444588-09-4

Basic information

• Product Name: 2-benzyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
• Synonyms: 2-benzyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 444588-09-4
• Molecular Weight: 268.315
• Mol File: 444588-09-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-benzyl-7-nitro-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-benzyl-7-nitro-1,2,3,4-tetrahydroisoquinoline(444588-09-4)
• EPA Substance Registry System: 2-benzyl-7-nitro-1,2,3,4-tetrahydroisoquinoline(444588-09-4)

Safety Data

• Hazardous Substances Data: 444588-09-4(Hazardous Substances Data)

Upstream product

• 42923-79-5 7-nitro-1,2,3,4-tetrahydroisoquinoline 
• 100-39-0 benzyl bromide 
• 100-46-9 benzylamine 
• 108130-11-6 1-(2-chloro-ethyl)-2-chloromethyl-4-nitro-benzene 
• 13605-95-3 N-benzyl-1,2,3,4-tetrahydroisoquinoline 
• 15787-39-0 2-benzylisoquinolin-2-ium iodide 

Relevant articles and documents

Gold Catalyzed Photoredox C1-Alkynylation of N-Alkyl-1,2,3,4- tetrahydroisoquinolines by 1-Bromoalkynes with UVA LED Light

A synthetic method that combines [Au2(m-dppm)2]Cl2 (dppm=bis(diphenylphosphanyl)methane) and UVA LED (LED=light emitting diode) light (365 nm) to catalyze the regioselective C1-alkynylation of N-alkyl-1,2,3,4-tetrahydroisoquinolines (THIQs) with alkynyl bromides is described. The reaction mechanism was delineated to involve a reductive quench pathway to generate the two posited radical species of the nitrogen-containing heterocycle and organic halide. In contrast, radical formation via an oxidative quench pathway was suggested to be operative in analogous control experiments with a 1-iodoalkyne. The usefulness of this carbon-carbon bond forming strategy was also exemplified by its application to the formal synthesis of the opioid analgesic drug methopholine and synthesis of a protoberberine alkaloid derivative.