42398-73-2

Basic information

• Product Name: 6-Methylisoquinoline
• Synonyms: 6-Methylisoquinoline 98%;6-Methylisoquinoline;Isoquinoline, 6-methyl-;6-Methylisoquinoline ,98%;3,4,4-trimethylpentan-2-one
• CAS NO: 42398-73-2
• Molecular Formula: C₁₀H₉N
• Molecular Weight: 143.19
• EINECS: 255-794-3
• Product Categories: blocks;Heterocycles;Quinolines;Heterocyclic Series;Quinoline&Isoquinoline;Isoquinoline Derivertives
• Mol File: 42398-73-2.mol

Chemical Properties

• Melting Point: 85.5°C
• Boiling Point: 246.29°C (estimate)
• Flash Point: 112.269 °C
• Appearance: /
• Density: 1.0584 (estimate)
• Vapor Pressure: 0.014mmHg at 25°C
• Refractive Index: 1.6103 (estimate)
• PKA: 5.85±0.10(Predicted)
• CAS DataBase Reference: 6-Methylisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methylisoquinoline(42398-73-2)
• EPA Substance Registry System: 6-Methylisoquinoline(42398-73-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-24/25
• Hazardous Substances Data: 42398-73-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
6-Methylisoquinoline is used as a reagent for the green preparation of polyfluoroarylated heterocyclic compounds. Its chemical properties allow for efficient and environmentally friendly synthesis processes, making it a preferred choice in the chemical industry for creating these types of compounds.
Used in Pharmaceutical Industry:
6-Methylisoquinoline is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and reactivity contribute to the development of new drugs with potential therapeutic applications.
Used in Research and Development:
6-Methylisoquinoline is utilized as a research compound in academic and industrial laboratories. Its properties make it a valuable tool for studying the synthesis and properties of heterocyclic compounds, as well as for exploring new reaction pathways and mechanisms.
Used in Material Science:
6-Methylisoquinoline can be used as a building block for the development of new materials with specific properties. Its incorporation into various chemical structures can lead to the creation of materials with unique characteristics, such as improved stability, reactivity, or selectivity.

Preparation

A benzene solution (50 ml, CAUTION) of equimolar amounts of p-tolualdehyde (8.4 g, 0.07 mol) and aminoacetaldehyde dimethyl acetal (7.35 g, 0.07 mol) is refluxed overnight into a Dean and Stark trap. The solution is evaporated in vacuo and then twice evaporated again with added benzene and the viscous oil dissolved in dry tetrahydrofuran. This solution is cooled to - 10 °C and 1 equivalent of ethyl chloroformate (7. 1 ml, 0.07 mol) is added with rapid stirring and the mixture stirred for a further 5 minutes. The cooling bath is removed and 1.2 equivalents of trimethyl phosphite ( 10.5 ml, 0.09 mol) is added with stirring. The solution is stirred at room temperature for 1 5 hours and then evaporated t o an oil. The oil is then re-evaporated twice with added toluene to remove traces of trimethyl phosphite. The oil is dissolved in dry dichloromethane, 6 equivalents of titanium(1v) chloride (50 ml, 0.45 mol) is added and the solution refluxed for 36 hours under a drying tube. The cooled solution is shaken with 1 equivalent of aqueous sodium hydroxide solution to neutrality, whereupon titanium(1v) oxide precipitates as a white solid. The filtered organic layer is extracted with 3 M hydrochloric acid, and the extract is washed with dichloromethane, basified strongly with aqueous alkali, and extracted with dichloromethane. This organic extract is dried over anhydrous sodium sulphate and evaporated to afford 6-methylisoquinoline (yield 7 1 %, m.p. 88 °C).

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 3344, 1983 DOI: 10.1021/jo00167a043

InChI:InChI=1/C10H9N/c1-8-2-3-10-7-11-5-4-9(10)6-8/h2-7H,1H3

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 645-36-3 2,2-diethoxy-ethanamine 
• 20232-11-5 6-methyl-1H-indene 
• 1122-62-9 2-acetylpyridine 
• 34784-05-9 6-bromo-isoquinoline 
• 54879-84-4 2-(4-methylbenzylamino)acetaldehyde dimethyl acetal 
• 22483-09-6 2,2-dimethoxyethylamine 
• 54879-70-8 (2,2-Dimethoxy-ethyl)-[1-p-tolyl-meth-(Z)-ylidene]-amine 
• 541-41-3 chloroformic acid ethyl ester 
• 54879-40-2 N-(2,2-Dimethoxy-ethyl)-4-methyl-N-(4-methyl-benzyl)-benzenesulfonamide 
• 86401-98-1 N-(tert-butyl)-N-(4-methyl-benzylidene)-amine 
• 84900-33-4 2,4,6-Trimethyl-benzenesulfonate2-amino-6-methyl-isoquinolinium; 

Downstream Products

• 84900-33-4 2,4,6-Trimethyl-benzenesulfonate2-amino-6-methyl-isoquinolinium; 
• 943606-86-8 6-methyl-5-nitro-N-(3-(trifluoromethyl)phenyl)isoquinoline-1-amine 
• 943606-87-9 6-methyl-N¹-(3-(trifluoromethyl)phenyl)isoquinoline-1,5-diamine 
• 943606-92-6 5-iodo-6-methyl-N-(3-(trifluoromethyl)phenyl)isoquinolin-1-amine 
• 131002-10-3 6-methyl-2H-isoquinolin-1-one 
• 1430217-51-8 (E)-methyl 4-(2-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acryloyl)-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxamido)benzoate 
• 1430216-12-8 (E)-4-(2-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acryloyl)-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxamido)benzoic acid 
• 1338322-19-2 (S)-phenyl 1-((S)-2-(4-methoxyphenyl)-4-methyl-5-oxo-4,5-dihydrooxazol-4-yl)-6-methylisoquinoline-2(1H)-carboxylate 

Relevant articles and documents

Cu(II)-Catalyzed Construction of Heterobiaryls using 1-Diazonaphthoquinones: A General Strategy for the Synthesis of QUINOX and Related P,N Ligands

An efficient and straightforward method was developed for the synthesis of heterobiaryls using easily available N-oxides and diazonaphthoquinones under cheap Cu(II) catalysis. The developed method offered QUINOX and related congeners in a simple manner. A wide scope of important heterobiaryls was achieved with high site selectivity. The synthesized naphthols were transformed into the privileged related P,N ligands. Suitable resolution methods can directly afford the corresponding axially chiral heterobiaryls.

Pd-Catalyzed Alkylation of (Iso)quinolines and Arenes: 2-Acylpyridine Compounds as Alkylation Reagents

The first Pd-catalyzed alkylation of (iso)quinolines and arenes is reported. The readily available and bench-stable 2-acylpyridine compounds were used as an alkylation reagent to form the structurally versatile alkylated (iso)quinolines and arenes. The method affords a convenient pathway for the introduction of alkyl groups into organic molecules.

ISOQUINOLINE-5-CARBOXAMIDE DERIVATIVE HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASE

A compound selected from the group consisting of an isoquinoline-5-carboxamide derivative of formula (I), a pharmaceutically acceptable salt, an isomer, a hydrate and a solvate thereof is effective for the prevention or treatment of diseases associated with abnormal cell growth, which are caused by abnormal activation of a protein kinases.

ISOQUINOLINE-5-CARBOXAMIDE DERIVATIVE HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASE

A compound selected from the group consisting of an isoquinoline-5-carboxamide derivative of formula (I), a pharmaceutically acceptable salt, an isomer, a hydrate and a solvate thereof is effective for the prevention or treatment of diseases associated with abnormal cell growth, which are caused by abnormal activation of a protein kinases.

THIENO[3,2-D]PYRIMIDINE DERIVATIVES HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASES

Provided are a thieno[3,2-d]pyrimidine derivative of formula (I) or a pharmaceutically acceptable salt thereof having inhibitory activity for protein kinase, and a pharmaceutical composition comprising same for prevention and treatment of abnormal cell growth diseases.

THIENO[3,2-d]PYRIMIDINE DERIVATIVES HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASES

Provided are a thieno[3,2-d]pyrimidine derivative of formula (I) or a pharmaceutically acceptable salt thereof having inhibitory activity for protein kinase, and a pharmaceutical composition comprising same for prevention and treatment of abnormal cell growth diseases

Selective inhibitors of the mutant B-Raf pathway: Discovery of a potent and orally bioavailable aminoisoquinoline

The discovery and optimization of a novel series of aminoisoquinolines as potent, selective, and efficacious inhibitors of the mutant B-Raf pathway is presented. The N-linked pyridylpyrimidine benzamide 2 was identified as a potent, modestly selective inhibitor of the B-Raf enzyme. Replacement of the benzamide with an aminoisoquinoline core significantly improved kinase selectivity and imparted favorable pharmacokinetic properties, leading to the identification of 1 as a potent antitumor agent in xenograft models. 2009 American Chemical Society.

RAF KINASE MODULATORS AND METHODS OF USE

The present invention comprises a new class of compounds capable of modulating the activity of Raf kinase and, accordingly, useful for treatment of Raf kinase mediated diseases, including melanomas, tumors and other cancer-related conditions. The compounds have a general Formula (I) wherein each of A1, A2, A3, A4, A5, A6, A7, A8, A9, bond B, X, rings Z1 and Z2, R1 and R3 are defined herein. The invention further comprises pharmaceutical compositions, methods for treatment of Raf kinase mediated diseases, and intermediates and processes useful for the preparation of compounds of the invention.

NITROGEN-CONTAINING BICYCLIC HETEROARYL COMPOUNDS AND METHODS OF USE

The present invention comprises a new class of compounds capable of modulating Raf kinase and, accordingly, useful for treatment of Raf kinase mediated diseases, including melanomas, tumors and other cancer-related conditions. The compounds have Formula (I) wherein R1 is Formula (II), (III) or (IV) and A1, A2, A3, A4, X, Z, Z', R1, R2, R3, R4, R5 and R6 are defined herein. The invention further comprises pharmaceutical compositions, methods for treatment of Raf kinase mediated diseases, and intermediates and processes useful for the preparation of compounds of the invention.

Synthesis and properties of novel stilbazolium analogues as second-order nonlinear optical chromophores

This study synthesized a series of methoxystilbazolium analogues with π-conjugation extended by attaching a fused aromatic ring, i.e., 6-styrylisoquinolinium and 4-[2-(2-naphthyl)ethenyl]pyridinium derivatives with methoxy substituents. We evaluated their transition energies (EegS) and second-order hyperpolarizabilities (βs) experimentally using their absorption spectra and a hyper-Rayleigh scattering measurement, respectively. Subsequently, we calculated βs using the MOPAC PM3 method. These values were compared with those of 4-[4-(4-methoxyphenyl)-1,3-butadienyl]pyridinium derivative, which is a stilbazolium analogue with π-conjugation that is simply extended by an increase of the double-bond number between two aromatic rings. This study clarified that the fused-ring systems possess large βs, irrespective of their relatively short absorption wavelengths, compared to the double-bond elongation system.