84807-26-1

Basic information

• Product Name: 4-NITRO-2,3-DIHYDRO-1H-INDOLE
• Synonyms: 4-NITRO-2,3-DIHYDRO-1H-INDOLE;4-NITRO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE;4-nitroindoline;1H-INDOLE,2,3-DIHYDRO-4-NITRO;2,3-Dihydro-4-nitro-1H-indole
• CAS NO: 84807-26-1
• Molecular Formula: C₈H₈N₂O₂
• Molecular Weight: 164.16
• Mol File: 84807-26-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 185-186 °C
• Boiling Point: 307.586 °C at 760 mmHg
• Flash Point: 139.823 °C
• Appearance: /
• Density: 1.299 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 3.45±0.20(Predicted)
• CAS DataBase Reference: 4-NITRO-2,3-DIHYDRO-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITRO-2,3-DIHYDRO-1H-INDOLE(84807-26-1)
• EPA Substance Registry System: 4-NITRO-2,3-DIHYDRO-1H-INDOLE(84807-26-1)

Safety Data

• Hazardous Substances Data: 84807-26-1(Hazardous Substances Data)

Usage

General Description

4-Nitro-2,3-dihydro-1H-indole is a chemical compound with the molecular formula C8H8N2O2. It is a nitrogen-containing heterocyclic compound that contains a nitro group. 4-Nitro-2,3-dihydro-1H-indole is a yellow crystalline solid that is insoluble in water but soluble in organic solvents. It is primarily used as a building block in the synthesis of pharmaceuticals and other organic compounds. The presence of the nitro group makes 4-Nitro-2,3-dihydro-1H-indole a valuable intermediate in organic chemistry, as it can undergo various chemical reactions to produce a wide range of different compounds. However, it is important to handle this compound with care, as it is potentially hazardous and may pose health risks if not properly managed.

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Relevant articles and documents

Compound with indoline skeleton, and preparation method and medical application of compound

The invention discloses a compound with an indoline skeleton, and a preparation method and medical application of the compound. The compound containing the indoline skeleton provided by the inventioncan interfere with Keap1-Nrf2 interaction activate Nrf2

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.

Synthesis of 2'-deoxyribofuranosyl indole nucleosides related to the antibiotics SF-2140 and neosidomycin

The 2'-deoxyribofuranose analog of the naturally occurring antibiotics SF-2140 and neosidomycin were prepared by the direct glycosylation of the sodium salts of the appropriate indole derivatives, with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythropentofuranose. Thus, treatment of the sodium salt of 4-methoxy-1H-indol-3-ylacetonitrile with 5 provided the blocked nucleoside, 4-methoxy-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythropentofuranosyl)-1 -indol-3-ylacetonitrile, which was treated with sodium methoxide to yield the SF-2140 analog, 4-methoxy-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indol-3-ylacetoni rile. The neosidomycin analog was prepared by treatment of the sodium salt of 1H-indol-3-ylacetonitrile with 5 to obtain the blocked intermediate 1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythropentofuranosyl)-1H-3-ylacet nitrile followed by sodium methoxide treatment to give 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indol-3-ylacetonitrile and finally conversion of the nitrile function of 7b to provide 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indol-3-ylacetamide. In a similar manner, indole and several other substituted indoles including 1H-indole-4-carbonitrile, 4-nitro-1H-indole, 4-chloro-1H-indole-2-carboxamide and 4-chloro-1H-indole-2-carbonitrile were each glycosylated and deprotected to provide 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole, 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole-4-carbonitrile, 4-nitro-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole, 4-chloro-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole-2-carboxami e and 4-chloro-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole-2-carbonitr le, respectively. The 2'-deoxyadenosine analog in the indole ring system was prepared for the first time by reduction of the nitro group of 11c using palladium on carbon thus providing 4-amino-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole (1,3,7-trideaza-2'-deoxyadenosine).