2439-04-5

Basic information

• Product Name: 5-Hydroxyisoquinoline
• Synonyms: 5-HYDROXYISOQUINOLINE;5-ISOQUINOLINOL;ISOQUINOLIN-5-OL;5-Hydroxyisoquinolne;5-HYDROXYISOQUINOLINE, TECH., 90%;5-Hydroxyisoquinoline,tech.90%;5-Hydroxyisoquinoline 90%;5-Hydroxyisoquinoline90%
• CAS NO: 2439-04-5
• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.16
• EINECS: 219-456-9
• Product Categories: Heterocyclic Series;Quinolines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 2439-04-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 213-215
• Boiling Point: 264.27°C (rough estimate)
• Flash Point: 154.6 °C
• Appearance: Beige/Granular Powder
• Density: 1.1555 (rough estimate)
• Vapor Pressure: 7.74E-05mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 8.53±0.40(Predicted)
• CAS DataBase Reference: 5-Hydroxyisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxyisoquinoline(2439-04-5)
• EPA Substance Registry System: 5-Hydroxyisoquinoline(2439-04-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-21/22
• Safety Statements: 26-37/39-36/37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 2439-04-5(Hazardous Substances Data)

Usage

Description

5-Hydroxyisoquinoline is an organic compound with the chemical formula C9H7NO and is characterized by its beige granular powder appearance. It is a derivative of isoquinoline, which is a heterocyclic compound with a fused benzene and pyridine ring. The presence of the hydroxyl group in the 5-position of the isoquinoline ring gives it unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
5-Hydroxyisoquinoline is used as a reagent for the preparation of PARP inhibitors. These inhibitors are important in the development of drugs for the treatment of various types of cancer. PARP (Poly (ADP-ribose) polymerase) is an enzyme that plays a crucial role in DNA repair, and its inhibition can lead to the accumulation of DNA damage in cancer cells, ultimately leading to cell death. The use of 5-Hydroxyisoquinoline in the synthesis of these inhibitors contributes to the advancement of cancer therapeutics.
Used in Chemical Research:
Due to its unique chemical structure, 5-Hydroxyisoquinoline can also be used in chemical research for the synthesis of various other organic compounds. Its reactivity and the presence of the hydroxyl group make it a versatile building block for the development of new molecules with potential applications in different fields, such as materials science, pharmaceuticals, and agrochemicals.

InChI:InChI=1/C9H7NO/c11-9-3-1-2-7-6-10-5-4-8(7)9/h1-6,11H

Upstream product

• 119-65-3 isoquinoline 
• 57554-78-6 5-Nitroisoquinoline N-Oxide 
• 607-32-9 5-nitroisoquinoline 
• 1532-72-5 isoquinoline N-oxide 
• 139484-25-6 trans-5-acetoxy-6-bromo-5,6,7,8-tetrahydroisoquinoline 
• 139484-24-5 5-acetoxy-5,6,7,8-tetrahydroisoquinoline 
• 139484-27-8 8-bromo-5,6-epoxy-5,6,7,8-tetrahydroisoquinoline 
• 97112-03-3 5-hydroxy-5,6,7,8-tetrahydroisoquinoline 
• 139484-26-7 5,6-epoxy-5,6,7,8-tetrahydroisoquinoline 
• 50388-20-0 5,6,7,8-tetrahydroisoquinoline N-oxide 
• 24334-24-5 7,8-dihydroisoquinoline 
• 36556-06-6 5,6,7,8-tetrahydroisoquinoline 
• 7664-93-9 sulfuric acid 
• 143247-61-4 (3-hydroxy-benzylidenamino)-acetaldehyde diethylacetal 

Downstream Products

• 130292-81-8 methyl 5-isoquinolyloxyacetate 
• 216064-48-1 2-tert-butyloxycarbonyl-5-hydroxy-1,2,3,4-tetrahydroisoquinoline 
• 1248764-87-5 N-(2-chloro-4-fluorophenyl)-N-(2-cyano-4-fluorophenyl)-2-(5-isoquinolinyloxy)acetamide 
• 1248764-54-6 N-(2-chloro-4-fluorophenyl)-N-(1-ethylpropyl)-2-(5-isoquinolinyloxy)acetamide 
• 1248737-79-2 5-({[3-(2-chloro-4-fluorophenyl)-2-pyridinyl]methyl}oxy)isoquinoline 
• 1248737-93-0 5-({[1-(2-chloro-4-fluorophenyl)-5-fluoro-1H-benzimidazol-2-yl]methyl}oxy)isoquinoline 
• 1248737-99-6 5-[({1-[2-(trifluoromethyl)phenyl]-1H-pyrrol-2-yl}methyl)oxy]isoquinoline 
• 206883-24-1 5-{2-chloro-3-(N,N-diacetylamino)benzyloxy}isoquinoline 
• 206882-50-0 5-(3-acetamido-2,6-dichlorobenzyloxy)isoquinoline 

Relevant articles and documents

Preparation method of tetrahydroisoquinoline derivative

The invention discloses a preparation method of a tetrahydroisoquinoline derivative which is N-Fmoc-1,2,3,4-tetrahydroisoquinoline-5-alcohol. The preparation method comprises the following steps: taking isoquinoline as a starting raw material, loading sulfonic acid groups, hydrolyzing, hydrogenating and carrying out Fmoc protection to obtain a target product. The compound is used as an important medical intermediate.

Investigations of reactions of selected azaarenes with radicals in water. 1. Hydroxyl and sulfate radicals

The oxidative degradation of binuclear azaarenes is studied in a number of environmentally relevant radical reactions. The comparison between oxidation mechanisms of hydroxyl and sulfate radicals, as well as between dark and photoreactions, is done. Most of the products formed are identified. With the change from dark to photoreactions of quinoline and isoquinoline, a shift of the oxidation center from the benzene to the pyridine rings is observed. The reaction behavior of the benzodiazines can be derived from the reaction patterns of quinoline and isoquinoline. The rate constants of second order are determined for the reactions of the azaarenes with carbonate radicals. The rate constants and the differences in the products formed conformably prove the importance of the inclusion of excited states in the reaction mechanism. The application of the frontier orbital concept allows an easy interpretation. Electron transfer reactions resulting in radical oxygen species are shown to be product determining in direct photolysis, too.

Structure and Stereochemistry of cis-Dihydro Diol and Phenol Metabolites of Bicyclic Azaarenes from Pseudomonas putida UV4

Biotransformation of quinoline, isoquinoline, quinoxaline and quinazoline using growing cultures of Pseudomonas putida UV4 yielded cis-dihydro diols from the oxidation of the carbocyclic aromatic ring.Aromatic hydroxylation was observed in both carbocyclic and heterocyclic rings.Ring cleavage of the quinoline skeleton to yield anthranilic acid, and cis-diol formation (with alkene bond reduction) to yield cis-5,6,7,8-tetrahydroquinazoline-5,6-diol from quinazoline were observed.The cis-dihydro diol metabolites of quinoline (5,6- and 7,8-) and quinoxaline (5,6-) were found to be optically pure, while metabolism of isoquinoline gave on e homochiral (5,6-) and one racemic 7,8-) cis-dihydro diol product.The absolute configuration of the cis-dihydro diol metabolites have been determined using 1H NMR analyses, stereochemical correlations and X-ray crystallography methods.