65189-15-3

Basic information

• Product Name: 5,6-dichloronicotinonitrile
• Synonyms: 5,6-dichloronicotinonitrile;5-10g;5,6-dichloropyridine-3-carbonitrile
• CAS NO: 65189-15-3
• Molecular Formula: C₆H₂Cl₂N₂
• Molecular Weight: 173
• Mol File: 65189-15-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 146-148°
• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 5,6-dichloronicotinonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-dichloronicotinonitrile(65189-15-3)
• EPA Substance Registry System: 5,6-dichloronicotinonitrile(65189-15-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 65189-15-3(Hazardous Substances Data)

Usage

General Description

5,6-dichloronicotinonitrile is an organic compound with the chemical formula C6H2Cl2N2. It is a derivative of nicotinonitrile, which is used in the synthesis of various pharmaceuticals and agrochemicals. 5,6-dichloronicotinonitrile is a white to light brown solid that is slightly soluble in water but highly soluble in organic solvents. It is primarily used as an intermediate in the production of insecticides, herbicides, and fungicides. Additionally, it is also utilized in the synthesis of various other organic compounds and has potential applications in medicinal chemistry. However, it is important to handle 5,6-dichloronicotinonitrile with caution as it is a hazardous chemical with potential health and environmental risks if not used and disposed of properly.

Synthetic route

5,6-dichloro-nicotinamide (75291-84-8) → 5,6-dichloro-3-pyridinecarbonitrile (65189-15-3)

Conditions	Yield
With thionyl chloride In neat (no solvent) for 72h; Reflux;	78%

2-amino-3-chloro-5-cyanopyridine → 5,6-dichloro-3-pyridinecarbonitrile (65189-15-3)

Conditions	Yield
With tert.-butylnitrite; copper dichloride In acetonitrile at 65℃; for 4h;	63%

diazotized 5,6-dichloro-<3>pyridylamine → 5,6-dichloro-3-pyridinecarbonitrile (65189-15-3)

Conditions	Yield
With potassium cyanide; water; copper(II) sulfate

C6H6Cl2N2 (1256794-26-9) → 5,6-dichloro-3-pyridinecarbonitrile (65189-15-3)

Conditions	Yield
With thionyl chloride Heating / reflux;

oxalyl dichloride (79-37-8) + 5,6-dichloronicotinic acid (41667-95-2) → 5,6-dichloro-3-pyridinecarbonitrile (65189-15-3)

Conditions	Yield
With thionyl chloride; ammonia In tetrahydrofuran; N-methyl-acetamide; methanol; dichloromethane	268 mg (27%)

5,6-dichloronicotinic acid (41667-95-2) → 5,6-dichloro-3-pyridinecarbonitrile (65189-15-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: thionyl chloride; N,N-dimethyl-formamide / tetrahydrofuran / 2.5 h / 50 °C 1.2: 0 - 20 °C 2.1: thionyl chloride / neat (no solvent) / 72 h / Reflux View Scheme

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → tert-butyl 4-(3-chloro-5-cyanopyridin-2-yl)piperazine-1-carboxylate (898227-44-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 120℃; for 18h;	100%

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) + L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → methyl (2S,4R)-1-(3-chloro-5-cyanopyridin-2-yl)-4-hydroxypyrrolidine-2-carboxylate (1243560-55-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 120℃; for 0.333333h; Irradiation with microwave;	98%

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) + 4-tert-Butylaniline (769-92-6) → C16H16ClN3

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 120℃; Inert atmosphere;	93%

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) + ethanolamine (141-43-5) → 5-chloro-6-[(2-hydroxyethyl)amino]nicotinonitrile (1243559-78-5)

Conditions	Yield
In 1,4-dioxane at 80℃; for 24h;	89%

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) → 5,6-Dichloro-N-hydroxy-3-pyridinecarboximidamide

Conditions	Yield
With hydroxylamine hydrochloride; sodium methylate In methanol	82%

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) + (S)(+)-2-ethylpiperazine (207284-20-6) → C12H15ClN4 (906815-77-8)

Conditions	Yield
With caesium carbonate; palladium diacetate; johnphos In 1,4-dioxane at 80℃; for 48h;	75%

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) + 2-methoxyethylamine (109-85-3) → 5-chloro-6-[(2-methoxyethyl)amino]nicotinonitrile (1243559-55-8)

Conditions	Yield
With triethylamine In 1,4-dioxane at 20℃; for 24h;	75%

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) + tert-butyl 3-aminopropanoate (15231-41-1) → tert-butyl 3-[(3-chloro-5-cyanopyridin-2-yl)amino]propanoate (1243559-58-1)

Conditions	Yield
With triethylamine at 20℃; for 24h;	72%

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) + 4-chloro-aniline (106-47-8) → 5-chloro-6-(4-chlorophenylamino)nicotinonitrile (951771-53-2)

Conditions	Yield
Stage #1: 5,6-dichloro-3-pyridinecarbonitrile; 4-chloro-aniline; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 20℃; for 0.333333h; Stage #2: With potassium carbonate In toluene at 100℃; for 16h;	71%
With palladium diacetate; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 16h; Buchwald reaction;	71%

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) + sodium thiomethoxide (5188-07-8) → 5-chloro-2-methylthio-3-pyridinecarbonitrile

Conditions	Yield
In hexane; dimethyl sulfoxide; ethyl acetate	71%

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) + {1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert.-butyl ester (1032528-06-5) → tert-butyl 1-(4-(3-chloro-5-cyanopyridin-2-yl)phenyl)cyclobutylcarbamate (1357159-01-3)

Conditions	Yield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate In water; acetonitrile at 80℃; for 18h; Suzuki coupling; Inert atmosphere;	70%

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) → 5,6-dichloronicotinic acid (41667-95-2)

Conditions	Yield
With hydrogenchloride; diethyl ether

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) → 5-chloro-6-mercapto-nicotinic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous methanol; KHS 2: aqueous HCl / 120 °C View Scheme

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) → 5,6-dichloro-N'-hydroxynicotinimidamide (261625-31-4)

Conditions	Yield
With hydroxylamine	234 mg (76%)

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) + 3-tert-butyl-2-phenyl-5-hydroxymethyloxazolidine (30315-49-2) → S-2-(tert. butylamino-2-hydroxypropoxy)-3-chloro-5-cyanopyridine

Conditions	Yield
With hydrogenchloride; sodium hydroxide In water; toluene; mineral oil; Petroleum ether
With hydrogenchloride; sodium hydroxide In water; toluene; mineral oil; Petroleum ether
With hydrogenchloride; sodium hydroxide In water; toluene; mineral oil; Petroleum ether
With hydrogenchloride; sodium hydroxide In water; toluene; mineral oil; Petroleum ether

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) + Glycine tert-butyl ester (6456-74-2) → tert-butyl [(3-chloro-5-cyanopyridin-2-yl)amino]acetate (1243559-61-6)

Conditions	Yield
With triethylamine at 20℃; for 24h;

(1R,2S)-2-amino-cyclopentanecarboxylic acid methyl ester (154460-33-0) + 5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) → cis-methyl 2-(3-chloro-5-cyanopyridin-2-ylamino)cyclopentanecarboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile for 24h; Heating; Reflux;

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) + tert-butyl 4-aminobutanoate hydrochloride → tert-butyl 4-[(3-chloro-5-cyanopyridin-2-yl)amino]butanoate (1243559-71-8)

Conditions	Yield
With sodium hydrogencarbonate at 50℃; for 16h; Inert atmosphere of nitrogen;

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) → 5-chloro-6-(4-chlorophenylamino)nicotinamidine (951771-70-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: palladium diacetate; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 16 h / 100 °C 2.1: sodium methylate / methanol / 16 h / 20 °C 2.2: 2 h / 65 °C View Scheme

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) → 3-chloro-N-(4-chlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)pyridin-2-amine

Conditions	Yield
Multi-step reaction with 3 steps 1.1: palladium diacetate; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 16 h / 100 °C 2.1: sodium methylate / methanol / 16 h / 20 °C 2.2: 2 h / 65 °C 3.1: potassium hydrogencarbonate / tetrahydrofuran; water / 5 h / 80 °C View Scheme

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) → 3-chloro-N-(4-chlorophenyl)-5-(1,5-dimethyl-1H-imidazol-2-yl)pyridin-2-amine + 3-chloro-N-(4-chlorophenyl)-5-(1,4-dimethyl-1H-imidazol-2-yl)pyridin-2-amine

Conditions	Yield
Multi-step reaction with 4 steps 1.1: palladium diacetate; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 16 h / 100 °C 2.1: sodium methylate / methanol / 16 h / 20 °C 2.2: 2 h / 65 °C 3.1: potassium hydrogencarbonate / tetrahydrofuran; water / 5 h / 80 °C 4.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C View Scheme

5,6-dichloro-3-pyridinecarbonitrile (65189-15-3) → 3-chloro-N-(4-chlorophenyl)-5-(4-methyl-1-propyl-1H-imidazol-2-yl)pyridin-2-amine

Conditions	Yield
Multi-step reaction with 4 steps 1.1: palladium diacetate; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 16 h / 100 °C 2.1: sodium methylate / methanol / 16 h / 20 °C 2.2: 2 h / 65 °C 3.1: potassium hydrogencarbonate / tetrahydrofuran; water / 5 h / 80 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 20 °C 4.2: 0.5 h / 20 °C View Scheme

Upstream product

• 156361-02-3 2-amino-3-chloro-5-cyanopyridine 
• 1256794-26-9 C₆H₆Cl₂N₂ 
• 79-37-8 oxalyl dichloride 
• 41667-95-2 5,6-dichloronicotinic acid 
• 75291-84-8 5,6-dichloro-nicotinamide 

Downstream Products

• 951771-53-2 5-chloro-6-(4-chlorophenylamino)nicotinonitrile 
• 1243560-55-5 methyl (2S,4R)-1-(3-chloro-5-cyanopyridin-2-yl)-4-hydroxypyrrolidine-2-carboxylate 
• 951771-70-3 5-chloro-6-(4-chlorophenylamino)nicotinamidine 
• 1357158-81-6 6-(4-(1-aminocyclobutyl)phenyl)-5-phenylnicotinamide 
• 1357159-01-3 tert-butyl 1-(4-(3-chloro-5-cyanopyridin-2-yl)phenyl)cyclobutylcarbamate 
• 1243560-59-9 methyl (2S,4R)-1-(3-chloro-5-(5-(2-(methoxymethyl)-2'-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)-4-hydroxypyrrolidine-2-carboxylate 
• 1243560-58-8 methyl (2S,4R)-1-(3-chloro-5-(5-(2-(methoxymethyl)-2'-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)-4-(tert-butyldimethylsilyloxy)-pyrrolidine-2-carboxylate 

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