. It has UV: 265 and 324nm (EtOH). [Beilstein 20 III/IV 3194, 20/7 V 41.]

5-Nitroindole(6146-52-7)Related Product Information

• 2-Methylindole
• Indole-3-acetic acid
• Indometacin
• Indole
• Indole-3-butyric acid
• 2-METHYL-5-NITROINDOLE
• 5-NITROINDOLE-2-CARBOXYLIC ACID
• 2,3-DIMETHYL-5-NITROINDOLE
• 2-METHYL-5-NITROINDOLE-3-CARBOXALDEHYDE,3-FORMYL-2-METHYL-5-NITROINDOLE
• NITROGEN DIOXIDE
• 5-NITROINDOLE-2-CARBOXYLIC ACID ETHYL ESTER
• 1,3,6,8-TETRANITROCARBAZOLE
• 9-Ethyl-3-nitrocarbazole
• 5-NITRO-3-PHENYL-1H-INDOLE-2-CARBOXYLIC ACID
• 6-Nitrooxidole
• 3-(DIMETHYLAMINOMETHYL)-6-NITROINDOLE
• 2,3-DIMETHYL-7-NITROINDOLE
• 1-ACETYL-5-NITROINDOLINE