110568-64-4

Basic information

• Product Name: 6-NITRO-ISOINDOLIN-1-ONE
• Synonyms: 6-NITRO-ISOINDOLIN-1-ONE;6-Nitroisoindoline-1-one;6-Nitro-2,3-dihydro-isoindol-1-one;1H-Isoindol-1-one, 2,3-dihydro-6-nitro-;6-nitro-2,3-dihydro-1H-isoindol-1-one
• CAS NO: 110568-64-4
• Molecular Formula: C₈H₆N₂O₃
• Molecular Weight: 178.15
• Mol File: 110568-64-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: 253 °C (decomp)
• Boiling Point: 487.473 °C at 760 mmHg
• Flash Point: 248.615 °C
• Appearance: /
• Density: 1.45 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.56±0.20(Predicted)
• CAS DataBase Reference: 6-NITRO-ISOINDOLIN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-NITRO-ISOINDOLIN-1-ONE(110568-64-4)
• EPA Substance Registry System: 6-NITRO-ISOINDOLIN-1-ONE(110568-64-4)

Safety Data

• Hazardous Substances Data: 110568-64-4(Hazardous Substances Data)

Usage

Description

6-NITRO-ISOINDOLIN-1-ONE, also known as 6-nitro-3,4-dihydro-2H-1-benzazepin-2-one, is a chemical compound with the molecular formula C8H6N2O3. It is a nitro-substituted isoindolinone derivative characterized by its yellow crystalline appearance. 6-NITRO-ISOINDOLIN-1-ONE is recognized for its diverse applications in the synthesis of pharmaceuticals, agrochemicals, dyes, and pigments, as well as for its biological activities such as anti-inflammatory and anti-tumor properties. Its potential in pharmacological applications and its role as a versatile building block in organic synthesis make 6-NITRO-ISOINDOLIN-1-ONE a valuable compound in the fields of medicinal chemistry and chemical research.

Uses

Used in Pharmaceutical Synthesis:
6-NITRO-ISOINDOLIN-1-ONE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Production:
In the agrochemical industry, 6-NITRO-ISOINDOLIN-1-ONE is used as a precursor in the production of agrochemicals, contributing to the development of effective crop protection agents.
Used in Dye and Pigment Manufacturing:
6-NITRO-ISOINDOLIN-1-ONE is utilized as a building block in the manufacturing of dyes and pigments, where its chemical properties are leveraged to create a range of colorants for various industries.
Used in Medicinal Chemistry Research:
6-NITRO-ISOINDOLIN-1-ONE is employed as a versatile compound in medicinal chemistry research, where its unique structure and properties are explored for the discovery of new therapeutic agents and drug candidates.
Used in Organic Synthesis:
As a valuable building block in organic synthesis, 6-NITRO-ISOINDOLIN-1-ONE is used to construct complex organic molecules, facilitating advancements in the synthesis of novel compounds with potential applications in various fields.

InChI:InChI=1/C8H6N2O3/c11-8-7-3-6(10(12)13)2-1-5(7)4-9-8/h1-3H,4H2,(H,9,11)

Upstream product

• 3006-64-2 2-acetyl-2,3-dihydro-1H-isoindol-1-one 
• 110568-91-7 6-nitro-2-nitroso-isoindolin-1-one 
• 5415-18-9 2,3-Dihydro-2-nitroso-1H-isoindol-1-on 
• 480-91-1 oxisoindole 
• 133446-99-8 2-bromomethyl-4-nitro-benzoic acid methyl ester 
• 77324-87-9 methyl 2-methyl-5-nitrobenzoate 
• 90725-68-1 methyl 2-(bromomethyl)-5-nitrobenzoate 
• 110568-91-7 2,3-Dihydro-6-nitro-2-nitroso-1H-isoindol-1-on 
• 62621-09-4 methyl 2-methyl-4-nitrobenzoate 
• 1975-51-5 2-methyl-4-nitrobenzoic acid 

Downstream Products

• 222036-66-0 5-amino-2,3-dihydro-1H-benzo[c]azol-1-one 
• 675109-46-3 (3-oxo-2,3-dihydro-1H-isoindol-5-yl)carbamic Acid Tert-Butyl Ester 
• 675109-45-2 6-aminoisoindolin-1-one 

Relevant articles and documents

Synthesis, computational, and spectroscopic analysis of tunable highly fluorescent BN-1,2-azaborine derivatives containing the N-BOH moiety

Nine new polycyclic aromatic BN-1,2-azaborine analogues containing the N-BOH moiety were synthesized using a convenient two-step, one-pot procedure. Characterization of the prepared compounds show the luminescence wavelength and the quantum yields of the azaborines were tunable by controlling the power and location of the donor and acceptor substituents on the chromophore. UV-visible spectroscopy and density functional theory (DFT) computations revealed that the addition of electron-donating moieties to the isoindolinone hemisphere raised the energy of the HOMO, resulting in the reduction of the HOMO-LUMO gap. The addition of an electron-accepting moiety to the isoindolinone hemisphere and an electron-donating group to the boronic acid hemisphere decreased the HOMO-LUMO gap considerably, leading to emission properties from partial intramolecular charge transfer (ICT) states. The combined effect of an acceptor on the isoindolinone side and a donor on the boronic acid side (strong acceptor-π-donor) gave the most red-shifted absorption. The polycyclic aromatic BN-1,2-azaborines emitted strong fluorescence in solution and in the solid-state with the largest red-shifted emission at 640 nm and a Stokes shift of Δλ = 218 nm, or Δν = 8070 cm-1.

BIOREVERSABLE PROMOIETIES FOR NITROGEN-CONTAINING AND HYDROXYL-CONTAINING DRUGS

Disclosed are promoieties of the following formula which can be used to form prodrugs of nitrogen-containing or hydroxyl-containing drug or a pharmaceutically active agent: (I) and pharmaceutical compositions comprising the prodrugs.

Construction of a turn-on probe for fast detection of H2S in living cells based on a novel H2S trap group with an electron rich dye

A turn-on probe (ANR) for fast detection of H2S is constructed based on a 2-(azidomethyl)-4-nitrobenzoate moiety as a trap group. This group is very effective for the design of H2S probes especially with electron rich dyes. The potential biological applications of ANR were proved by employing it for fluorescence imaging of H2S in living cells.