63927-23-1

Basic information

• Product Name: 5-Bromo-8-nitroisoquinoline
• Synonyms: 5-BROMO-8-NITROISOQUINOLINE;Isoquinoline, 5-bromo-8-nitro-;5-BroMo-8-nitroisoquinolilne;5-Bromo-8-nitroisoquinoline 90%
• CAS NO: 63927-23-1
• Molecular Formula: C₉H₅BrN₂O₂
• Molecular Weight: 253.05
• EINECS: -0
• Product Categories: Halides;Heterocycles;Halogenated Heterocycles;Heterocyclic Building Blocks;Isoquinolines;IsoquinolinesBuilding Blocks
• Mol File: 63927-23-1.mol
• Article Data: 39

Chemical Properties

• Melting Point: 136-140 °C
• Boiling Point: 386.949 °C at 760 mmHg
• Flash Point: 187.82 °C
• Appearance: yellow solid
• Density: 1.748 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.707
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2?+-.0.36(Predicted)
• CAS DataBase Reference: 5-Bromo-8-nitroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-8-nitroisoquinoline(63927-23-1)
• EPA Substance Registry System: 5-Bromo-8-nitroisoquinoline(63927-23-1)

Safety Data

• Hazard Codes: T
• Statements: 25-37/38-41
• Safety Statements: 26-39-45
• RIDADR: UN 2811
• WGK Germany: 3
• Hazardous Substances Data: 63927-23-1(Hazardous Substances Data)

Usage

General Description

5-Bromo-8-nitroisoquinoline is a chemical compound with the molecular formula C9H5BrN2O2. It is a heterocyclic compound that consists of a seven-membered ring containing nitrogen, and it is characterized by the presence of a bromine and nitro group. 5-Bromo-8-nitroisoquinoline is used in the field of organic synthesis as a building block for the preparation of pharmaceuticals, agrochemicals, and other organic compounds. It is also used as a reagent in the synthesis of new materials and as a key intermediate in the production of fine chemicals. 5-Bromo-8-nitroisoquinoline has potential applications in medicinal chemistry and can be used as a starting material for the preparation of various bioactive molecules.

InChI:InChI=1/C9H5BrN2O2/c10-8-1-2-9(12(13)14)7-5-11-4-3-6(7)8/h1-5H

Upstream product

• 34784-04-8 5-bromoisoquinoline 
• 119-65-3 isoquinoline 
• 1125-60-6 isoquinolin-5-ylamine 

Downstream Products

• 196198-67-1 N-[2-(4-Hydroxy-phenyl)-ethyl]-4-[2-(6-nitro-2,3-dioxo-1,2,3,4,7,10-hexahydro-8H-pyrido[3,4-f]quinoxalin-9-yl)-acetylamino]-butyramide 
• 1092063-62-1 5-(5-fluoro-2-hydroxyphenyl)-3-(hydroxyimino)-8-methyl-6,7,8,9-tetrahydro-1H-pyrrolo[3,2-h]isoquinolin-2(3H)-one 
• 1092063-78-9 5-(5-fluoro-2-methoxyphenyl)-8-methyl-6,7,8,9-tetrahydro-1H-pyrrolo[3,2-h]isoquinoline-2,3-dione 
• 1092063-77-8 N-(5-(5-fluoro-2-methoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-8-yl)-2-(hydroxyimino)acetamide 
• 1092063-76-7 5-(5-fluoro-2-methoxyphenyl)-2-methyl-8-nitro-1,2,3,4-tetrahydroisoquinoline 
• 952598-51-5 5-(5-fluoro-2-methoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-8-amine 
• 938170-27-5 5-(5-fluoro-2-methoxyphenyl)-6,7,8,9-tetrahydro-3-(hydroxyimino)-8-methyl-1H-pyrrolo[3,2-h]isoquinoline-2(3H)-one 
• 1602769-95-8 5-(4-methoxybenzylthio)-8-nitroisoquinoline 
• 1353967-90-4 5-[2-(2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-8-methoxy-isoquinolin-3-ylamine 
• 1353967-59-5 5-[2-(2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-8-methoxy-isoquinolin-1-ylamine 
• 1353970-14-5 2-(2-fluoro-phenyl)-4-(8-methoxy-2-oxy-isoquinolin-5-yl)-[1,8]naphthyridine 
• 1353970-11-2 2-(2-fluoro-phenyl)-4-(8-nitro-2-oxy-isoquinolin-5-yl)-[1,8]naphthyridine 
• 104737-00-0 5-bromo-2-methyl-8-nitro-1,2,3,4-tetrahydroisoquinoline 
• 171619-73-1 5-bromo-2-(1-methylpropyl)-1,2,3,4-tetrahydro-8-nitroisoquinoline 

Relevant articles and documents

Discovery of Benzopyridone-Based Transient Receptor Potential Vanilloid 1 Agonists and Antagonists and the Structural Elucidation of Their Activity Shift

Among a series of benzopyridone-based scaffolds investigated as human transient receptor potential vanilloid 1 (TRPV1) ligands, two isomeric benzopyridone scaffolds demonstrated a consistent and distinctive functional profile in which 2-oxo-1,2-dihydroquinolin-5-yl analogues (e.g., 2) displayed high affinity and potent antagonism, whereas 1-oxo-1,2-dihydroisoquinolin-5-yl analogues (e.g., 3) showed full agonism with high potency. Our computational models provide insight into the agonist-antagonist boundary of the analogues suggesting that the Arg557 residue in the S4-S5 linker might be important for sensing the agonist binding and transmitting signals. These results provide structural insights into the TRPV1 and the protein-ligand interactions at a molecular level.

A 8-nitro -1, 2, 3, 4-isoquinoline method for the preparation of (by machine translation)

This invention has offered a kind of 8-nitro -1, 2, 3, 4-isoquinoline method for preparing, comprising the following steps: a) isoquinoline and bromizing to the bromination reaction in a strong acid solution, to obtain 5-bromo-isoquinoline; b) the nitrate and step a) the obtained 5-bromo-isoquinoline in the nitration reaction carried out in concentrated sulfuric acid, to obtain 8-nitro-5-bromo-isoquinoline; c) under the conditions of the hydrogen gas, the step b) of 8-nitro-5-bromo-isoquinoline in the solvent under the action of the catalyst to the catalytic hydrogenation Debrominative reaction, to obtain 8-nitro-isoquinoline; d) the step c) of the 8-nitro-isoquinoline with sodium borohydride in acetic acid in the reduction reaction, to obtain 8-nitro -1, 2, 3, 4-isoquinoline. Compared with the prior art, the present invention provides the preparation method of the isoquinoline uses the bromine first 5-C positioning, the subsequent nitration reaction only in 8-C to on, and then sequentially through the catalytic hydrogenation of less impurities are Debrominative and the reduction reaction, the obtained 8-nitro -1, 2, 3, 4-isoquinoline high yield. (by machine translation)

Design and synthesis of brain penetrant selective JNK inhibitors with improved pharmacokinetic properties for the prevention of neurodegeneration

The SAR of a series of brain penetrant, trisubstituted thiophene based JNK inhibitors with improved pharmacokinetic properties is described. These compounds were designed based on information derived from metabolite identification studies which led to compounds such as 42 with lower clearance, greater brain exposure and longer half life compared to earlier analogs.