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

Chemical Properties

Yellow-Green Cyrstalline Solid

Uses

Different sources of media describe the Uses of 6146-52-7 differently. You can refer to the following data:
1. Reactant for preparation of:? ;Pharmaceutically active 2-oxo-1-pyrrolidine analogues1? ;Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators2? ;Protein Kinase Inhibitors and antiproliferative agents3? ;Positive Allosteric Modulators of Metabotropic Glutamate Receptor 4 (mGlu4)4? ;Antifungal agents5? ;Cannabinoid receptor type 1 (CB1) antagonists6? ;Potential anticancer agents7? ;Potential antivascular agents8? ;Selective Anti-leukemic agents9? ;Anti human immunodeficiency virus subtype 1 (
2. 5-Nitroindole (cas# 6146-52-7) is a compound useful in organic synthesis.
3. Reactant for preparation of:Pharmaceutically active 2-oxo-1-pyrrolidine analoguesTryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulatorsProtein Kinase Inhibitors and antiproliferative agentsPositive Allosteric Modulators of Metabotropic Glutamate Receptor 4 (mGlu4)Antifungal agentsCannabinoid receptor type 1 (CB1) antagonistsPotential anticancer agentsPotential antivascular agentsSelective Anti-leukemic agentsAnti human immunodeficiency virus subtype 1 (HIV-1) agents

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

• 32692-19-6 5-nitro-2,3-dihydro-1H-indole 
• 88-12-0 1-ethenyl-2-pyrrolidinone 
• 13296-94-1 2-bromo-4-nitroaniline 
• 5192-03-0 5-amino-1H-indole 
• 7596-29-4 acetaldehyde p-nitrophenylhydrazone 
• 32685-24-8 N-[4-(methylphenyl)sulfonyl]-5-nitro-1H-indole 
• 33632-27-8 1-(5-nitro-2,3-dihydroindol-1-yl)ethanone 
• 17422-32-1 5-chloro-1H-indole 
• 1401453-62-0 ethyl 5-nitro-1H-indole-1-carboxylate 
• 621-23-8 1,2,3-trimethoxybenzene 
• 166104-19-4 5-nitroindole-1-carboxylic acid tert-butyl ester 
• 7732-18-5 water 
• 110-16-7 maleic acid 
• 98-95-3 nitrobenzene 

Downstream Products

• 5192-03-0 5-amino-1H-indole 
• 616-79-5 2-amino-5-nitro-benzoic acid 
• 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 

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.