16535-89-0

Basic information

• Product Name: 1-METHYLISOQUINOLIN-3-OL
• Synonyms: 1-METHYLISOQUINOLIN-3-OL;3-Hydroxy-1-methylisoquinoline
• CAS NO: 16535-89-0
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.2
• Product Categories: API intermediates
• Mol File: 16535-89-0.mol

Chemical Properties

• Melting Point: 204 °C (decomp)(Solv: ethanol (64-17-5))
• Boiling Point: 507.3 °C at 760 mmHg
• Flash Point: 296.6 °C
• Appearance: /
• Density: 1.18 g/cm³
• Storage Temp.: 2-8°C
• PKA: 11.12±0.40(Predicted)
• CAS DataBase Reference: 1-METHYLISOQUINOLIN-3-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYLISOQUINOLIN-3-OL(16535-89-0)
• EPA Substance Registry System: 1-METHYLISOQUINOLIN-3-OL(16535-89-0)

Safety Data

• Hazardous Substances Data: 16535-89-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Methylisoquinolin-3-ol is used as a key building block for the synthesis of various pharmaceuticals, contributing to the development of new drugs with diverse therapeutic applications.
Used in Agrochemical Industry:
1-Methylisoquinolin-3-ol is used as a precursor in the production of agrochemicals, aiding in the creation of compounds that can enhance crop protection and yield.
Used in Antioxidant Applications:
1-Methylisoquinolin-3-ol is used as an antioxidant, leveraging its potential to combat oxidative stress and protect cells from damage, which can be beneficial in various health and industrial applications.
Used in Anti-Inflammatory Applications:
1-Methylisoquinolin-3-ol is used as an anti-inflammatory agent, capitalizing on its capacity to reduce inflammation, which can be advantageous in the treatment of various conditions and in cosmetic formulations.
Overall, 1-Methylisoquinolin-3-ol's versatility and potential applications across different industries make it a compound of significant interest in scientific and industrial research and development.

Upstream product

• 16535-88-9 (2-acetyk-phenyl)-acetic acid methyl ester 
• 173417-10-2 2-[2-(1,1-Dimethoxy-ethyl)-phenyl]-acetamide 
• 58422-85-8 (2-acetyl-phenyl)-acetonitrile 
• 117330-48-0 N-(1-phenylethyl)-2,2-diethoxyacetamide 
• 50777-64-5 2-(2-bromophenyl)-2-methyl-1,3-dioxolane 

Downstream Products

• 189816-06-6 3-Phenyl-isoquinoline-1-carbaldehyde 

Relevant articles and documents

Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of 1,3-Disubstituted Isoquinolines

The development of a general method utilizing a hydroxymethyl directing group for asymmetric hydrogenation of 1,3-disubstituted isoquinolines to provide chiral 1,2,3,4-tetrahydroisoquinolines is reported. The reaction, which utilizes [Ir(cod)Cl]2 and a commercially available chiral xyliphos ligand, proceeds in good yield with high levels of enantioselectivity and diastereoselectivity (up to 95% ee and >20:1 dr) on a range of differentially substituted isoquinolines. Directing-group studies demonstrate that the hydroxymethyl functional group at the C1 position is more efficient at enabling hydrogenation in comparison to other substituents, although high levels of enantioselectivity were conserved across a variety of polar and nonpolar functional groups. By utilization of the generated chiral β-amino alcohol as a functional handle, the synthetic utility is further highlighted via the synthesis of 1,2-fused oxazolidine, oxazolidinone, and morpholinone tetrahydroisoquinolines in one step. Additionally, a non-natural analogue of the tetrahydroprotoberberine alkaloids was successfully synthesized.

Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4- naphthoquinones via one-pot aryne acyl-alkylation/condensation

A convenient method is disclosed for the synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from β-ketoesters using a one-pot aryne acyl-alkylation/condensation procedure. When performed in conjunction with a one-step method for the synthesis of the β-ketoester substrates, this method provides a new route to these polyaromatic structures in only two steps from commercially available carboxylic acid starting materials. The utility of this approach is demonstrated in the synthesis of the atropisomeric P,N-ligand, QUINAP. The Royal Society of Chemistry 2009.

Photochemical Hydrolysis of o-Acetylphenylacetonitriles

Irradiation of 1 and its methyl derivative 10a (λ>280 nm) in methanol leads to photohydrolysis of the nitrile group and formation of the related ketal amides 3 and 11a, respectively.Similar treatment of the dimethyl derivative 10b and of the parent nitrile 13 fails to yield corresponding products of hydrolysis.A mechanism is proposed for these novel hydrolyses.

Macropolycyclic rare earth complexes and application as fluorescent tracers

The invention relates to macropolycyclic rare earth complexes, namely cryptates which are useful as fluorescent tracers.

Synthesis and Characterisation of the Sodium and Lithium Cryptates of Macrobicyclic Ligands Incorporating Pyridine, Bipyridine, and Biisoquinoline Units

Synthetic procedures have been developed for the preparation of sodium and lithium cryptates of the macrobicyclic ligands 1-11 containing pyridine, bipyridine, and biisoquinoline groups.They involve stepwise construction of the bicyclic system as well as direct macrobicyclisation procedures (Scheme 1) and give access to both symmetrical and dissymmetrical structures.Marked cation template effects have been found that facilitate the cyclisation processes.The ligands 1-11 were isolated as their cryptates with Na+ or Li+ cations.