15248-39-2

Basic information

• Product Name: 6,7-DIMETHOXYISOQUINOLINE
• Synonyms: 6,7-DIMETHOXYISOQUINOLINE;6,7-Dimethoxyisoquinoline 96%;6,7-DiMethoxyisoquinoline 9;6,7-Dimethoxyisoquinoline96%;backebergine
• CAS NO: 15248-39-2
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• Product Categories: blocks;Heterocycles;Quinolines
• Mol File: 15248-39-2.mol
• Article Data: 38

Chemical Properties

• Melting Point: 92.0 to 96.0 °C
• Boiling Point: 158°C/0.9mmHg(lit.)
• Flash Point: 117.2°C
• Appearance: Off-white solid
• Density: 1.148g/cm³
• Vapor Pressure: 0.000614mmHg at 25°C
• Refractive Index: 1.589
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 6.25±0.10(Predicted)
• CAS DataBase Reference: 6,7-DIMETHOXYISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-DIMETHOXYISOQUINOLINE(15248-39-2)
• EPA Substance Registry System: 6,7-DIMETHOXYISOQUINOLINE(15248-39-2)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 15248-39-2(Hazardous Substances Data)

Usage

Description

6,7-Dimethoxyisoquinoline is an organic compound that belongs to the class of isoquinolines, characterized by the presence of two methoxy substituents at positions 6 and 7. It is a versatile molecule with potential applications in various fields due to its unique chemical properties.

Uses

Used in Chemical Synthesis:
6,7-Dimethoxyisoquinoline is used as an organocatalyst for the chemoselective O-tert-butoxycarbonylation of phenols. This application takes advantage of its ability to facilitate specific chemical reactions, leading to the formation of desired products with high selectivity and efficiency.
In the pharmaceutical industry, 6,7-dimethoxyisoquinoline can be used as a key intermediate in the synthesis of various bioactive compounds, including potential drug candidates. Its unique structure allows for further functionalization and modification, making it a valuable building block in the development of new medications.
Additionally, 6,7-dimethoxyisoquinoline may find applications in the field of materials science, where its properties can be exploited to design and synthesize novel materials with specific characteristics, such as improved stability, reactivity, or selectivity.

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 3773, 1957 DOI: 10.1021/ja01571a043Synthesis, p. 288, 1974Tetrahedron Letters, 13, p. 4789, 1972

InChI:InChI=1/C11H11NO2/c1-13-10-5-8-3-4-12-7-9(8)6-11(10)14-2/h3-7H,1-2H3

Upstream product

• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 91569-96-9 6,7-dimethoxy-isoquinoline-1-carboxylic acid 
• 58163-19-2 dimethoxy-3,4 benzylideneaminoacetal diethylique 
• 32871-88-8 N-(3,4-dimethoxybenzyl)aminoacetaldehyde diethyl acetal 
• 522-57-6 papaveraldine 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 39964-92-6 N-(3,4-dimethoxybenzyl)-N-(2,2-dimethoxyethyl)-4-methylbenzenesulfonamide 
• 40243-67-2 5,6-dimethoxy-1H-indene 
• 121607-64-5 2-ethenyl-4,5-dimethoxybenzaldoxime 
• 2328-12-3 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride 
• 140696-57-7 Benzoic acid (R)-((S)-2-benzoyl-6,7-dimethoxy-1,2-dihydro-isoquinolin-1-yl)-(3,4-dimethoxy-phenyl)-methyl ester 
• 78004-25-8 N-<2-Hydroxy-2-(3,4-dimethoxyphenyl)ethyl>formamide 
• 86727-46-0 [[(2,2-Dimethoxy-ethyl)-ethoxycarbonyl-amino]-(3,4-dimethoxy-phenyl)-methyl]-phosphonic acid dimethyl ester 
• 121607-68-9 2-ethenyl-4,5-dimethoxybenzaldoxime O-methyl ether 

Downstream Products

• 64434-29-3 2-benzyl-6,7-dimethoxyisoquinolin-1(2H)-one 
• 50299-95-1 2-benzoyl-1-cyano-6,7-dimethoxy-1,2-dihydroisoquinoline 
• 3428-75-9 N-methyl-6,7-dimethoxyisoquinolinium iodide 
• 138977-21-6 6,7-Dimethoxy-1-methyl-1H-isoquinoline-2-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 77287-52-6 2--6,7-dimethoxy-1,2-dihydroisoquinaldonitrile 
• 93631-45-9 6,7-Dimethoxy-2-ethoxycarbonyl-1,2-dihydroisoquinaldonitrile 
• 21560-29-2 1-chloro-6,7-dimethoxyisoquinoline 
• 490-11-9 3,4-pyridinecarboxylic acid 
• 577-68-4 m-hemipinic acid 
• 102003-17-8 6,7-dimethoxy-2-(4-methoxy-benzoyl)-1,2-dihydro-isoquinoline-1-carbonitrile 
• 102318-55-8 6,7-dimethoxy-2-veratroyl-1,2-dihydro-isoquinoline-1-carbonitrile 
• 102311-65-9 (+/-)-2-trans-cinnamoyl-6,7-dimethoxy-1,2-dihydro-isoquinoline-1-carbonitrile 

Relevant articles and documents

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Reusable, homogeneous water soluble photoredox catalyzed oxidative dehydrogenation of N-heterocycles in a biphasic system: Application to the synthesis of biologically active natural products

Herein, a simple and efficient method for the oxidative dehydrogenation (ODH) of tetrahydro-β-carbolines, indolines and tetrahydro-(iso)quinolines is described using a reusable, homogeneous cobalt-phthalocyanine photoredox catalyst in a biphasic medium. A biphasic system offers an advantage of easy separation of the product and an efficient reusability of the homogeneous photoredox catalyst. Also, the current system significantly helps to overcome the solubility issue of the substrate and catalyst at room temperature. Its potential applications to organic transformations are demonstrated by the synthesis of various biologically active N-heterocycles such as indoles, (iso)quinolines and β-carbolines and natural products such as eudistomin U, norharmane, and harmane and precursors to perlolyrine and flazin. Without isolation and purification, the catalyst solution can be reused up to 5 times with almost comparable reactivity. Furthermore, the efficiency of the reaction was demonstrated on a gram scale. To the best of our knowledge, this is the first report on ODH reactions using a non noble, reusable and homogeneous cobalt photoredox catalyst under environmentally friendly conditions.

A Visible-Light Promoted Amine Oxidation Catalyzed by a Cp*Ir Complex

Through a rapid screening of Cp*Ir complexes based on a turn-on type fluorescence readout, a [Cp*Ir(dipyrido[3,2-a : 2’,3’-c]phenazine)Cl]+ complex was found to catalyze the blue-light promoted dehydrogenation of N-heterocycles under physiological conditions. In the dehydrogenation of tetrahydroisoquinolines, the catalyst preferentially yielded the monodehydrogenated product, accompanying H2O2 generation. We surmise that this mechanism may be reminiscent of flavin-dependent oxidases.