226942-29-6

Basic information

• Product Name: 6-bromo-1,2,3,4-tetrahydroisoquinoline
• Synonyms: Isoquinoline,6-broMo-1,2,3,4-tetrahydro-;6-Bromo-1,2,3,4-tetrahydroisoquinoline HCl
• CAS NO: 226942-29-6
• Molecular Formula: C₉H₁₀BrN
• Molecular Weight: 212.09
• EINECS: -0
• Mol File: 226942-29-6.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 283℃
• Flash Point: 125℃
• Appearance: /Solid
• Density: 1.428
• Vapor Pressure: 0.00326mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 9.26±0.20(Predicted)
• CAS DataBase Reference: 6-bromo-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromo-1,2,3,4-tetrahydroisoquinoline(226942-29-6)
• EPA Substance Registry System: 6-bromo-1,2,3,4-tetrahydroisoquinoline(226942-29-6)

Safety Data

• Hazardous Substances Data: 226942-29-6(Hazardous Substances Data)

Usage

Description

6-bromo-1,2,3,4-tetrahydroisoquinoline is a chemical compound with the molecular formula C9H10BrN. It is a derivative of tetrahydroisoquinoline, a class of organic compounds found in various plants and natural products. The bromine atom at the 6-position of the tetrahydroisoquinoline ring endows this compound with unique properties and reactivity. This chemical has potential applications in medicinal chemistry and pharmaceutical research due to its ability to mimic the structure and activity of naturally occurring alkaloids. It is also used as a building block for the synthesis of various bioactive compounds.

Uses

Used in Medicinal Chemistry:
6-bromo-1,2,3,4-tetrahydroisoquinoline is used as a structural mimic for naturally occurring alkaloids, which is beneficial for the development of new pharmaceutical agents. Its unique reactivity and properties allow it to be a promising candidate in the design and synthesis of novel bioactive compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 6-bromo-1,2,3,4-tetrahydroisoquinoline is used as a building block for the synthesis of various bioactive compounds. Its ability to mimic the structure and activity of alkaloids makes it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
6-bromo-1,2,3,4-tetrahydroisoquinoline is used as a key intermediate in the synthesis of a wide range of chemical compounds. Its unique reactivity and properties make it a versatile building block for creating new molecules with potential applications in various fields.

InChI:InChI=1/C9H10BrN/c10-9-2-1-8-6-11-4-3-7(8)5-9/h1-2,5,11H,3-4,6H2

Upstream product

• 252331-63-8 1-(6-bromo-3,4-dihydro-1H-isoquinolin-2-yl)-2,2,2-trifluoro-ethanone 
• 726136-49-8 1-(8-bromo-3,4-dihydro-1H-isoquinolin-2-yl)-2,2,2,-trifluoro-ethanone 
• 147497-32-3 6-bromo-3,4-dihydroisoquinolin-1(2H)-one 
• 58971-11-2 2-(3-bromophenyl)ethanamine 
• 34784-05-9 6-bromo-isoquinoline 

Downstream Products

• 893566-75-1 tert-butyl 8-bromo-1,2,3,4-tetrahydroisoquinoline-2-carboxylate 
• 893566-74-0 6-bromo-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline 
• 1296865-65-0 2-[3-(1-benzyl-1H-tetrazol-5-ylthio)propyl]-6-bromo-1,2,3,4-tetrahydroisoquinoline 
• 922718-57-8 2-methyl-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline 
• 1181690-16-3 (R)-2-hydroxy-1-(6-(4-(2-(2-methylpyrrolidin-1-yl)ethyl)phenyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone hydrochloride 

Relevant articles and documents

Intramolecular Reductive Cyclization of o-Nitroarenes via Biradical Recombination

A visible-light-induced/thiourea-mediated intramolecular cyclization of o-nitroarenes under mild conditions is realized for the first time, which provides an efficient and environmentally friendly way to access pharmaceutical relevant quinazolinone derivatives. The reaction can be easily extended to gram level by using a continuous-flow setup with high efficiency. Mechanistic investigation including control experiments, transient fluorescence, UV-vis spectra, and DFT calculations suggests that the formation of active biradical intermediates via intramolecular single electron transfer (SET) is key stage in the catalytic cycle.

Light-Driven Intramolecular C?N Cross-Coupling via a Long-Lived Photoactive Photoisomer Complex

Reported herein is a visible-light-driven intramolecular C?N cross-coupling reaction under mild reaction conditions (metal- and photocatalyst-free, at room temperature) via a long-lived photoactive photoisomer complex. This strategy was used to rapidly prepare the N-substituted polycyclic quinazolinone derivatives with a broad substrate scope (>50 examples) and further exploited to synthesize the natural products tryptanthrin, rutaecarpine, and their analogues. The success of gram-scale synthesis and solar-driven transformation, as well as promising tumor-suppressing biological activity, proves the potential of this strategy for practical applications. Mechanistic investigations, including control experiments, DFT calculations, UV-vis spectroscopy, EPR, and X-ray single-crystal structure of the key intermediate, provides insight into the mechanism.

Highly active and recyclable Pt nanocatalyst for hydrogenation of quinolines and isoquinolines

Thermoregulated phase-transfer Pt nanocatalyst was shown to be highly active, selective and recyclable in the hydrogenation of quinolines and isoquinolines. The catalyst could be easily separated from the product by simple phase separation and directly reused in the next cycle without evident loss in catalytic activity and selectivity, even after ten recycles. Importantly, for quinoline, the TON of 10,474 is the highest value ever reported among Pt catalysts. More remarkably, for isoquinoline, the TON of 5340 is far ahead of the highest record among transition metal catalysts.