522-57-6

Basic information

• Product Name: (6,7-dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone
• Synonyms: (6,7-dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone;papaveraldine;6,7-dimethoxy-1-veratroylisoquinoline;xanthaline;(6,7-Dimethoxyisoquinolin-1-yl)(3,4-dimethoxyphenyl) ketone;(6,7-dimethoxy-1-isoquinolyl)-(3,4-dimethoxyphenyl)methanone
• CAS NO: 522-57-6
• Molecular Formula: C₂₀H₁₉NO₅
• Molecular Weight: 353.36856
• EINECS: 208-331-4
• Mol File: 522-57-6.mol
• Article Data: 34

Chemical Properties

• Melting Point: 208-209°
• Boiling Point: 486.8°C (rough estimate)
• Flash Point: 279.1°C
• Appearance: /
• Density: 1.2976 (rough estimate)
• Vapor Pressure: 1.21E-11mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 2.04±0.40(Predicted)
• CAS DataBase Reference: (6,7-dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone(CAS DataBase Reference)
• NIST Chemistry Reference: (6,7-dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone(522-57-6)
• EPA Substance Registry System: (6,7-dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone(522-57-6)

Safety Data

• Hazardous Substances Data: 522-57-6(Hazardous Substances Data)

Usage

Description

(6,7-Dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone is a chemical compound characterized by its unique molecular structure, which features two aromatic rings connected by a carbonyl group. The isoquinolyl ring is substituted with two methoxy groups at the 6 and 7 positions, while the phenyl ring is substituted with two methoxy groups at the 3 and 4 positions. (6,7-dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone is known for its potential applications in various fields due to its chemical properties.

Uses

Used in Pharmaceutical Industry:
(6,7-Dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to serve as a building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
(6,7-dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone is also used as a research tool in the field of organic chemistry. It can be employed to study the reactivity of different functional groups and to explore new synthetic pathways for the preparation of complex organic molecules.
Used in Material Science:
(6,7-Dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone may have potential applications in the development of new materials, such as organic semiconductors or optoelectronic devices, due to its electronic properties and the possibility of modifying its structure through chemical synthesis.
Used in Papaverine Production:
As an impurity in the production of Papaverine (P190500), a smooth muscle relaxant found in opium, (6,7-dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone may play a role in the synthesis process or be a byproduct of the reaction. Its presence in the final product could have implications for the pharmacological activity or safety profile of Papaverine, and further research may be necessary to understand its effects.

InChI:InChI=1/C20H19NO5/c1-23-15-6-5-13(10-16(15)24-2)20(22)19-14-11-18(26-4)17(25-3)9-12(14)7-8-21-19/h5-11H,1-4H3

Upstream product

• 482-76-8 papaverinol 
• 17366-51-7 (Z)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 3947-79-3 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-3,4-dihydroisoquinolinium iodide 
• 61-25-6 papaverine hydrochloride 
• 83511-44-8 1-(2'-amino-4',5'-dimethoxy-α-oxobenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 58-74-2 Papaverine 
• 7732-18-5 water 
• 15248-39-2 6,7-dimethoxyisoquinoline 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 139-76-4 N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide 
• 6957-27-3 3,4-dihydropapaverine 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 4732-70-1 3,4-dimethoxyphenylglyoxylic acid 

Downstream Products

• 91790-53-3 1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4-dimethoxybenzyl)isoquinoline 
• 482-76-8 papaverinol 
• 17656-58-5 (6,7-dimethoxy-isoquinolin-1-yl)-(3,4-dimethoxy-phenyl)-methanone oxime 
• 61-25-6 papaverine hydrochloride 
• 855427-50-8 papaveraldine thiosemicarbazone 
• 58024-45-6 1-(6,7-dimethoxyisoquinolin-1-yl)-1-(3,4-dimethoxyphenyl)ethylene 
• 15248-39-2 6,7-dimethoxyisoquinoline 
• 93-07-2 Veratric acid 
• 58-74-2 Papaverine 
• 58024-46-7 (6,7-dimethoxyisoquinolin-1-yl)-(3,4-dimethoxyphenyl)phenylcarbinol 
• 58024-44-5 6,7-dimethoxy-1-(3',4'-dimethoxy-α-hydroxy-α-methylbenzyl)isoquinoline 
• 40766-58-3 1-(6,7-dimethoxy-isoquinolin-1-yl)-1-(3,4-dimethoxy-phenyl)-4-morpholin-4-yl-butan-1-ol 
• 13074-31-2 Tetrahydropapaverine 
• 20323-72-2 (6,7-dimethoxyisoquinolin-1-yl)(4,5-dimethoxy-2-nitrophenyl)-methanone 

Relevant articles and documents

Hypervalent iodine oxidation products of papaverine and its microbial metabolites

(Diacetoxyiodo)benzene (DAIB) oxidizes papaverine to papaveraldine (2) and to 1-hydroxymethyl-6,7-dimethoxyisoquinoline (3), whereas 3'-desmethylpapaverine and 6-dexmethylpapaverine are converted into novel products (4) and (5), respectively.

Metal- And additive-free C-H oxygenation of alkylarenes by visible-light photoredox catalysis

A metal- and additive-free methodology for the highly selective, photocatalyzed C-H oxygenation of alkylarenes under air to the corresponding carbonyls is presented. The process is catalyzed by an imide-acridinium that forms an extremely strong photooxidant upon visible light irradiation, which is able to activate inert alkylarenes such as toluene. Hence, this is an easy to perform, sustainable and environmentally friendly oxidation that provides valuable carbonyls from abundant, readily available compounds.

Development of Pd(OAc)2-catalyzed tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds: Concise synthesis of 1-aroylisoquinoline, oxoaporphine, and 8-oxyprotoberberine alkaloids

A catalytic tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds is developed. This tandem oxidation is applied to two-step total syntheses of papaveraldine and pulcheotine A. Additionally, the total synthesis of liriodenine is achieved in six steps from homopiperonyl alcohol and 2-bromophenylacetonitrile by applying this catalytic tandem oxidation. Moreover, the direct conversion of xylopinine to 8-oxypseudopalmatine in a 76% yield demonstrates the versatility of this catalytic reaction.

Electrochemical benzylic oxidation of C-H bonds

Oxidized products have become increasingly valuable as building blocks for a wide variety of different processes and fine chemistry, especially in the benzylic position. We report herein a sustainable protocol for this transformation through C-H functionalization and is performed using electrochemistry as the main power source and tert-butyl hydroperoxide as the radical source for the C-H abstraction. The temperature conditions reported here do not increase above 50 °C and use an aqueous-based medium. A broad substrate scope is explored, along with bioactive molecules, to give comparable and increased product yields when compared to prior reported literature without the use of electrochemistry.