7651-81-2

Basic information

• Product Name: 3-Hydroxyisoquinoline
• Synonyms: 3-HYDROXYISOQUINOLINE;3-ISOQUINOLINOL;Isoquinolin-3-ol;3-Hydorxyisoquinoline;Isoquinolin-3(2H)-one;Isoquinolin-3-ol, 3-Hydroxy-2-azanaphthalene;3-Hydroxyisoquinoline,99%;2,3-dihydroisoquinolin-3-one
• CAS NO: 7651-81-2
• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.16
• Product Categories: blocks;Quinolines;API intermediates;alcohol
• Mol File: 7651-81-2.mol

Chemical Properties

• Melting Point: 192-194 °C(lit.)
• Boiling Point: 551.9 °C at 760 mmHg
• Flash Point: 319.4 °C
• Appearance: /
• Density: 1.23 g/cm³
• Vapor Pressure: 3.16E-12mmHg at 25°C
• Refractive Index: 1.642
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 11.06±0.20(Predicted)
• BRN: 113230
• CAS DataBase Reference: 3-Hydroxyisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxyisoquinoline(7651-81-2)
• EPA Substance Registry System: 3-Hydroxyisoquinoline(7651-81-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-41
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 7651-81-2(Hazardous Substances Data)

Usage

Uses

Used in Optoelectronics and Lighting Industry:
3-Hydroxyisoquinoline is used as a component in a polymeric mixture for producing white light. Specifically, it is combined with polyvinyl alcohol (PVA) and Nile Red to achieve this effect through F?rster resonance energy transfer, which is a non-radiative dipole-dipole coupling process that can transfer energy between two molecules.
Used in Photochemistry Research:
3-Hydroxyisoquinoline serves as a subject of study for its spectral and photophysical properties in different protic and aprotic solvents. Understanding these properties can contribute to the development of new materials and applications in the field of photochemistry.
Used in Material Science:
The investigation of oxo-hydroxy tautomerism and phototautomerism of 3-HIQ using matrix-isolation techniques can lead to advancements in material science, particularly in the design and synthesis of new compounds with tailored properties for various applications.

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

Upstream product

• 25475-67-6 isoquinolin-3-amine 
• 17507-05-0 1-phenyl-1,4-dihydro-3(2H)-isoquinolinone 
• 34824-58-3 2-(2-bromophenyl)-1,3-dioxolan 
• 34784-02-6 3-bromoisoquinoline 
• 7651-81-2 3-isoquinolinol 
• 1336-21-6 ammonium hydroxide 
• 4252-32-8 N-formylphenylacetamide 

Downstream Products

• 7651-81-2 3-isoquinolinol 
• 102879-33-4 5,6,7,8-tetrahydroisoquinolin-3-ol 
• 1334243-63-8 C₆H₆O₂*C₉H₇NO 
• 86521-11-1 3-trimethylsilylethynylisoquinoline 
• 52067-92-2 2-[2-(aminomethyl)-phenyl]acetic acid hydrochloride 
• 581812-55-7 N-(4-bromobenzyl)-N'-(3-hydroxy-5-isoquinolinyl)urea 
• 1105662-39-2 3-chloro-7,8-dihydroisoquinolin-5(6H)-one 
• 1375352-77-4 2-amino-4-(3-bromo-4,5-dimethoxy-phenyl)-4H-1-oxa-10-aza-phenanthrene-3-carbonitrile 
• 548766-47-8 methyl-phenyl-carbamic acid isoquinolin-3-yl ester 

Relevant articles and documents

Copper-catalyzed hydrolysis of bromoisoquinolines: Preparation of hydroxyisoquinolines

A complex phenomenon was observed in the process of preparing hydroxyisoquinoline through copper-catalyzed hydrolysis of bromoisoquinoline. The copper (II) complexes of hydroxyisoquinoline (L2Cu.5H2O) were characterized by high resolution mass spectra, thermogravimetric analysis, IR, 1H nuclear magnetic resonance (NMR), and 2D-NMR. The Cu (II) complexes were mononuclear and coordinated with oxygen and nitrogen atom of two hydroxyisoquinoline and five water molecules in which a strong hydrogen bond was present. Two optimized methods had been studied to prevent the formation of copper (II) complexes. The isoquinoline with 4, 5, 6, 7, and 8 hydroxyl substitutions were successfully prepared by copper-catalyzed hydrolysis of corresponding bromoisoquinoline and then workup by sodium sulfide or adjusted pH by dry ice or carbon dioxide gas.

Palladium-catalyzed enolate arylation as a key C-C bond-forming reaction for the synthesis of isoquinolines

The palladium-catalyzed coupling of an enolate with an ortho-functionalized aryl halide (an α-arylation) furnishes a protected 1,5-dicarbonyl moiety that can be cyclized to an isoquinoline with a source of ammonia. This fully regioselective synthetic route tolerates a wide range of substituents, including those that give rise to the traditionally difficult to access electron-deficient isoquinoline skeletons. These two synthetic operations can be combined to give a three-component, one-pot isoquinoline synthesis. Alternatively, cyclization of the intermediates with hydroxylamine hydrochloride engenders direct access to isoquinoline N-oxides; and cyclization with methylamine, gives isoquinolinium salts. Significant diversity is available in the substituents at the C4 position in four-component, one-pot couplings, by either trapping the in situ intermediate after α-arylation with carbon or heteroatom-based electrophiles, or by performing an α,α-heterodiarylation to install aryl groups at this position. The α-arylation of nitrile and ester enolates gives access to 3-amino and 3-hydroxyisoquinolines and the α-arylation of tert-butyl cyanoacetate followed by electrophile trapping, decarboxylation and cyclization, C4-functionalized 3-aminoisoquinolines. An oxime directing group can be used to direct a C-H functionalization/bromination, which allows monofunctionalized rather than difunctionalized aryl precursors to be brought through this synthetic route.

Superacidic activation of 1- and 3-isoquinolinols and their electrophilic reactions

Isomeric 1- and 3-isoquinolinols (11 and 12) when activated in CF3SO3H-SbF5 acid system undergo selective ionic hydrogenation with cyclohexane to give 5,6,7,8-tetrahydro-1(2H)- and 5,6,7,8-tetrahydro-3(2H)-isoquinolinones (22 and 27). Under the influence of aluminum chloride similar products were also obtained along with 3,4-dihydro-1(2H)- and 1,4-dihydro-3(2H)-isoquinolinones (23 and 28), respectively. Compounds 11 and 12 also condense with benzene in the presence of aluminum halides, under mild conditions, to give 3,4-dihydro-3-phenyl-1(2H)- and 1,4-dihydro-1-phenyl-3(2H)-isoquinolinones (24 and 29), respectively. Prolonged reaction time or catalysis under strongly acidic HBr-AlBr3 provides an alternative reaction pathway to yield 5,6-dihydro-6,8-diphenyl-1(2H)- and 5,6,7,8-tetrahydro-6,8-diphenyl-3(2H)-isoquinolinones (25 and 30), respectively. Products 24 and 29 were also found to revert back to 11 and 12 in the presence of aluminum halides in o-dichlorobenzene. The mechanism of these intriguing reactions, which involves superelectrophilic dicationic intermediates, is discussed.

Theoretical Description of Solvent Effects. V. The Medium Influence on the Lactim-Lactam Tautomerism of Hydroxyazines

Der Loesungsmitteleffekt auf die Tautomeriegleichgewichte der Titelverbindungen wird mit Hilfe klassischer und quantenchemischer Versionen der Solvatonen- und der Reaktionsfeldtheorie berechnet.In Uebereinstimmung mit dem Experiment ergeben alle getesteten Verfahren eine Gleichgewichtsverschiebung zugunsten der Lactamform.Zur quantitativen Beschreibung dieses Effektes ist jedoch das Reaktionsfeldmodell besser geeignet.

Process for the preparation of 2H-3-isoquinolones

A process for the preparation of 2H-3-isoquinolones having the formula SPC1 Wherein R1 and R2 are each hydrogen, halogen, lower alkyl, lower alkoxy, aryl, haloaryl, alkylaryl or alkoxyaryl; R3 and R4 are each hydrogen, lower alkyl, lower alkoxyalkyl, lower alkenyl, lower alkynyl, cycloalkyl, aryl, aralkyl, or halo-aralkyl, which comprises cyclizing an N-formyl-2-phenyl-acetamide of the formula SPC2 Wherein R1, R2, R3 and R4 have the same meaning as above, with a cyclodehydration agent. Said 2H-3-isoquinolones are useful as starting materials e.g. in the synthesis of 1,4-dihydro-1,4-etheno-isoquinolin-3(2H)-ones which are valuable chemotherapeutic agents in the treatment of disorders of the central nervous system, such as troubles of wakefulness, disorders of equilibrium and vertigo.