3482-14-2

Basic information

• Product Name: 8-Isoquinolinol
• Synonyms: 8-Hydroxyisoquinoline;Isoquinolin-8-ol;8-Hydroxyisoquinoline 96%;8-Isoquinolinol(6CI,7CI,8CI,9CI);2H-isoquinolin-8-one;8-Isoquinolinol;Isoquinolin-8-ol, 8-Hydroxy-2-azanaphthalene;8-Hydroxyisoquinoline95%
• CAS NO: 3482-14-2
• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.16
• EINECS: -0
• Product Categories: ISOQUINOLINE;blocks;Heterocycles;Quinolines;Heterocyclic Series;Quinoline&Isoquinoline;Building Blocks
• Mol File: 3482-14-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 213 °C
• Boiling Point: 332.074 °C at 760 mmHg
• Flash Point: 154.633 °C
• Appearance: /
• Density: 1.26 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.691
• Storage Temp.: 2-8°C
• PKA: 8.40±0.10(Predicted)
• CAS DataBase Reference: 8-Isoquinolinol(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Isoquinolinol(3482-14-2)
• EPA Substance Registry System: 8-Isoquinolinol(3482-14-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• Hazardous Substances Data: 3482-14-2(Hazardous Substances Data)

Usage

General Description

8-Isoquinolinol, also known as 8-hydroxyisoquinoline, is a chemical compound that belongs to the isoquinoline family. It is a heterocyclic compound with a core structure consisting of a benzene ring fused to a pyridine ring. 8-Isoquinolinol has been found to exhibit a variety of biological activities, including anti-inflammatory, antiviral, and antimicrobial properties. It has also been researched for its potential as a chelating agent for metal ions and as a building block for the synthesis of pharmaceutical compounds. 8-Isoquinolinol is a versatile compound with several potential applications in the fields of chemistry, biology, and medicine.

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

Synthetic route

8-methoxyisoquinoline (1723-70-2) → isoquinolin-8-ol (3482-14-2)

Conditions	Yield
Stage #1: 8-methoxyisoquinoline With boron tribromide In dichloromethane at 0 - 20℃; for 2.5h; Heating / reflux; Stage #2: With methanol at -78 - 20℃; for 0.5h; Heating / reflux;	98%
With boron tribromide In dichloromethane for 1h; demethylation; Heating;	83%

8-chloroisoquinoline (34784-07-1) → isoquinolin-8-ol (3482-14-2)

Conditions	Yield
With copper acetylacetonate; lithium hydroxide monohydrate; 1,3-bis(4-hydroxy-2,6-dimethylphenyl)urea In water; dimethyl sulfoxide at 130℃; for 24h; Inert atmosphere;	72%

isoquinoline (119-65-3) → isoquinolin-8-ol (3482-14-2) + cis-7,8-Dihydroisoquinolin-7,8-diol + 5-hydroxyisoquinoline (2439-04-5)

Conditions	Yield
biotransformation by Pseudomonas putida UV4;	A 5 mg B 43 mg C 41 mg

isoquinoline sulfate → isoquinolin-8-ol (3482-14-2)

Conditions	Yield
With sulfuric acid; sulfur trioxide at 300℃; Erhitzen des Reaktionsprodukts mit Natriumhydroxid unter Zusatz von Wasser auf 210grad;

ortho-anisaldehyde (135-02-4) → isoquinolin-8-ol (3482-14-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: benzene / 5 h / Heating 1.2: ClCO2Et; (MeO)3P / 13 / 72 h / 20 °C 1.3: TiCl4 / 15 / 1 h / Heating 2.1: boron tribromide / dichloromethane / 1 h / Heating View Scheme

2C9H6NO(1-)*Cu(2+)*5H2O → isoquinolin-8-ol (3482-14-2)

Conditions	Yield
With sodiumsulfide nonahydrate In ethanol at 40℃; for 20h;

isoquinolin-8-ol (3482-14-2) → C9H5Br2NO

Conditions	Yield
With bromine; sodium hydrogencarbonate In methanol at 20℃; for 0.0833333h;	96%

isoquinolin-8-ol (3482-14-2) → 1,2,3,4-tetrahydro-8-hydroxyisoquinoline acetate (827309-88-6)

Conditions	Yield
With hydrogen; acetic acid; platinum(IV) oxide In ethanol under 3000.3 Torr; for 18h;	92%

isoquinolin-8-ol (3482-14-2) + benzyl bromide (100-39-0) → 8-(benzyloxy)isoquinoline

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 20℃;	90%

isoquinolin-8-ol (3482-14-2) + carbonic acid 1,1-dimethylethyl 1-phenyl-2-propenyl ester (444575-79-5) → C19H17NO

Conditions	Yield
With (S)-(+)-N-(3,5-dioxa-4-phosphacyclohepta-[2,1-a;3,4-a′]dinaphthalen-4-yl)dibenz[b,f]azepine; bis(1,5-cyclooctadiene)diiridium(I) dichloride In methanol at 25℃; for 0.1h; Inert atmosphere; enantioselective reaction;	87%

isoquinolin-8-ol (3482-14-2) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → 8-isoquinolinyl 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranoside

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In chloroform at 60℃;	86%

isoquinolin-8-ol (3482-14-2) + carbonic acid 1,1-dimethylethyl 1-phenyl-2-propenyl ester (444575-79-5) → C18H15NO

Conditions	Yield
With (S)-(+)-N-(3,5-dioxa-4-phosphacyclohepta-[2,1-a;3,4-a′]dinaphthalen-4-yl)dibenz[b,f]azepine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 3,5-dichlorobenzoic acid In methanol at 25℃; for 10h; Inert atmosphere; enantioselective reaction;	78%

isoquinolin-8-ol (3482-14-2) + carbonic acid 1,1-dimethylethyl 1-phenyl-2-propenyl ester (444575-79-5) → C18H15NO

Conditions	Yield
With (S)-(+)-N-(3,5-dioxa-4-phosphacyclohepta-[2,1-a;3,4-a′]dinaphthalen-4-yl)dibenz[b,f]azepine; bis(1,5-cyclooctadiene)diiridium(I) dichloride In methanol at 25℃; for 0.1h; Inert atmosphere; enantioselective reaction;	74%

isoquinolin-8-ol (3482-14-2) + acetic acid (64-19-7) → 1,2,3,4-tetrahydro-8-hydroxyisoquinoline acetate (827309-88-6)

Conditions	Yield
With platinum(IV) oxide; hydrogen at 65℃; for 48h;	72%

isoquinolin-8-ol (3482-14-2) → 1,2,3,4-tetrahydroisoquinoline-8-ol (32999-37-4)

Conditions	Yield
With sodium tetrahydroborate; acetic acid at 20℃; for 1h; Cooling;	71%

4-chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine (659729-09-6) + isoquinolin-8-ol (3482-14-2) → 8-(6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)isoquinoline

Conditions	Yield
Stage #1: isoquinolin-8-ol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 4-chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine In N,N-dimethyl-formamide Further stages.;	63%

isoquinolin-8-ol (3482-14-2) + propyl bromide (106-94-5) → 8-propoxy-isoquinoline (820238-28-6)

Conditions	Yield
Stage #1: isoquinolin-8-ol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: propyl bromide In N,N-dimethyl-formamide at 20℃; for 1h;	63%
Stage #1: isoquinolin-8-ol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: propyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 1h;	63%

isoquinolin-8-ol (3482-14-2) + 3-acetamido-2,6-dichlorobenzyl methanesulfonate (206884-18-6) → 8-(3-acetamido-2,6-dichlorobenzyloxy)isoquinoline

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide Substitution;	25%

isoquinolin-8-ol (3482-14-2) + (1R,3s,5S)-tert-butyl 3-((1s,4S)-4-hydroxycyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate (1430746-24-9) → (1R,3s,5S)-tert-butyl 3-((1r,4R)-4-(isoquinolin-8-yloxy)cyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate (1430745-59-7)

Conditions	Yield
With di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine In tetrahydrofuran at 20℃; for 19h; Inert atmosphere;	16.2%

isoquinolin-8-ol (3482-14-2) + methyl 2-[3-[4-bromo-2-(trifluoromethyl)phenoxy]phenyl]acetate → methyl 2-[3-[4-(8-isoquinolyloxy)-2-(trifluoromethyl)phenoxy]phenyl]acetate

Conditions	Yield
With copper(l) iodide; dimethylaminoacetic acid; caesium carbonate In 1,4-dioxane at 120℃; for 24h; Inert atmosphere; Sealed tube;	12%

isoquinolin-8-ol (3482-14-2) + diethylaminopropylamine (104-78-9) → N,N-diethyl-N'-[8]isoquinolyl-propanediyldiamine

Conditions	Yield
With sulfur dioxide; water unter Druck;

isoquinolin-8-ol (3482-14-2) → 8-aminoisoquinoline (23687-27-6)

Conditions	Yield
With ammonium hydroxide; sulfur dioxide at 150 - 160℃;

isoquinolin-8-ol (3482-14-2) + 4-fluoro-6-(4-(1-(4-fluorophenyl)ethyl)piperazin-1-yl)pyrimidine (862270-56-2) → 8-(6-(4-(1-(4-fluorophenyl)ethyl)piperazin-1-yl)pyrimidin-4-yloxy)isoquinoline

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 115℃; for 0.5h;

isoquinolin-8-ol (3482-14-2) + cefotaxime + trimethylsilyl iodide (16029-98-4) + N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide (24589-78-4) + N-(trimethylsilyl)trifluoroacetamide (55982-15-5) → syn-7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(8-hydroxyisoquinolinium-2-ylmethyl)-3-cephem-4-carboxylate

Conditions	Yield
In tetrahydrofuran; dichloromethane; acetonitrile

isoquinolin-8-ol (3482-14-2) + 1-[(2R)-4-benzoyl-2-methyl-piperazin-1-yl]-2-bromo-propan-1-one (845654-95-7) → C24H25N3O3 (1190841-31-6)

Conditions	Yield
With caesium carbonate In acetone at 20℃; for 24h;

isoquinolin-8-ol (3482-14-2) → 8-propoxy-isoquinoline 2-oxide hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 1 h / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 20 °C 2.2: 0.08 h / 20 °C View Scheme

isoquinolin-8-ol (3482-14-2) → 1-chloro-8-propoxy-isoquinoline (1231948-58-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 1 h / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 20 °C 2.2: 0.08 h / 20 °C 3.1: trichlorophosphate / 5 h / 90 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 1 h / 0 - 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 20 °C 2.2: 0.08 h / 20 °C 3.1: trichlorophosphate / 5 h / 90 °C View Scheme

isoquinolin-8-ol (3482-14-2) → 1-chloro-8-propoxy-isoquinoline-5-sulfonic acid (1231948-59-6) + 1-chloro-8-propoxy-isoquinoline-7-sulfonic acid (1231948-60-9)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 1 h / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 20 °C 2.2: 0.08 h / 20 °C 3.1: trichlorophosphate / 5 h / 90 °C 4.1: fuming sulphuric acid / water / 0.5 h / 0 °C View Scheme

isoquinolin-8-ol (3482-14-2) → 1-chloro-8-propoxy-isoquinoline-5-sulfonic acid (1231948-59-6)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 1 h / 0 - 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 20 °C 2.2: 0.08 h / 20 °C 3.1: trichlorophosphate / 5 h / 90 °C 4.1: sulfur trioxide; sulfuric acid / 0.5 h / 0 °C View Scheme

Upstream product

• 34784-07-1 8-chloroisoquinoline 
• 135-02-4 ortho-anisaldehyde 
• 1723-70-2 8-methoxyisoquinoline 
• 119-65-3 isoquinoline 

Downstream Products

• 23687-27-6 8-aminoisoquinoline 
• 140865-97-0 1-(8-hydroxy-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one 
• 32999-37-4 1,2,3,4-tetrahydroisoquinoline-8-ol 
• 1307298-14-1 4-(1-chloro-8-propoxy-isoquinoline-7-sulfonyl)-[1,4]diazepane-1-carboxylic acid benzyl ester 
• 1190841-31-6 C₂₄H₂₅N₃O₃ 

Relevant articles and documents

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Synthetic method of 8-isoquinolinol

The invention discloses a synthetic method of 8-isoquinolinol, and belongs to the field of synthesis method of isoquinoline compounds. The synthetic method comprises following steps: 8-chloroisoquinoline, copper acetylacetonate, lithium hydroxide monohydrate, and ligand 1,3-bis(4-hydroxyl-2,6-dimethyl phenyl)urea are added into a mixed solution of dimethyl sulfoxide and water; under nitrogen protection, an obtained reaction solution is subjected to heating with stirring until reaction is completed, and pH value is adjusted to 5 with HCl after cooling; an obtained mixed liquid is extracted with ethyl acetate, an obtained organic phase is washed with saturated salt solution, is dried with anhydrous sodium sulfate, and then is subjected to spin drying; and an obtained crude product is subjected to column chromatography separation so as to obtain 8-isoquinolinol. According to the synthetic method, 8-chloroisoquinoline is taken as a raw material; synthesis route is simple; the synthetic method is reasonable; the raw materials are easily available; operation and subsequent treatment are convenient; total yield is as high as 72%; amplify production is convenient to realize; and large-scale production of 8-isoquinolinol can be realized.

Studies on anti-Helicobacter pylori agents. Part 1: Benzyloxyisoquinoline derivatives

The synthesis and optimization of the anti-Helicobacter pylori activity of a novel series of benzyloxyisoquinoline derivatives that was discovered by a random screening process, are described. In the in vitro assay, compound 10c containing a 3-acetamido-2,6-dichlorobenzyl substituent was found to have extremely potent activity against H. pylori and no activity against other common bacteria. The anti-H. pylori activity of 10c was superior to that of amoxicillin (AMPC) (1) and clarithromycin (CAM) (2). However, 10c did not show in vivo efficacy in a mouse infection model; a feature attributed to the lack of strong bactericidal activity at short contact times. (C) 1999 Elsevier Science Ltd.