6146-52-7

Basic information

• Product Name: 5-Nitroindole
• Synonyms: 5-NITROINDOLE;5-NITRO-1H-INDOLE;5-nitro-indol;Nitroindole;5-Nitroindole,99%;5-Nitroindole,98+%;NSC 520594;5-Nitroindolyl radical
• CAS NO: 6146-52-7
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.15
• EINECS: 228-153-0
• Product Categories: blocks;IndolesOxindoles;NitroCompounds;Indole/indoline/oxindole;indole derivative;Indole and Indoline;Indoles and derivatives;IndoleDerivative;Pyrroles & Indoles;Indole;Indoles;Indole Derivatives;Functional Materials;Organic Nonlinear Optical Materials;Simple Indoles;Pyrroles & Indoles;IndolesPhotonic and Optical Materials;Building Blocks;Heterocyclic Building Blocks;NLO Chromophores and Intermediates;Non-Linear Optical (NLO) Materials;C7 to C9;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Materials Science;NLO Chromophores and Intermediates;Non-Linear Optical (NLO) Materials;Organic and Printed Electronics;Photonic and Optical Materials;Heterocycle-Indole series
• Mol File: 6146-52-7.mol
• Article Data: 40

Chemical Properties

• Melting Point: 140-142 °C(lit.)
• Boiling Point: 288.82°C (rough estimate)
• Flash Point: 173.1 °C
• Appearance: Yellow/Crystalline Powder or Needles
• Density: 1.3264 (rough estimate)
• Vapor Pressure: 3.98E-05mmHg at 25°C
• Refractive Index: 1.5770 (estimate)
• Storage Temp.: -20°C
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• PKA: 15.25±0.30(Predicted)
• BRN: 383777
• CAS DataBase Reference: 5-Nitroindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Nitroindole(6146-52-7)
• EPA Substance Registry System: 5-Nitroindole(6146-52-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-41
• Safety Statements: 26-39-45-36/37
• WGK Germany: 3
• RTECS: NM1168200
• F: 8
• HazardClass: IRRITANT, IRRITANT-HARMFUL
• Hazardous Substances Data: 6146-52-7(Hazardous Substances Data)

Usage

Description

5-Nitroindole, with the CAS number 6146-52-7, is a yellow-green crystalline solid that serves as a versatile compound in organic synthesis and holds significant potential in various pharmaceutical applications due to its unique chemical properties.

Uses

1. Used in Pharmaceutical Synthesis:
5-Nitroindole is used as a reactant for the preparation of pharmaceutically active compounds, including:
a. 2-oxo-1-pyrrolidine analogues
b. Tryptophan dioxygenase inhibitors, such as pyridyl-ethenyl-indoles, which have potential as anticancer immunomodulators
c. Protein Kinase Inhibitors and antiproliferative agents
d. Positive Allosteric Modulators of Metabotropic Glutamate Receptor 4 (mGlu4)
e. Antifungal agents
f. Cannabinoid receptor type 1 (CB1) antagonists
g. Potential anticancer agents
h. Potential antivascular agents
i. Selective Anti-leukemic agents
j. Anti human immunodeficiency virus subtype 1 (HIV-1) agents
These applications span across different industries, such as pharmaceuticals, biotechnology, and medical research, where 5-Nitroindole plays a crucial role in the development of novel therapeutic agents and drug candidates.

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.]

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

Upstream product

• 5192-03-0 5-amino-1H-indole 
• 88-12-0 1-ethenyl-2-pyrrolidinone 
• 13296-94-1 2-bromo-4-nitroaniline 
• 16730-20-4 5-nitro-1H-indole-2-carboxylic acid 
• 32692-19-6 5-nitro-2,3-dihydro-1H-indole 
• 1401453-62-0 ethyl 5-nitro-1H-indole-1-carboxylate 
• 10075-50-0 5-bromo-1H-indole 
• 127-17-3 2-oxo-propionic acid 
• 100-16-3 4-nitrophenylhydrazone 
• 6037-73-6 1-benzyl-2,3-dihydro-1H-indole 
• 496-15-1 1-indoline 
• 73647-04-8 ethyl 2-[2-(4-nitrophenyl)hydrazinylidene]propanoate 
• 16732-57-3 5-nitro-indole-2-carboxylic acid ethyl ester 
• 6293-83-0 2-iodo-4-nitrophenylamine 

Downstream Products

• 72496-82-3 5-Nitro-3-(4-nitro-phenylsulfanyl)-1H-indole 
• 6953-35-1 2-(5-nitro-1H-indol-3-yl)-2-oxoacetyl chloride 
• 138900-17-1 1-(4-fluorophenyl)-5-nitro-1H-indole 
• 107786-36-7 4-[5-nitro-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester 
• 72496-83-4 3-(2,4-Dinitro-phenylsulfanyl)-5-nitro-1H-indole 
• 75392-23-3 5-nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride 
• 79063-62-0 4-Nitro-benzoic acid (3aR,4R,6R,6aS)-2,2-dimethyl-6-(5-nitro-1H-indol-3-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 79063-61-9 4-Nitro-benzoic acid (3aR,4R,6S,6aS)-2,2-dimethyl-6-(5-nitro-1H-indol-3-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 72496-81-2 5-Nitro-3-(2-nitro-phenylsulfanyl)-1H-indole 
• 1147-97-3 5-nitrogramine 
• 6625-96-3 5-nitro-1H-indole-3-carbaldehyde 
• 6958-37-8 5-nitro-1H-indole-3-carboxylic acid 
• 124400-51-7 5-nitro-1-(phenylsulfonyl)-1H-indole 
• 83783-31-7 1-(4-cyanobenzyl)-5-nitroindole 

Relevant articles and documents

Deprotonation of 5-Nitroindole in Micellized Cetyltrimethylammonium Bromide and Hydroxide

The fraction, f, of deprotonation of 5-nitroindole (BH) in cetyltrimethylammonium bromide (CTABr) and NaOH goes through maxima with .In CTAOH micelles f increases smoothly with , even when the indicator is fully micellar bound, and is increased by added NaOH.These variations of f follow the concentrations of BH and OH- in the cationic micelles and the basicity constant in the micellar pseudophase is smaller than in water by a factor of ca. 5.

Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes

An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.

Visible-Light-Promoted Efficient Aerobic Dehydrogenation of N-Heterocycles by a Tiny Organic Semiconductor Under Ambient Conditions

An efficient reusable catalytic system has been developed based on perylene diimide (PDI) organic semiconductor for the aerobic dehydrogenation of N-heterocycles with visible light. This practical catalytic system without any additives proceeds under ambient conditions. The minute aggregates of PDI molecules on the surface of SiO2 nanospheres form tiny organic semiconductors, resulting in high-efficiency photo-oxidative activity. Notably, the robustness of this method is demonstrated by the synthesis of a wide range of N-heteroarenes, gram-scale experiments as well as reusability tests.