156901-58-5

Basic information

• Product Name: 8-NITROISOQUINOLIN-5-AMINE
• Synonyms: 8-NITROISOQUINOLIN-5-AMINE
• CAS NO: 156901-58-5
• Molecular Formula: C9H7N3O2
• Molecular Weight: 189.17078
• Mol File: 156901-58-5.mol

Chemical Properties

• Melting Point: 260-268 °C (decomp)
• Boiling Point: 459.6±35.0 °C(Predicted)
• Appearance: /
• Density: 1.445±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 3.92±0.36(Predicted)
• CAS DataBase Reference: 8-NITROISOQUINOLIN-5-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-NITROISOQUINOLIN-5-AMINE(156901-58-5)
• EPA Substance Registry System: 8-NITROISOQUINOLIN-5-AMINE(156901-58-5)

Safety Data

• Hazardous Substances Data: 156901-58-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
8-NITROISOQUINOLIN-5-AMINE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its role in drug development is crucial, as it contributes to the creation of new medications with potential therapeutic benefits.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 8-NITROISOQUINOLIN-5-AMINE is utilized for research purposes. It aids in understanding the compound's biological activities and its potential as a precursor to other bioactive molecules.
Used in Dye Production:
8-NITROISOQUINOLIN-5-AMINE is used as a component in the production of dyes. Its chemical properties make it suitable for creating a range of colorants used in various industries.
Used in Organic Product Synthesis:
8-NITROISOQUINOLIN-5-AMINE is also used in the synthesis of organic products, where its unique structure and properties contribute to the development of new organic compounds with specific applications.
Used in Industrial Chemical Production:
8-NITROISOQUINOLIN-5-AMINE finds application in the production of various industrial chemicals, where its chemical reactivity and stability are valuable assets in creating a wide array of products.

Upstream product

• 1125-60-6 isoquinolin-5-ylamine 
• 587-04-2 m-Chlorobenzaldehyde 
• 27461-33-2 N-(isoquinolin-5-yl)acetamide 
• 5430-45-5 5-chloro-isoquinoline 
• 14818-60-1 5-trifluoroacetamidoisoquinoline 
• 502611-98-5 5-trifluoroacetamido-8-nitroisoquinoline 
• 58142-95-3 5-chloro-8-nitroisoquinoline 
• 74-89-5 methylamine 

Relevant articles and documents

Synthesis and flow cytometric evaluation of novel 1,2,3,4-tetrahydroisoquinoline conformationally constrained analogues of nitrobenzylmercaptopurine riboside (NBMPR) designed for probing its conformation when bound to the es nucleoside transporter

Novel regioisomers of conformationally constrained analogues of the potent es nucleoside transporter ligand, nitrobenzylmercaptopurine riboside (NBMPR), designed for probing its bound (bioactive) conformation, were synthesized and evaluated as es transporter ligands by flow cytometry. Purine 6-position 5, 6, 7, or 8-nitro-1,2,3,4-tetrahydroisoquinolylpurine ribosides, in which the nitrobenzyl moiety in NBMPR has been locked into the nitro-1,2,3,4-tetrahydroisoquinoline system, were synthesized by reaction of the appropriate nitro-1,2,3,4-tetrahydroisoquinoline with 6-chloropurine riboside. Flow cytometry was performed using 5-(SAENTA)-X8-fluorescein as the competitive ligand. A high degree of variation in the es transporter binding capacity of the target compounds was observed, with the Ki values ranging from 0.45 nM for the most tightly bound compound (4) to 300 nM for the least tightly bound compound (5). The Ki of NBMPR was 0.70 nM, a little higher than that of compound 4. Compound 4 is the isomer that has the nitro group in the best orientation at the es transporter binding site compared to the other three compounds, 2, 3, and 5.

Amination of Some Nitroisoquinolines with Liquid Methylamine/Potassium Permanganate

5-Nitro-, 3-methyl-5-nitro-, 5,7-dinitro-, 5-chloro-8-nitro- and 8-chloro-5-nitroisoquinoline (1a-e) as well as 5-nitroisoquinoline N-oxide (1f) are aminated with a liquid methylamine solution of potassium permanganate (LMA/PP) to the corresponding mono- or mono- and bis(methylamino)-substituted nitro compounds 2 (a-m). 1-Nitroisoquinoline (1g) is aminated with LMA/PP to 1-(methylamino)isoquinoline (2n).Quantum-chemical calculations for some mononitroisoquinolines suggest that, in general, the experimentally observed regioselectivity of the amination is controlled by an interaction of frontal molecular orbitals (FMO) of the reagents. - Key Words: Methylaminations / Calculations, FMO / Isoquinolines / Aminations / Nitro compounds