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

Uses

6,7-Dimethoxyisoquinoline is used as an organocatalyst in the chemoselective O-tert-butoxycarbonylation of phenols.

Definition

ChEBI: A member of the class of isoquinolines carrying two methoxy substituents at positions 6 and 7.

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 
• 32871-88-8 N-(3,4-dimethoxybenzyl)aminoacetaldehyde diethyl acetal 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 39964-92-6 N-(3,4-dimethoxybenzyl)-N-(2,2-dimethoxyethyl)-4-methylbenzenesulfonamide 
• 121607-64-5 2-ethenyl-4,5-dimethoxybenzaldoxime 
• 140696-57-7 Benzoic acid (R)-((S)-2-benzoyl-6,7-dimethoxy-1,2-dihydro-isoquinolin-1-yl)-(3,4-dimethoxy-phenyl)-methyl ester 
• 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 
• 52095-39-3 2-ethenyl-4,5-dimethoxybenzaldehyde 
• 14165-82-3 1,2,3,4-tetrahydro-6,7-dimethoxy-2-[(4-methylphenyl)sulfonyl]isoquinoline 
• 121607-72-5 2-ethenyl-4,5-dimethoxybenzaldoxime O-benzyl ether 
• 78004-25-8 N-<2-Hydroxy-2-(3,4-dimethoxyphenyl)ethyl>formamide 
• 2328-12-3 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride 
• 40243-67-2 5,6-dimethoxy-1H-indene 

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 
• 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 
• 6075-61-2 6,7-Dimethoxy-1,2-dimethylisoquinoliniumiodide 
• 93631-46-0 6,7-Dimethoxy-2-ethoxycarbonyl-1-methyl-1,2-dihydroisoquinaldonitrile 
• 490-53-9 (+/-)-carnegine 
• 486-99-7 (6,7-dimethoxy-1,2,3,4-tetrahydro-1-isoquinolyl)methanol 

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.

One-Pot Synthesis of Papaverine Hydrochloride and Identification of Impurities

Abstract: A one-pot synthesis of papaverine hydrochloride with 99.6% purity was performed using xylene as solvent for the entire process. The critical parameters of each step, as well as the impurities generated, were identified. The overall yield was improved to 63%. The proposed synthetic procedure is suitable for industrial production.