82771-60-6

Basic information

• Product Name: 7-CHLORO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE
• Synonyms: 7-CHLORO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE;C90104;7-Chloro-1,2,3,4-tetrahydro-isoquinoline 1HCl salt;Isoquinoline,7-chloro-1,2,3,4-tetrahydro-
• CAS NO: 82771-60-6
• Molecular Formula: C₉H₁₀ClN
• Molecular Weight: 167.64
• EINECS: -0
• Mol File: 82771-60-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 214-217 °C(Solv: ethanol (64-17-5))
• Boiling Point: 267.686 °C at 760 mmHg
• Flash Point: 115.693 °C
• Appearance: /Solid
• Density: 1.162 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 9.15±0.20(Predicted)
• CAS DataBase Reference: 7-CHLORO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-CHLORO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE(82771-60-6)
• EPA Substance Registry System: 7-CHLORO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE(82771-60-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 82771-60-6(Hazardous Substances Data)

Usage

General Description

7-Chloro-1,2,3,4-tetrahydro-isoquinoline is a chemical compound with two aromatic rings and one chlorine substitution. The chemical falls under the category of tetrahydroisoquinolines, a class of compounds that appear in various pharmaceuticals. This chemical tends to be pale yellow in color, exhibits a molecular weight of 187.68 g/mol, and yields the molecular formula C9H10ClN. Although its toxicity and environmental impacts have not been thoroughly explored, it should be handled with care given its potential reactivity. It's commonly utilized in research and in the manufacture of specific types of synthetic chemicals.

Upstream product

• 34784-06-0 7-chloroisoquinoline 
• 111875-09-3 3-(7-Chloro-3,4-dihydro-1H-isoquinoline-2-sulfonyl)-propionic acid methyl ester 
• 78104-41-3 2-acetyl-7-chloro-1,2,3,4-tetrahydroisoquinoline 
• 88422-94-0 N-<2-(4-chlorophenyl)ethyl>acetamide 
• 156-41-2 4-chlorophenylethylamine 
• 140-53-4 p-chlorobenzyl cyanide 
• 111874-99-8 3-[2-(4-Chloro-phenyl)-ethylsulfamoyl]-propionic acid methyl ester 
• 1004522-39-7 C₉H₁₂ClNO 
• 64834-58-8 2-((2-chlorobenzyl)amino)ethan-1-ol 
• 89-98-5 2-chloro-benzaldehyde 
• 71006-02-5 2-(2-chloro-benzylideneamino)-ethanol 
• 22245-95-0 7-chloro-1,2,3,4-tetrahydroisoquinolin-1-one 

Downstream Products

• 60518-41-4 7-chloro-3,4-dihydroisoquinoline 
• 73075-45-3 7-chloro-1,2,3,4-tetrahydroisoquinoline hydrochloride 

Relevant articles and documents

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Metal-Free Synthesis of Polycyclic Quinazolinones Enabled by a (NH4)2S2O8-Promoted Intramolecular Oxidative Cyclization

An efficient metal-free, (NH4)2S2O8 mediated intramolecular oxidative cyclization for the construction of polycyclic heterocycles was disclosed. A series of polycyclic quinazolinone derivatives with good functional group tolerance were obtained in high yields. The natural products tryptanthrin and rutaecarpine, as well as their derivatives, were easily synthesized by this strategy. A preliminary mechanism study suggested the carbon-centered radical was involved in the catalytic cycle.

Synthesis and further transformations of 8-chloro-3,4-dihydroisoquinoline

Two procedures for the synthesis of barely accessible 8-chloro-3,4-dihydroisoquinoline were investigated. The first approach is based on a directed ortho-lithiation of N-pivaloyl meta-chlorophenylethylamine, followed by formylation and subsequent ring closure under acidic conditions. In the second, more advantageous variant, the N-hydroxyethyl ortho-chlorobenzylamine intermediate undergoes a Friedel-Crafts reaction, and the resulting tetrahydro derivative is oxidized with N-bromosuccinimide. The 8-chloro-3,4-dihydroisoquinoline key intermediate is then applied in Suzuki reactions to give various 8-aryl-3,4-dihydroisoquinolines, which are finally treated with alkyl or aryllithiums to give 1-substituted 8-aryl-1,2,3,4-tetrahydroisoquinolines. These novel 1,2,3,4-tetrahydroisoquinoline derivatives can be used as building blocks in the synthesis of potential drug candidates.