70810-24-1

Basic information

• Product Name: 1,7-Dichloroisoquinoline
• Synonyms: 1,7-Dichloroisoquinoline;N-cyclohexyl-1-phenyl-1H-pyrazolo[3,4-d]pyriMidin-4-aMine
• CAS NO: 70810-24-1
• Molecular Formula: C₉H₅Cl₂N
• Molecular Weight: 198.051
• Mol File: 70810-24-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 138 °C
• Boiling Point: 316 °C at 760 mmHg
• Flash Point: 174.2 °C
• Appearance: /
• Density: 1.407
• Vapor Pressure: 0.000782mmHg at 25°C
• Refractive Index: 1.66
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.30±0.33(Predicted)
• CAS DataBase Reference: 1,7-Dichloroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 1,7-Dichloroisoquinoline(70810-24-1)
• EPA Substance Registry System: 1,7-Dichloroisoquinoline(70810-24-1)

Safety Data

• Hazardous Substances Data: 70810-24-1(Hazardous Substances Data)

Usage

General Description

1,7-Dichloroisoquinoline is a chemical compound with the molecular formula C9H5Cl2N. It is a pale yellow crystalline solid that is primarily used in organic synthesis and as a building block for pharmaceuticals and agrochemicals. 1,7-Dichloroisoquinoline has been shown to exhibit antifungal and antibacterial properties, making it a useful ingredient in the development of new drugs. It is also utilized in the production of dyes, herbicides, and insecticides. The compound is highly stable and can be stored and transported safely under recommended conditions. Due to its diverse range of applications, 1,7-Dichloroisoquinoline is considered an important intermediate in the chemical industry.

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

Synthetic route

7-chloro-isoquinoline-2-oxide-hydrochloride → 1,7-dichloroisoquinoline (70810-24-1)

Conditions	Yield
With trichlorophosphate

isoquinoline-1,7-diol (59647-24-4) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) → 1,7-dichloroisoquinoline (70810-24-1)

Conditions	Yield
at 165℃;

7-chloroisoquinoline 2-oxide (70810-26-3) → 1,7-dichloroisoquinoline (70810-24-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: p-toluenesulfonyl chloride / N,N-dimethyl-formamide / 80 °C 2: thionyl chloride; N,N-dimethyl-formamide / toluene / 3 h / 80 °C View Scheme

7-chloroisoquinolin-1-ol (24188-74-7) → 1,7-dichloroisoquinoline (70810-24-1)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide In toluene at 80℃; for 3h;
With thionyl chloride; N,N-dimethyl-formamide In toluene at 80℃; for 3h;

1,7-dichloroisoquinoline (70810-24-1) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → tert-butyl 4-(7-chloroisoquinolin-1-yl)piperazine-1-carboxylate

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 110℃; for 5h; Inert atmosphere;	93%
With potassium carbonate In dimethyl sulfoxide at 120℃; for 5.5h;	73%

1,7-dichloroisoquinoline (70810-24-1) + 4-aminobenzene sulfonic acid (121-57-3) → 4-(7-chloroisoquinolin-1-ylamino)benzenesulfonic acid

Conditions	Yield
In ethanol; water at 80℃;	84%

1,7-dichloroisoquinoline (70810-24-1) + methyl 5-amino-2-pyridinecarboxylate (67515-76-8) → methyl 5-((7-chloroisoquinolin-1-yl)amino)picolinate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 130 - 140℃;	76%

1,7-dichloroisoquinoline (70810-24-1) + 1-phenylmethylpiperazine (2759-28-6) → 1-(4-benzylpiperazin-1-yl)-7-chloroisoquinoline

Conditions	Yield
at 150℃; for 3h;	71%
at 150℃; for 3h;	71%

1,7-dichloroisoquinoline (70810-24-1) + N-(3-aminophenylsulfonyl)benzylamine (303780-52-1) → N-benzyl-3-((7-chloroisoquinolin-1-yl)amino)benzenesulfonamide

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 130℃;	61%

1,7-dichloroisoquinoline (70810-24-1) + 6-chloro-N-methylpyridazin-3-amine (14959-32-1) → 7-chloro-N-(6-chloropyridazin-3-yl)-N-methylisoquinolin-1-amine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 130℃; Inert atmosphere;	53%

potassium cyanide + 1,7-dichloroisoquinoline (70810-24-1) → 7-chloroisoquinoline-1-carbonitrile (1368066-86-7)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; 1,5-bis-(diphenylphosphino)pentane; palladium diacetate In toluene at 150℃; Inert atmosphere;	25%

1,7-dichloroisoquinoline (70810-24-1) + C9H14N4O2 → tert-butyl (2-((7-chloroisoquinolin-1-yl)amino)pyrimidin-4-yl)carbamate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 140℃; Inert atmosphere;	16%

1,7-dichloroisoquinoline (70810-24-1) + diethylaminopropylamine (104-78-9) → N,N-diethyl-N'-(7-chloro-[1]isoquinolyl)-propanediyldiamine

Conditions	Yield
at 150 - 200℃;

piperazine (110-85-0) + 1,7-dichloroisoquinoline (70810-24-1) → 7-chloro-1-(piperazin-1-yl)isoquinoline

Conditions	Yield
In ethylene glycol at 140℃;

1,7-dichloroisoquinoline (70810-24-1) → (2S,2'S)-N,N'-(4,4'-((E)-ethene-1,2-diyl)bis(4,1-phenylene))bis(1-(7-chloroisoquinoline-1-carbonyl)pyrrolidine-2-carboxamide) (1429787-76-7)

Conditions

Yield

Multi-step reaction with 3 steps 1.1: 1,5-bis-(diphenylphosphino)pentane; N,N,N,N,-tetramethylethylenediamine; palladium diacetate / toluene / 150 °C / Inert atmosphere 2.1: sodium hydroxide / 80 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere View Scheme

1,7-dichloroisoquinoline (70810-24-1) → 7-chloroisoquinoline-1-carboxylic acid (552850-71-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1,5-bis-(diphenylphosphino)pentane; N,N,N,N,-tetramethylethylenediamine; palladium diacetate / toluene / 150 °C / Inert atmosphere 2.1: sodium hydroxide / 80 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere View Scheme

1,7-dichloroisoquinoline (70810-24-1) → N3-(7-chloroisoquinolin-1-yl)-3-N-methylpyridazine-3,6-diamine

Conditions

Yield

Multi-step reaction with 3 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 130 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / 1,4-dioxane / 100 °C 3: trifluoroacetic acid / 60 °C View Scheme

1,7-dichloroisoquinoline (70810-24-1) → 3-N-(7-chloroisoquinolin-1-yl)-6-N-(4-methoxybenzyl)-3-N-methylpyridazine-3,6-diamine

Conditions	Yield
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 130 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / 1,4-dioxane / 100 °C View Scheme

1,7-dichloroisoquinoline (70810-24-1) + tert-butyl (4-aminopyridin-2-yl)carbamate → tert-butyl (4-((7-chloroisoquinolin-1-yl)amino)pyridin-2-yl)carbamate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 140℃; Inert atmosphere;

1,7-dichloroisoquinoline (70810-24-1) + tert-butyl (4-aminopyridin-2-yl)carbamate → N4-(7-chloroisoquinolin-1-yl)pyridine-2,4-diamine

Conditions	Yield
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 140 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 20 °C View Scheme

1,7-dichloroisoquinoline (70810-24-1) → 7-chloro-1-(piperazin-1-yl)isoquinoline

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / dimethyl sulfoxide / 5.5 h / 120 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / dimethyl sulfoxide / 5 h / 110 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C View Scheme

1,7-dichloroisoquinoline (70810-24-1) → tert-butyl N-{3-[4-(7-chloroisoquinolin-1-yl)piperazin-1-yl]propyl}carbamate

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / dimethyl sulfoxide / 5.5 h / 120 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 20 °C View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / dimethyl sulfoxide / 5 h / 110 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 20 °C View Scheme

1,7-dichloroisoquinoline (70810-24-1) → 3-[4-(7-chloroisoquinolin-1-yl)piperazin-1-yl]propan-1-amine

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate / dimethyl sulfoxide / 5.5 h / 120 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 20 °C 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: potassium carbonate / dimethyl sulfoxide / 5 h / 110 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 20 °C 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C View Scheme

1,7-dichloroisoquinoline (70810-24-1) → 4-({3-[4-(7-chloroisoquinolin-1-yl)piperazin-1-yl]propyl}amino)-2H-chromen-2-one

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium carbonate / dimethyl sulfoxide / 5.5 h / 120 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 20 °C 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5: triethylamine / acetonitrile / 1 h / 70 °C View Scheme
Multi-step reaction with 5 steps 1: potassium carbonate / dimethyl sulfoxide / 5 h / 110 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 20 °C 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5: triethylamine / acetonitrile / 1 h / 70 °C View Scheme

1,7-dichloroisoquinoline (70810-24-1) → 4-({3-[4-(7-chloroisoquinolin-1-yl)piperazin-1-yl]propyl}amino)-2H-chromen-2-one hydrochloride

Conditions	Yield
Multi-step reaction with 6 steps 1: potassium carbonate / dimethyl sulfoxide / 5.5 h / 120 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 20 °C 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5: triethylamine / acetonitrile / 1 h / 70 °C 6: hydrogenchloride / dichloromethane; diethyl ether View Scheme
Multi-step reaction with 6 steps 1: potassium carbonate / dimethyl sulfoxide / 5 h / 110 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 20 °C 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5: triethylamine / acetonitrile / 1 h / 70 °C 6: hydrogenchloride / dichloromethane; methanol; diethyl ether View Scheme

1,7-dichloroisoquinoline (70810-24-1) → 4-((7-chloroisoquinolin-1-yl)amino)benzenesulfonyl chloride

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol; water / 80 °C 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C View Scheme

1,7-dichloroisoquinoline (70810-24-1) → 4-((7-chloroisoquinolin-1-yl)amino)-N-(1,2,3,4-tetrahydronaphthalen-2-yl)benzenesulfonamide

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol; water / 80 °C 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 3: triethylamine / dichloromethane / 0 - 20 °C View Scheme

1,7-dichloroisoquinoline (70810-24-1) → 4-((7-chloroisoquinolin-1-yl)amino)-N-((1,2,3,4-tetrahydronaphthalen-2-yl)methyl)benzenesulfonamide

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol; water / 80 °C 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C View Scheme

1,7-dichloroisoquinoline (70810-24-1) → N-benzyl-4-((7-chloroisoquinolin-1-yl)amino)benzenesulfonamide

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol; water / 80 °C 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 3: pyridine / 3 h / 20 °C View Scheme

Upstream product

• 24188-74-7 7-chloroisoquinolin-1-ol 
• 70810-26-3 7-chloroisoquinoline 2-oxide 
• 59647-24-4 isoquinoline-1,7-diol 
• 10025-87-3 trichlorophosphate 

Downstream Products

• 552850-71-2 7-chloroisoquinoline-1-carboxylic acid 

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