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

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

Uses

Used in Pharmaceutical and Agrochemical Industries:
5,8-Dichloroisoquinoline is utilized as a building block in the synthesis of pharmaceuticals and agrochemicals, leveraging its reactivity to create a range of functional groups that contribute to the development of new drugs and pesticides.
Used in Organic Compound Preparation:
5,8-DICHLOROISOQUINOLINE serves as a precursor in the preparation of organic compounds such as dyes, pigments, and fluorescent materials, where its unique structure and reactivity are essential for the desired properties of these products.
Used in Medicinal Chemistry Research:
5,8-Dichloroisoquinoline and its derivatives are under investigation for their potential applications in medicinal chemistry, particularly for their antimalarial, antiviral, and anticancer properties, making it a valuable compound in the search for new therapeutic agents.

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

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.

The development of a new manufacturing route to the novel anticonvulsant, SB-406725A

The development of an efficient manufacturing route to 3-acetyl - N - (5,8-dichloro-1,2,3,4-tetrahydro-7-isoquinolinyl)-4-(1-methyl- ethoxy)-benzamide hydrochloride SB-406725A (1) is described. The synthesis begins with dichlorination of isoquinoline, followed by nitration using nitronium tetrafluoroborate in sulpholane. Nitroisoquinoline (12) was hydrogenated under pressure using Pt/C. The resultant tetrahydroisoquinoline (13) was selectively coupled with benzoate side chain (15) under base-promoted conditions using sodium hexamethyldisilazane to yield the parent molecule SB-406725 (16). SB-406725 was then converted to the HCl salt SB-406725A (1). This process has been successfully demonstrated on a pilot-plant scale to prepare ～30 kg of SB-406725A (1).

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.