4594-71-2

Basic information

• Product Name: 2-Methyl-1(2H)-isoquinolone
• Synonyms: 2-Methyl-1(2H)-isoquinolone;2-Methyl-1(2H)-isoquinolinone;2-Methyl-1,2-dihydroisoquinoline-1-one;2-Methylisoquinolin-1(2H)-one;1(2H)-Isoquinolinone, 2-methyl-;N-Methylisocarbostyril;Isocarbostyril, 2-methyl-
• CAS NO: 4594-71-2
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.19
• Mol File: 4594-71-2.mol

Chemical Properties

• Melting Point: 105-106 °C
• Boiling Point: 307.6 °C at 760 mmHg
• Flash Point: 145.2 °C
• Appearance: /
• Density: 1.16 g/cm³
• Vapor Pressure: 0.000719mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -2.17±0.70(Predicted)
• CAS DataBase Reference: 2-Methyl-1(2H)-isoquinolone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-1(2H)-isoquinolone(4594-71-2)
• EPA Substance Registry System: 2-Methyl-1(2H)-isoquinolone(4594-71-2)

Safety Data

• Hazardous Substances Data: 4594-71-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
2-Methyl-1(2H)-isoquinolone is utilized as a compound of interest in the development of new medications due to its potential neuroprotective and anti-inflammatory effects. It is particularly considered for the treatment of neurological disorders and inflammatory conditions, given its ability to modulate biological responses within the body.
Used in the Synthesis of Bioactive Compounds:
As a versatile building block, 2-Methyl-1(2H)-isoquinolone is employed in the synthesis of various bioactive compounds. Its structural features allow for the creation of a wide range of molecules with potential therapeutic applications, contributing to the advancement of medicinal chemistry.

InChI:InChI=1/C10H9NO/c1-11-7-6-8-4-2-3-5-9(8)10(11)12/h2-7H,1H3

Upstream product

• 119-65-3 isoquinoline 
• 80-48-8 methyl p-toluene sulfonate 
• 77-78-1 dimethyl sulfate 
• 3947-77-1 2-methylisoquinolinium iodide 
• 491-30-5 1-isoquinolone 
• 74-88-4 methyl iodide 
• 23724-93-8 1-Methoxyisochinolin 
• 59168-23-9 3-Hydroxy-2-methyl-1-oxotetrahydroisoquinoline 
• 54410-18-3 2-methylisoquinolinium bromide 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 491-30-5 1-hydroxyisoquinoline 
• 872-36-6 vinylene carbonate 
• 1315257-09-0 N-methyl-2,3,4,5,6-pentadeuteriobenzamide 
• 88070-48-8 N-methylbenzamide 

Downstream Products

• 14945-74-5 2-methyl-1(2H)-thioisoquinolone 
• 6772-65-2 2-methyl-3,4-dihydro-2H-isoquinolin-1-one 
• 19493-44-8 1-chloroisoquinoline 
• 55577-53-2 1-iodo-2-methyl-isoquinolinium; iodide 
• 54931-72-5 2-methyl-4-(phenylethynyl)isoquinolin-1(2H)-one 
• 33930-63-1 4-bromo-2-methyl-1,2-dihydroisoquinolin-1-one 
• 1349798-31-7 C₂₄H₂₈N₂O₂ 
• 21640-33-5 2-methyl-isoquinoline-1,3,4-trione 

Relevant articles and documents

Ultrasound-promoted synthesis of quinolone and isoquinolone derivatives

Quinolinium and isoquinolinium salts are easily oxidized by potassium tert-butylate in tert-butanol under ultrasonic irradiation yielding quinolones and isoquinolones. Compared to the methods previously known, the main advantages of our process are shorter reaction times, easier work-up and good to quantitative yields.

Carbon-13 NMR Spectra of Isocoumarin, N-Methyl-1(2H)-isoquinolinone and Related Compounds

The 13C NMR spectra of isocoumarin, N-methyl-1(2H)-isoquinolinone and 14 of their 3- and/or 4-substituted derivatives were measured and assigned with the aid of various spectral techniques.The values of the one-bond and some of the long-range 13C-1H coupling constants are reported.The effect of substitution on the 13C chemical shifts is discussed.

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

Harnessing selective PET and EnT catalysis by chlorophyll to synthesizeN-alkylated quinoline-2(1H)-ones, isoquinoline-1(2H)-ones and 1,2,4-trioxanes

Photocatalytic syntheses of quinoline-2(1H)-ones, isoquinoline-1(2H)-ones and 1,2,4-trioxanes were achieved by selective photo-induced electron transfer (PET) and energy transfer (EnT), respectively, by chlorophyll under visible light irradiation. Quinoli

Light-driven selective aerobic oxidation of (iso)quinoliniums and related heterocycles

Selective C1-H/C4-H carbonylation of N-methylene iminium salts, catalyzed by visible-light photoredox and oxygen in the air, has been reported. A ruthenium complex acts as a chemical switch to conduct two different reaction pathways and to afford two diff

I2-Promoted Direct C?H Sulfenylation of Isoquinolin-1(2H)-ones with Sulfonyl Chlorides

A simple, efficient, and green method for the iodine-promoted regioselective C-4 sulfenylation of isoquinolin-1(2H)-ones using commercially available aryl sulfonyl chlorides as the sulfur source was described under metal- and solvent-free conditions. The reaction proceeded smoothly under simple conditions to obtain 4-arylthioisoquinolin-1(2H)-ones in moderate to good yields, and showed high regioselectivity, broad substrate scope, and good functional group tolerance. A radical reaction mechanism involving ArS. radicals as key intermediates is proposed for the present transformation.

Iodine-catalyzed sulfuration of isoquinolin-1(2H)-ones applying ethyl sulfinates

An efficient sulfuration of isoquinolin-1(2H)-ones at the C-4 position is reported by employing ethyl sulfinates, and the corresponding products are obtained in moderate to excellent yields in the presence of iodine. This synthetic strategy provides a range of thioether-isoquinolin-1(2H)-ones while tolerating a number of functional groups on the isoquinoline nitrogen atom and benzene ring. In addition, pyridin-2(1H)-one is also reacted smoothly and afforded the corresponding thioether product in moderate yield. A plausible mechanism is suggested based on the preliminary mechanistic studies.

Visible-Light-Induced Controlled Oxidation of N-Substituted 1,2,3,4-Tetrahydroisoquinolines for the Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones and Isoquinolin-1(2H)-ones

A visible light-rose bengal-TBHP mediated, controlled oxidation of N-substituted 1,2,3,4-tetrahydroisoquinolines is developed for the synthesis of 3,4-dihydroisoquinolin-1(2H)-ones and isoquinolin-1(2H)-ones. The present method feature's a broad substrate scope, good functional group tolerances, and the products were prepared in good to excellent yields. The developed methodology further demonstrated in the synthesis of isoindolo[2,1-b] isoquinolin-5(7H)-one (topoisomerase-I inhibitor). (Figure presented.).

PROCESS FOR THE PREPARATION OF BROMODOMAIN INHIBITOR

The present invention provides processes of synthesis and purification of a bromodomain inhibitor, Compound 1, which compound includes crystalline forms, amorphous forms, solvates, and hydrates thereof. Embodiments of the disclosure relate to chemical syn

SUBSTITUTED ARYLMETHYLUREAS AND HETEROARYLMETHYLUREAS, ANALOGUES THEREOF, AND METHODS USING SAME

The present invention includes substituted arylmethyl ureas and heteroarylmethyl-ureas, and compositions comprising the same, that can be used to treat or prevent hepatitis B virus (HBV) infections in a patient.