19727-83-4

Basic information

• Product Name: 6-Nitroindoline
• Synonyms: 2,3-DIHYDRO-6-NITRO-(1H)-INDOLE;6-NITROINDOLINE;6-NITRO-2,3-DIHYDROINDOLE;6-NITRO-2,3-DIHYDRO-1H-INDOLE;6-NITRO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE;6-nitro-indolin;6-Nitroindzole;6-NITROINDOLINE, 98+%
• CAS NO: 19727-83-4
• Molecular Formula: C₈H₈N₂O₂
• Molecular Weight: 164.16
• EINECS: 243-257-6
• Product Categories: Indoles and derivatives;Building Blocks;Heterocyclic Building Blocks;Indoles;Building Blocks;C7 to C9;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 19727-83-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 67-69 °C(lit.)
• Boiling Point: 291.62°C (rough estimate)
• Flash Point: 139.3 °C
• Appearance: Orange or red/Crystalline Powder or Crystals
• Density: 1.2739 (rough estimate)
• Vapor Pressure: 0.000762mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 3.39±0.20(Predicted)
• BRN: 156434
• CAS DataBase Reference: 6-Nitroindoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Nitroindoline(19727-83-4)
• EPA Substance Registry System: 6-Nitroindoline(19727-83-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: NM1950000
• Hazardous Substances Data: 19727-83-4(Hazardous Substances Data)

Usage

Chemical Properties

orange crystalline powder or red crystals

Uses

Different sources of media describe the Uses of 19727-83-4 differently. You can refer to the following data:
1. ? ;Reactant for preparation of 2-[(2,3-Dihydro-1H-indol-1-yl)methyl]melatonin analogs as novel MT2-selective melatonin receptor antagonists1? ;Reactant for synthesis of isoindigo and azaisoindigo glycosides as anticancer agents2? ;Reactant for preparation of arylfurancarboxamides with Nav1.8 voltage-gated Na channel blocking/analgesic activities3? ;Reactant for preparation of bicyclic benzamides as 5-HT1 receptor agonists4? ;Reactant for preparation of antiarrhythmic benzopyrans5? ;Reactant for preparation of 5-HT2C/2B receptor antagonists6
2. Reactant for preparation of 2-[(2,3-Dihydro-1H-indol-1-yl)methyl]melatonin analogs as novel MT2-selective melatonin receptor antagonistsReactant for synthesis of isoindigo and azaisoindigo glycosides as anticancer agentsReactant for preparation of arylfurancarboxamides with Nav1.8 voltage-gated Na channel blocking/analgesic activitiesReactant for preparation of bicyclic benzamides as 5-HT1 receptor agonistsReactant for preparation of antiarrhythmic benzopyransReactant for preparation of 5-HT2C/2B receptor antagonists

InChI:InChI=1/C8H8N2O2/c11-10(12)7-2-1-6-3-4-9-8(6)5-7/h1-2,5,9H,3-4H2

Upstream product

• 496-15-1 1-indoline 
• 4769-96-4 6-nitroindole 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 

Downstream Products

• 19232-51-0 1-benzoyl-6-nitro-indoline 
• 15918-79-3 indolin-6-amine 
• 4769-96-4 6-nitroindole 
• 22949-08-2 1-acetyl-6-nitro-2,3-dihydroindole 
• 79063-65-3 C₂₉H₂₆N₂O₇ 
• 79063-63-1 C₂₉H₂₆N₂O₇ 
• 127973-91-5 methyl 3-methoxy-4-<(6-nitro-2,3-dihydroindol-1-yl)methyl>benzoate 
• 1025939-10-9 {(E)-(S)-4-(6-Nitro-2,3-dihydro-indol-1-yl)-4-oxo-1-[2-(trityl-carbamoyl)-ethyl]-but-2-enyl}-carbamic acid tert-butyl ester 
• 5318-27-4 6-amino-1H-indole 

Relevant articles and documents

Discovery of N-indanyl benzamides as potent RORγt inverse agonists

The retinoic acid receptor-related orphan receptor-gamma-t (RORγt) is a promising therapeutic target for treatment of Th17 cell-mediated autoimmune diseases. Based on a scaffold hopping/conformational restriction strategy, a series of N-indanyl benzamides as novel RORγt inverse agonists was discovered. Exploration of structure-activity relationship on the piperazine ring, benzoyl moiety and cyclopentyl moiety of N-indanyl benzamides 2a and 2d led to identification of potent RORγt inverse agonists. Compound 5c with (S)-enantiomer was found having an IC50 of 153.7 nM in Fluorescence Resonance Energy Transfer (FRET) assay, and an IC50 of 47.1 nM in mouse Th17 cell differentiation assay, which represents a promising starting point for developing potent small molecule RORγt inverse agonists. Binding modes of the two enantiomers 5c and 5d in RORγt ligand binding domain were also discussed.

The Relation Between Position and Chemical Composition of Bis-Indole Substituents Determines Their Interactions with G-Quadruplex DNA

G-quadruplex (G4) DNA structures are linked to fundamental biological processes and human diseases, which has triggered the development of compounds that affect these DNA structures. However, more knowledge is needed about how small molecules interact with G4 DNA structures. This study describes the development of a new class of bis-indoles (3,3-diindolyl-methyl derivatives) and detailed studies of how they interact with G4 DNA using orthogonal assays, biophysical techniques, and computational studies. This revealed compounds that strongly bind and stabilize G4 DNA structures, and detailed binding interactions which for example, show that charge variance can play a key role in G4 DNA binding. Furthermore, the structure–activity relationships generated opened the possibilities to replace or introduce new substituents on the core structure, which is of key importance to optimize compound properties or introduce probes to further expand the possibilities of these compounds as tailored research tools to study G4 biology.

Nucleophilic substitution reaction in indole chemistry: 1-methoxy-6-nitroindole-3-carbaldehyde as a versatile building block for 2,3,6-trisubstituted indoles

1-Methoxy-6-nitroindole-3-carbaldehyde is proved to be a versatile electrophile and reacts regioselectively at the 2-position with various types of nucleophiles providing 2,3,6-trisubstituted indole derivatives. The reaction is applicable for the preparation of a novel pyrimido[1,2-a]indole derivative.