7651-82-3

Basic information

• Product Name: Isoquinolin-6-ol
• Synonyms: 6-HYDROXYISOQUINOLINE;isoquinolin-6-ol;2H-Isoquinolin-6-one;6-Isoquinolinol;Einecs 231-612-8;Isoquinolin-6-ol, 6-Hydroxy-2-azanaphthalene;6-Hydroxyisoquinoline96%
• CAS NO: 7651-82-3
• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.16
• EINECS: 231-612-8
• Product Categories: blocks;Heterocycles;Quinolines;Heterocyclic Series;Quinoline&Isoquinoline;Building Blocks;Isoquinoline
• Mol File: 7651-82-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 220 °C
• Boiling Point: 332.1 °C at 760 mmHg
• Flash Point: 154.6 °C
• Appearance: white to light yellow crystal powder
• Density: 1.26 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.691
• Storage Temp.: 2-8°C
• PKA: 9.15±0.10(Predicted)
• CAS DataBase Reference: Isoquinolin-6-ol(CAS DataBase Reference)
• NIST Chemistry Reference: Isoquinolin-6-ol(7651-82-3)
• EPA Substance Registry System: Isoquinolin-6-ol(7651-82-3)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 7651-82-3(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

6-Hydroxyisoquinoline is used in proteomics research such as in preparation of isoquinoline derivatives which act as protease inhibitors against trypsin. It was also used as a reagent in the study of a novel series of compounds that act as Wnt signaling pathway inhibitors and obtained by scaffold hybridization strategy from two known porcupine inhibitor classes.

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

Synthetic route

methanol (67-56-1) + C18H15NO → isoquinolin-6-ol (7651-82-3) + (R)-1-phenyl-1-methoxyprop-2-ene (22665-13-0)

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-(+)-(3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-5H-dibenz[b,f]azepine; 3,5-dichlorobenzoic acid at 25℃; for 10h; Inert atmosphere;	A 93% B 99%

6-methoxyisoquinoline (52986-70-6) → isoquinolin-6-ol (7651-82-3)

Conditions	Yield
With aqueous HBr In water	82%
With pyridine hydrochloride at 160℃;	27%
Stage #1: 6-methoxyisoquinoline With pyridine hydrochloride at 160℃; Stage #2: With water; ammonium hydroxide at 20℃; pH=10 - 11;	27%

6-bromo-isoquinoline (34784-05-9) → isoquinolin-6-ol (7651-82-3)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium hydroxide; tert-butyl XPhos In 1,4-dioxane; water at 100℃; for 1.5h;	75%

2C9H6NO(1-)*Cu(2+)*5H2O → isoquinolin-6-ol (7651-82-3)

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

methanol (67-56-1) + C18H14FNO → isoquinolin-6-ol (7651-82-3) + C10H11FO

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-(+)-(3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-5H-dibenz[b,f]azepine; 3,5-dichlorobenzoic acid at 25℃; Inert atmosphere;

methanol (67-56-1) + C18H14FNO → isoquinolin-6-ol (7651-82-3) + C10H11FO

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-(+)-(3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-5H-dibenz[b,f]azepine; 3,5-dichlorobenzoic acid at 25℃; Inert atmosphere;

isoquinolin-6-ol (7651-82-3) → 5-iodoisoquinolin-6-ol (918488-43-4)

Conditions	Yield
Stage #1: isoquinolin-6-ol With trifluorormethanesulfonic acid; [bis(pyridine)iodine]+ tetrafluoroborate In dichloromethane at 0 - 20℃; for 3h; Stage #2: With sodium hydrogencarbonate In water	97%

isoquinolin-6-ol (7651-82-3) + cyclobutanol (2919-23-5) → 6-cyclobutoxyisoquinoline

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 21h; Mitsunobu Displacement; Inert atmosphere;	97%

isoquinolin-6-ol (7651-82-3) + 2-bromo-2-methylpropanamide (7462-74-0) → 2-(isoquinoline-6-yloxy)-2-methylpropanamide

Conditions	Yield
With sodium hydride In 1,4-dioxane; mineral oil at 100℃; for 8h;	95%

isoquinolin-6-ol (7651-82-3) → 5-bromoisoquinoline-6-ol (918488-42-3)

Conditions	Yield
With flavin reductase enzyme from E. Coli; radicicol halogenase from Chaetomium chiversii D456E/T501S mutant; β-nicotinamide adenine dinucleotide reduced; riboflavin adenine dinucleotide; potassium bromide In aq. phosphate buffer; ethanol at 30℃; for 2h; pH=7.4; Enzymatic reaction; regioselective reaction;	92%
Stage #1: isoquinolin-6-ol With bromine In chloroform at 20℃; for 2h; Stage #2: With sodium hydrogencarbonate In water	88%
Stage #1: isoquinolin-6-ol With bromine In chloroform at 20℃; for 2h; Stage #2: With water; sodium hydrogencarbonate pH=8;	88%

isoquinolin-6-ol (7651-82-3) → 5-chloro-6-hydroxyisoquinoline (918488-41-2)

Conditions	Yield
Stage #1: isoquinolin-6-ol With sulfuryl dichloride In diethyl ether; dichloromethane at 20℃; for 5h; Stage #2: With sodium hydrogencarbonate In water	89%
Stage #1: isoquinolin-6-ol With sulfuryl dichloride In dichloromethane at 20℃; for 5h; Stage #2: With water; sodium hydrogencarbonate	89%
With Escherichia coli BL21-CodonPlus (DE3)-RIL/pJZ54 Enzymatic reaction;	11.4 mg
With flavin reductase enzyme from E. Coli; radicicol halogenase from Chaetomium chiversii D456E/T501S mutant; β-nicotinamide adenine dinucleotide reduced; riboflavin adenine dinucleotide; magnesium chloride In aq. phosphate buffer; ethanol at 30℃; for 2h; pH=7.4; Kinetics; Catalytic behavior; Reagent/catalyst; Enzymatic reaction; regioselective reaction;

isoquinolin-6-ol (7651-82-3) + (benzylseleninyl)benzene (13154-11-5) → 5-(phenylselanyl)isoquinolin-6-ol

Conditions	Yield
With trifluoroacetic anhydride In dichloromethane at 20℃; for 1h; Inert atmosphere; Glovebox; Sealed tube;	84%

isoquinolin-6-ol (7651-82-3) + (S)-(-)-tert-butyl 1-phenylprop-2-en-1-yl carbonate (444575-89-7) → 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 0.1h; Inert atmosphere; enantioselective reaction;	82%

isoquinolin-6-ol (7651-82-3) + isopropyl alcohol (67-63-0) → 6-isopropoxyisoquinoline

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h; Mitsunobu Displacement; Inert atmosphere;	80%

isoquinolin-6-ol (7651-82-3) + (+/-)-1-(4'-fluorophenyl)prop-2-en-1-yl tert-butyl carbonate (1073277-35-6) → C18H14FNO

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 0.166667h; Inert atmosphere; enantioselective reaction;	80%

isoquinolin-6-ol (7651-82-3) + 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;	80%

isoquinolin-6-ol (7651-82-3) + tert-butyl (1-(4-chlorophenyl)allyl) carbonate (1314581-30-0) → C18H14ClNO

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-6-ol (7651-82-3) + 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-6-ol (7651-82-3) + (+/-)-1-(4'-fluorophenyl)prop-2-en-1-yl tert-butyl carbonate (1073277-35-6) → C18H14FNO

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;	77%

isoquinolin-6-ol (7651-82-3) + C19H27NO5 → C23H24N2O3

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; dibenzenesulfonamide In methanol at 25℃; for 11h; Inert atmosphere; enantioselective reaction;	77%

isoquinolin-6-ol (7651-82-3) + 2-bromo-2-methylpropionic acid methyl ester (23426-63-3) → methyl 2-(isoquinolin-6-yloxy)-2-methylpropanoate (945860-77-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 16h;	74%

isoquinolin-6-ol (7651-82-3) + chloroacetonitrile (107-14-2) → 2-(cyanomethyl)-6-hydroxyisoquinolinium chloride (1383730-50-4)

Conditions	Yield
In N,N-dimethyl-formamide for 4h; Reflux;	74%

isoquinolin-6-ol (7651-82-3) + (R)-(+)-tert-butyl 1-phenylprop-2-en-1-yl carbonate (444575-90-0) → 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;	74%

isoquinolin-6-ol (7651-82-3) + tert-butyl (1-(o-tolyl)allyl) carbonate → 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 0.133333h; Inert atmosphere; enantioselective reaction;	73%

isoquinolin-6-ol (7651-82-3) + tert-butyl (1-(4-iodophenyl)allyl) carbonate → C18H14INO

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;	72%

isoquinolin-6-ol (7651-82-3) → 6-fluoroisoquinoline (1075-11-2)

Conditions	Yield
With N,N'-1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-2,2-difluoroimidazolidine; cesium fluoride In 1,4-dioxane at 23 - 110℃; for 24.5h; Inert atmosphere;	71%

isoquinolin-6-ol (7651-82-3) + (+/-)-1-(4'-bromophenyl)prop-2-en-1-yl tert-butyl carbonate (1073277-21-0) → C18H14BrNO

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;	71%

isoquinolin-6-ol (7651-82-3) + 1-([1,1'-biphenyl]-4-yl)allyl tert-butyl carbonate → C24H19NO

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;	71%

isoquinolin-6-ol (7651-82-3) + tert-butyl (1-(naphthalene-2-yl)allyl) carbonate → C22H17NO

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;	71%

isoquinolin-6-ol (7651-82-3) + tert-butyl (1-(3-methoxyphenyl)allyl) carbonate (1073277-24-3) → C19H17NO2

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; dibenzenesulfonamide In methanol at 25℃; for 9h; Inert atmosphere; enantioselective reaction;	68%

isoquinolin-6-ol (7651-82-3) + ammonium hydroxide (1336-21-6) → 6-isoquinolinamine (23687-26-5)

Conditions	Yield
In water	67%

isoquinolin-6-ol (7651-82-3) + (+/-)-1-(4'-bromophenyl)prop-2-en-1-yl tert-butyl carbonate (1073277-21-0) → C18H14BrNO

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 0.166667h; Inert atmosphere; enantioselective reaction;	66%

isoquinolin-6-ol (7651-82-3) + tert-butyl (1-(4-iodophenyl)allyl) carbonate → C18H14INO

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 0.166667h; Inert atmosphere; enantioselective reaction;	65%

Upstream product

• 67-56-1 methanol 
• 34784-05-9 6-bromo-isoquinoline 
• 52986-70-6 6-methoxyisoquinoline 

Downstream Products

• 23687-26-5 6-isoquinolinamine 
• 160452-18-6 6,6-Diphenyl-6H-5-oxa-2-aza-phenanthrene 
• 918488-41-2 5-chloro-6-hydroxyisoquinoline 
• 915714-67-9 (S)-5-isoquinolin-6-yloxy-4-N-Boc-1-N'-Z-pentane-1,4-diamine 
• 1269630-47-8 C₂₁H₂₂N₂O 
• 1269630-46-7 C₂₁H₂₂N₂O 
• 1075-11-2 6-fluoroisoquinoline 
• 444575-90-0 (R)-(+)-tert-butyl 1-phenylprop-2-en-1-yl carbonate 

Relevant articles and documents

Time-dependent enantiodivergent synthesis via sequential kinetic resolution

The preparation of both enantiomers of chiral molecules is among the most fundamental tasks in organic synthesis, medicinal chemistry and materials science. Achieving this goal typically requires reversing the absolute configuration of the chiral component employed in the reaction system that is being used. The task becomes challenging when the natural source of the chiral component is not available in both configurations. Herein, we report a time-dependent enantiodivergent synthesis, in which an Ir-catalysed allylic substitution reaction uses one catalyst sequentially to promote two kinetic resolution reactions, enabling the synthesis of both enantiomers of the product using the same enantiomer of a chiral catalyst. The appropriate permutation of individual reaction rates is essential for the isolation of the chiral products in opposite configurations with high enantiopurity when quenched at different reaction times. This work provides an alternative solution for the preparation of both enantiomers of chiral molecules. [Figure not available: see fulltext.].

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