76019-13-1

Basic information

• Product Name: 5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• Synonyms: 5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;5,8-Dimethoxy-1,2,3,4-tetrahydroisoquinoline;SKF-72223
• CAS NO: 76019-13-1
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.25
• Mol File: 76019-13-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 353.3°C at 760 mmHg
• Flash Point: 138.3°C
• Appearance: /
• Density: 1.071g/cm³
• Vapor Pressure: 3.62E-05mmHg at 25°C
• Refractive Index: 1.523
• CAS DataBase Reference: 5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline(76019-13-1)
• EPA Substance Registry System: 5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline(76019-13-1)

Safety Data

• Hazardous Substances Data: 76019-13-1(Hazardous Substances Data)

Usage

General Description

5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline is a chemical compound that belongs to the class of tetrahydroisoquinolines. It is a heterocyclic compound containing a six-membered ring with two methoxy groups and a nitrogen atom. 5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline has been studied for its potential pharmaceutical properties, including its role as a serotonin receptor antagonist and its neuroprotective effects. It has also been investigated for its potential use in the treatment of neurodegenerative diseases and as an anti-inflammatory agent. Its unique structure and potential pharmacological activities make it a subject of interest in medicinal chemistry and drug development.

InChI:InChI=1/C11H15NO2/c1-13-10-3-4-11(14-2)9-7-12-6-5-8(9)10/h3-4,12H,5-7H2,1-2H3

Upstream product

• 212184-72-0 N-(2-Benzenesulfinyl-ethyl)-N-(2,5-dimethoxy-benzyl)-formamide 
• 212184-61-7 N-(2,5-Dimethoxy-benzyl)-N-(2-phenylsulfanyl-ethyl)-formamide 
• 212184-79-7 5,8-Dimethoxy-4-phenylsulfanyl-3,4-dihydro-1H-isoquinoline-2-carbaldehyde 
• 212184-60-6 (2,5-Dimethoxy-benzyl)-(2-phenylsulfanyl-ethyl)-amine 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 212184-69-5 2-formyl-1,2,3,4-tetrahydro-5,8-dimethoxyisoquinoline 

Relevant articles and documents

A synthesis of mono- and dimethoxy-1,2,3,4-tetrahydroisoquinolines via Pummerer reaction: Effects of methoxyl groups on intramolecular cyclization

A synthesis of 1,2,3,4-tetrahydroisoquinolines (TIQs) (23) with one and two methoxyl groups at various positions of the benzene ring was achieved via the intramolecular cyclization of N-(aryl)methyl-2- (phenylsulfinyl)ethylamines (9) using the Pummerer reaction as a key step. The reaction was carried out by using trifluoroacetic anhydride (TFAA) (method A) or TFAA-BF3 · Et2O (method B). The cyclization to 4-SPhTIQs (11) proceeded effectively when the reaction center at the benzene ring was electronically activated by a methoxyl group. In the reaction of the sulfoxide (9e) having two OMe groups at ortho- and para-positions a different cyclization reaction leading to a benzothiazepine (12) was observed, indicating that the high nucleophilicity of the benzene ring caused the unexpected reaction prior to the cyclization to 4-SPhTIQ (11e). The route starting from methoxylated benzaldehydes (5) was proved to provide an efficient and convenient method of TIQ synthesis which should be complementary to the well known Pictet-Spengler method.