73075-59-9

Basic information

• Product Name: 5,8-DICHLOROISOQUINOLINE
• Synonyms: 5,8-DICHLOROISOQUINOLINE
• CAS NO: 73075-59-9
• Molecular Formula: C9H5Cl2N
• Molecular Weight: 198.05
• Mol File: 73075-59-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 116-118 °C
• Boiling Point: 321.4°C at 760 mmHg
• Flash Point: 177.8°C
• Appearance: /
• Density: 1.407g/cm³
• Vapor Pressure: 0.00056mmHg at 25°C
• Refractive Index: 1.66
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.65±0.36(Predicted)
• CAS DataBase Reference: 5,8-DICHLOROISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,8-DICHLOROISOQUINOLINE(73075-59-9)
• EPA Substance Registry System: 5,8-DICHLOROISOQUINOLINE(73075-59-9)

Safety Data

• Hazardous Substances Data: 73075-59-9(Hazardous Substances Data)

Usage

General Description

5,8-Dichloroisoquinoline is a chemical compound with the molecular formula C9H5Cl2N. It is a heterocyclic compound that consists of a fused isoquinoline and a chlorine atom at positions 5 and 8. 5,8-DICHLOROISOQUINOLINE is commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals due to its versatile reactivity and ability to form various functional groups. It is also employed as a precursor in the preparation of organic compounds such as dyes, pigments, and fluorescent materials. Additionally, 5,8-Dichloroisoquinoline has potential applications in medicinal chemistry as it exhibits biological activities, and its derivatives have been investigated for their antimalarial, antiviral, and anticancer properties. Despite its utility, this compound should be handled with caution as it may pose health and environmental hazards.

InChI:InChI=1/C9H5Cl2N/c10-8-1-2-9(11)7-5-12-4-3-6(7)8/h1-5H

Upstream product

• 6361-23-5 2,5-dichloro-benzaldehyde 
• 119-65-3 isoquinoline 
• 118-52-5 1,3-dichloro-5,5-dimethylhydantoin 
• 22483-09-6 2,2-dimethoxyethylamine 
• 34145-05-6 2,5-dichlorobenzyl alcohol 

Downstream Products

• 89315-57-1 5,8-Dichloro-1,2,3,4-tetrahydro-isoquinoline 
• 1198775-29-9 7-nitro-5,8-dichloroisoquinoline 
• 24464-39-9 6-phenyl-1,2,3,4-tetrahydro-isoquinoline 
• 109855-79-0 7-(2-azidophenyl)-5,8-dimethylisoquinoline 
• 519-23-3 ellipticine 
• 109855-80-3 5,6a-dimethyl-6aH-pyrido[3,4-a]carbazole 

Relevant articles and documents

Regioexhaustive Functionalization of the Carbocyclic Core of Isoquinoline: Concise Synthesis of Oxoaporphine Core and Ellipticine

A general and versatile strategy has been developed for the functionalization of the carbocyclic core of the isoquinoline. This regioexhaustive approach employs electrophilic halogenation as a toolbox methodology and delivers highly decorated intermediates that can be further elaborated toward medicinally relevant building blocks or natural products.

Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis: I. Chloro-substituted 1,2,3,4-tetrahydroisoquinolines

In a search for inhibitors of epinephrine biosynthesis as potential therapeutic agents, a series of 13 ring-chlorinated 1,2,3,4-tetrahydroisoquinolines was prepared. These compounds were tested initially for their ability to inhibit rabbit adrenal phenylethanolamine N-methyltransferase (PNMT) in vitro. Enzyme-inhibitor dissociation constants, determined for the six most potent members of the series, indicated the following order of decreasing potency: 7,8-Cl2>6,7,8-Cl3>7-Cl~8-Cl>5,6,7,8-Cl4>5,7,8-Cl3. These compounds were subsequently examined for PNMT-inhibiting activity in intact rats and mice. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline (SK&F 64139) was the most potent member of the series both in vitro and in vivo and is currently undergoing clinical investigation.