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

• 16730-20-4 5-nitro-1H-indole-2-carboxylic acid 
• 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 
• 120-72-9 indole 
• 108-24-7 acetic anhydride 
• 32685-24-8 N-[4-(methylphenyl)sulfonyl]-5-nitro-1H-indole 
• 125600-42-2 2-amino-5-nitrophenylacetylene 
• 127-17-3 2-oxo-propionic acid 
• 100-16-3 4-nitrophenylhydrazone 
• 124400-51-7 5-nitro-1-(phenylsulfonyl)-1H-indole 
• 10075-50-0 5-bromo-1H-indole 
• 1401453-62-0 ethyl 5-nitro-1H-indole-1-carboxylate 

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.

Exploring the Labile Nature of 2,4,6-Trimethoxyphenyl Moiety in Allylic Systems under Acidic Conditions

An investigation of the unexpected lability of the Csp3–Csp2 bond connecting 2,4,6-trimethoxyphenyl group and an allylic moiety is carried out. We observed that the catalytic presence of either Lewis or Br?nsted acid can render such 2,4,6-trimethoxyphenyl group labile. Several nucleophiles were found to substitute the labile C–C bond in mild reaction conditions resulting in very good yields of the allylated products. Even in the absence of a nucleophile, intramolecular cyclization of the parent substrate under acidic activation caused the labile C–C bond to cleave. A major motivation of this study is to understand the lability of electron-rich aryl group in acidic medium, employing 2,4,6-trimethoxyphenyl moiety as a case study. A plausible mechanism is proposed after carrying out several control reactions as well as UV/Vis and 1H NMR spectroscopic studies. This work provides an insight into the activation of electron-rich arenes as a labile entity in acidic medium while also adding a conceptually novel C–C bond breaking approach to the vast literature of allylation of arenes.

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.