180386-76-9

Basic information

• Product Name: 1-[(3,4-dimethoxyphenyl)(methoxy)methyl]-6,7-dimethoxyisoquinoline
• Synonyms: Isoquinoline,1-[(3,4-dimethoxyphenyl)methoxymethyl]- 6,7-dimethoxy-
• CAS NO: 180386-76-9
• Molecular Formula: C₂₁H₂₃NO₅
• Molecular Weight: 369.411
• Mol File: 180386-76-9.mol

Chemical Properties

• Boiling Point: 493.4°C at 760 mmHg
• Flash Point: 175.4°C
• Density: 1.169g/cm³
• Vapor Pressure: 2.13E-09mmHg at 25°C
• Refractive Index: 1.576
• CAS DataBase Reference: 1-[(3,4-dimethoxyphenyl)(methoxy)methyl]-6,7-dimethoxyisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(3,4-dimethoxyphenyl)(methoxy)methyl]-6,7-dimethoxyisoquinoline(180386-76-9)
• EPA Substance Registry System: 1-[(3,4-dimethoxyphenyl)(methoxy)methyl]-6,7-dimethoxyisoquinoline(180386-76-9)

Safety Data

• Hazardous Substances Data: 180386-76-9(Hazardous Substances Data)

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 15248-39-2 6,7-dimethoxyisoquinoline 
• 67-56-1 methanol 
• 1126908-84-6 1-[dichloro-(3,4-dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline 
• 482-76-8 papaverinol 
• 74-88-4 methyl iodide 

Relevant articles and documents

A divergent approach to benzylisoquinoline-type and oxoaporphine alkaloids via regioselective direct ring metalation of alkoxy isoquinolines

Methoxy- and benzyloxy-substituted isoquinolines are regioselectively metalated at C-1 with the Knochel-Hauser base, subsequent trapping with aromatic aldehydes gives aryl(isoquinolin-1-yl)carbinols as building blocks for divergent syntheses of different types of benzylisoquinoline alkaloids. Photochemical cyclization of ortho-bromo analogues under reductive conditions gives oxoaporphine alkaloids. Nine benzylisoquinoline alkaloids and two oxoaporphine alkaloids were obtained in two or three steps from appropriate isoquinolines.

New synthesis of 1-[(3,4-dimethoxyphenyl)methoxymethyl]-6,7-dimethoxyisoquinoline (setigerine), a naturally occurring alkaloid, and some derivatives of papaverine

A novel and improved synthetic route for the preparation of the new alkaloid setigerine, isolated from Papaver setigerum DC, and some new 3,4-dihydropapaverine and papaverine derivatives is reported. This method is based on the side chain chlorination of 1-benzyl-3,4-dihydroisoquinolines using N-chlorosuccinimide (NCS) and subsequent reaction with sodium methoxide in methanol to give the corresponding isoquinolines.