6082-66-2

Basic information

• Product Name: 3,4,6-Trichloropyridazine
• Synonyms: 3,4,6-Trichloro-1,2-diazine;3,4,6-TRICHLOROPYRIDAZINE;3-METHYL-2-BENZOXAZOLINONE,PLANT STANDARD;6-Trichloropyridazine
• CAS NO: 6082-66-2
• Molecular Formula: C₄HCl₃N₂
• Molecular Weight: 183.42
• EINECS: 1806241-263-5
• Product Categories: alkyl chloride
• Mol File: 6082-66-2.mol
• Article Data: 23

Chemical Properties

• Melting Point: 55.0 to 59.0 °C
• Boiling Point: 98°C/43mmHg(lit.)
• Flash Point: 173.901 °C
• Appearance: /
• Density: 1.642 g/cm³
• Vapor Pressure: 0.000805mmHg at 25°C
• Refractive Index: 1.578
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: -2.72±0.10(Predicted)
• CAS DataBase Reference: 3,4,6-Trichloropyridazine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,6-Trichloropyridazine(6082-66-2)
• EPA Substance Registry System: 3,4,6-Trichloropyridazine(6082-66-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 6082-66-2(Hazardous Substances Data)

Usage

Uses

3,4,6-Trichloropyridazine was used to study chloropyridazine derivatives as human rhinovirus capsid-binding inhibitors.

InChI:InChI=1/C4HCl3N2/c5-2-1-3(6)8-9-4(2)7/h1H

Synthetic route

4-bromo-1,2-dihydropyridazine-3,6-dione (15456-86-7) → 3,4,6-trichloropyridazine (6082-66-2)

Conditions	Yield
With trichlorophosphate at 110℃; for 5h;	92%
With trichlorophosphate at 100℃; for 3h;	86%
With trichlorophosphate for 4h; Heating;	84%

bromomaleic anhydride (5926-51-2) → 3,4,6-trichloropyridazine (6082-66-2)

Conditions	Yield
Stage #1: bromomaleic anhydride With hydrazine In water for 4h; Reflux; Stage #2: With trichlorophosphate for 3.5h; Reflux;	87%

4-Brom-pyridazin-3,6-diol (15456-86-7) → 3,4,6-trichloropyridazine (6082-66-2)

Conditions	Yield
With trichlorophosphate Reflux;	82%

3,6-dichlorpyridazine (141-30-0) → 3,4,6-trichloropyridazine (6082-66-2)

Conditions	Yield
With chlorine; aluminum (III) chloride at 120℃; for 3h; Neat (no solvent);	55%
With aluminum (III) chloride; chlorine at 140℃; for 4h;
With chlorine; aluminium trichloride
With aluminum (III) chloride; chlorine at 140℃; for 4h;	44.1 g

4-chloro-1,2-dihydro-pyridazine-3,6-dione (5397-64-8) → 3,4,6-trichloropyridazine (6082-66-2)

Conditions	Yield
With trichlorophosphate
With trichlorophosphate; phosphorus trichloride
With trichlorophosphate for 10h; Heating / reflux;
With trichlorophosphate

4-bromo-1,2-dihydropyridazine-3,6-dione (15456-86-7) → 3,4,6-trichloropyridazine (6082-66-2) + 4-bromo-3,6-dichloro-pyridazine (10344-42-0)

Conditions	Yield
With trichlorophosphate for 3.5h; Heating / reflux;

4-bromo-1,2-dihydropyridazine-3,6-dione (15456-86-7) → 3,4,6-trichloropyridazine (6082-66-2) + C4H5BrCl2N2

Conditions	Yield
Stage #1: 4-bromo-1,2-dihydropyridazine-3,6-dione With trichlorophosphate for 3.5h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In water

4-bromo-1,2-dihydropyridazine-3,6-dione (15456-86-7) → 3,4,6-trichloropyridazine (6082-66-2) + C4HBrCl2N2 (1003944-29-3) + 4-bromo-3,6-dichloro-pyridazine (10344-42-0)

Conditions	Yield
With trichlorophosphate for 3.5h; Heating / reflux;

pyridazine-3,4,6-triol (30480-35-4) → 3,4,6-trichloropyridazine (6082-66-2)

Conditions	Yield
With trichlorophosphate at 100℃;

3,4,6-trichloropyridazine (6082-66-2) + Cyclopropylmethanol (2516-33-8) → 3,6-dichloro-4-(cyclopropylmethoxy)pyridazine

Conditions	Yield
Stage #1: Cyclopropylmethanol With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: 3,4,6-trichloropyridazine In tetrahydrofuran at 0 - 20℃; for 1h;	100%

3,4,6-trichloropyridazine (6082-66-2) → 3,6-dichloropyridazin-4-amine (823-58-5)

Conditions	Yield
With ammonia In 1,4-dioxane Reflux;	97%
With ammonium hydroxide In 1,4-dioxane at 90℃; for 12h; regioselective reaction;	86%
With ammonium hydroxide In water at 75℃; for 16h;	76%

3,4,6-trichloropyridazine (6082-66-2) + 4-methoxy-benzylamine (2393-23-9) → 3,6-dichloro-N-[(4-methoxyphenyl)methyl]pyridazin-4-amine

Conditions	Yield
In tetrahydrofuran at 50℃; for 0.5h;	97%
In isopropyl alcohol at 120℃; for 0.666667h; Microwave irradiation; Sealed tube; regioselective reaction;	87%
In tetrahydrofuran at 50℃; for 2h; Sealed tube;	62%
With potassium carbonate In acetonitrile at 95℃; for 4h; Inert atmosphere;

3,4,6-trichloropyridazine (6082-66-2) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → tert-Butyl 4-(3,6-dichloropyridazin-4-yl)piperazine-1-carboxylate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃;	94%

3,4,6-trichloropyridazine (6082-66-2) + sodium methylate (124-41-4) → 3,6-dichloro-4-methoxy-1,2-dihydropyridazine (70952-62-4)

Conditions	Yield
In methanol at 20℃; for 1h;	94%

3,4,6-trichloropyridazine (6082-66-2) + methylamine (74-89-5) → 3,6-dichloro-N-methyl-pyridazin-4-amine (17645-06-6)

Conditions	Yield
In tetrahydrofuran at 50℃; for 2h; Sealed tube;	93.7%
In 1,4-dioxane; water at 20℃; for 0.166667h; regioselective reaction;	88%
In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;

3,4,6-trichloropyridazine (6082-66-2) + dimethyl amine (124-40-3) → 3,6-dichloro-N,N-dimethylpyridazin-4-amine (17258-35-4)

Conditions	Yield
In 1,4-dioxane; water at 0℃; for 0.166667h; regioselective reaction;	93%

3,4,6-trichloropyridazine (6082-66-2) + Cyclopropylamine (765-30-0) → 3,6-dichloro-N-cyclopropylpyridazin-4-amine

Conditions	Yield
In tetrahydrofuran at 50℃; for 3h; Sealed tube;	91.1%
In tetrahydrofuran at 50℃; for 3h;	89%

3,4,6-trichloropyridazine (6082-66-2) + 2-hydroxyethanethiol (60-24-2) → 2-[(3,6-dichloro-4-pyridazinyl)thio]ethanol (943026-17-3)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 72h;	91%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 70.5833h;	91%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 72.0833h;	91%

3,4,6-trichloropyridazine (6082-66-2) + sodium hydrogencarbonate (144-55-8) + 2-hydroxyethanethiol (60-24-2) → 2-[(3,6-dichloro-4-pyridazinyl)thio]ethanol (943026-17-3)

Conditions	Yield
With triethylamine In tetrahydrofuran	91%

3,4,6-trichloropyridazine (6082-66-2) + ethylamine (75-04-7) → 4-ethylamino-3,6-dichloropyridazine (29049-49-8)

Conditions	Yield
With potassium carbonate In tetrahydrofuran; acetonitrile at 0 - 20℃; for 16h; Inert atmosphere;	91%
In water for 2h;

3,4,6-trichloropyridazine (6082-66-2) + benzylamine (100-46-9) → N-benzyl-3,6-dichloropyridazin-4-amine

Conditions	Yield
In isopropyl alcohol at 120℃; for 0.666667h; Microwave irradiation; Sealed tube; regioselective reaction;	90%

3,4,6-trichloropyridazine (6082-66-2) + 3-Phenylpropan-1-amine (2038-57-5) → 3,6-dichloro-N-(3-phenylpropyl)pyridazin-4-amine

Conditions	Yield
In isopropyl alcohol at 120℃; for 0.333333h; Microwave irradiation; Sealed tube; regioselective reaction;	89%

3,3-dimethyl azetidine (19816-92-3) + 3,4,6-trichloropyridazine (6082-66-2) → 3,6-dichloro-4-(3,3-dimethylazetidin-1-yl)pyridazine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 3h;	88.15%

3,4,6-trichloropyridazine (6082-66-2) + 4-Fluorobenzenesulfonyl chloride (349-88-2) → N-(3,6-dichloropyridazin-4-yl)-4-fluorobenzenesulfonamide (1162681-01-7)

Conditions	Yield
Stage #1: 3,4,6-trichloropyridazine With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 4-Fluorobenzenesulfonyl chloride In tetrahydrofuran at 0℃; for 1h; Stage #3: With water; ammonium chloride In tetrahydrofuran	86.7%

3,4,6-trichloropyridazine (6082-66-2) + 2-methyl-6-(methylsulfonyl)pyridin-3-amine (897732-75-1) → 3,6-dichloro-N-(2-methyl-6-(methylsulfonyl)pyridin-3-yl)pyridazin-4-amine (1236355-11-5)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 16h;	84%

3,4,6-trichloropyridazine (6082-66-2) + 4-bromo-3,6-dichloro-pyridazine (10344-42-0) → 2-[(3,6-dichloropyridazin-4-yl)oxy]ethan-1-ol (17284-80-9)

Conditions	Yield
Stage #1: ethylene glycol With sodium hydride In tetrahydrofuran at 0℃; for 0.666667h; Stage #2: 3,4,6-trichloropyridazine; 4-bromo-3,6-dichloro-pyridazine In tetrahydrofuran at 0 - 20℃;	83%

3,4,6-trichloropyridazine (6082-66-2) → 2-[(3,6-dichloropyridazin-4-yl)oxy]ethan-1-ol (17284-80-9)

Conditions	Yield
Stage #1: ethylene glycol With sodium hydride In tetrahydrofuran at 0℃; for 0.666667h; Stage #2: 3,4,6-trichloropyridazine In tetrahydrofuran at 0 - 20℃;	83%
Stage #1: ethylene glycol With sodium hydride In tetrahydrofuran at 0℃; for 0.666667h; Stage #2: 3,4,6-trichloropyridazine In tetrahydrofuran at 0 - 20℃;
Stage #1: ethylene glycol With sodium hydride In tetrahydrofuran at 0℃; for 0.666667h; Stage #2: 3,4,6-trichloropyridazine In tetrahydrofuran at 0 - 20℃;

3,4,6-trichloropyridazine (6082-66-2) + ethylene glycol (107-21-1) → 2-[(3,6-dichloropyridazin-4-yl)oxy]ethan-1-ol (17284-80-9)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃;	83%
Stage #1: ethylene glycol With sodium hydride In tetrahydrofuran at 0℃; for 0.666667h; Stage #2: 3,4,6-trichloropyridazine In tetrahydrofuran at 0 - 20℃;	83%
Stage #1: ethylene glycol With sodium hydride In tetrahydrofuran at 0℃; for 0.666667h; Stage #2: 3,4,6-trichloropyridazine In tetrahydrofuran at 0 - 20℃;	83%

(3-chloro-5-trifluoromethyl-pyridin-2-yl)methylamine (175277-74-4) + 3,4,6-trichloropyridazine (6082-66-2) → C11H6Cl3F3N4

Conditions	Yield
With triethylamine In methanol at 20℃;	82.2%

3,4,6-trichloropyridazine (6082-66-2) + allyl alcohol (107-18-6) → 3,4,6-trichloropyridazine (1417848-60-2)

Conditions	Yield
With caesium carbonate In acetonitrile at 20 - 65℃;	80%
With sodium hydride

3,4,6-trichloropyridazine (6082-66-2) + Benzhydrylamine (91-00-9) → N-benzhydryl-3,6-dichloropyridazin-4-amine

Conditions	Yield
In isopropyl alcohol at 130℃; for 12h; Microwave irradiation; Sealed tube; regioselective reaction;	80%

3,4,6-trichloropyridazine (6082-66-2) + benzene-1,2-diol (120-80-9) → 3-chlorobenzo[5,6][1,4]dioxino[2,3-c]pyridazine

Conditions	Yield
Stage #1: benzene-1,2-diol With sodium hydride In 1,2-dimethoxyethane at 0℃; for 0.5h; Stage #2: 3,4,6-trichloropyridazine In 1,2-dimethoxyethane for 2h; Reflux;	80%

3,4,6-trichloropyridazine (6082-66-2) + tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (144222-22-0) → tert-butyl 4-(((3,6-dichloropyridazin-4-yl)amino)methyl)piperidine-1-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃;	79%
In tetrahydrofuran at 100℃;	26%

4-piperidinemethanol (6457-49-4) + 3,4,6-trichloropyridazine (6082-66-2) → [1-(3,6-dichloropyridazin-4-yl)piperidin-4-yl]methanol (1349874-35-6)

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 100℃;	75.99%

1-(2-hydroxyethyl)piperazine (103-76-4) + 3,4,6-trichloropyridazine (6082-66-2) → 2-(4-(3,6-dichloropyridazin-4-yl)piperazin-1-yl)ethanol (921769-61-1)

Conditions	Yield
With sodium carbonate In N,N-dimethyl acetamide at 20℃; for 12h; Inert atmosphere;	73.6%
With sodium carbonate In N,N-dimethyl acetamide at 20℃;	73.6%

3,4,6-trichloropyridazine (6082-66-2) + 2-(thiomorpholino)ethanethiol (42302-19-2) → 3,6-dichloro-4-[2-(4-thiomorpholino)ethanesulfanyl]pyridazine

Conditions	Yield
With potassium carbonate In acetonitrile for 20h; Heating;	72%

Upstream product

• 5397-64-8 4-chloro-1,2-dihydro-pyridazine-3,6-dione 
• 15456-86-7 4-bromo-1,2-dihydropyridazine-3,6-dione 
• 141-30-0 3,6-dichlorpyridazine 
• 30480-35-4 pyridazine-3,4,6-triol 
• 15456-86-7 4-Brom-pyridazin-3,6-diol 
• 5926-51-2 bromomaleic anhydride 

Downstream Products

• 823-58-5 3,6-dichloropyridazin-4-amine 
• 921769-61-1 2-(4-(3,6-dichloropyridazin-4-yl)piperazin-1-yl)ethanol 
• 2779-81-9 3,6-dichloropyridazin-4-ol 
• 36096-74-9 4-(3,6-Dichloropyridazine-4-yl)morpholine 
• 1553904-41-8 4-(benzyloxy)-3,6-dichloropyridazine 
• 70952-62-4 3,6-dichloro-4-methoxy-1,2-dihydropyridazine 
• 32905-93-4 N,N-dibenzyl-3,6-dichloropyridazin-4-amine 
• 6885-89-8 4,6-dichloro-2-methylpyridazin-3-(2H)-one 
• 6794-35-0 5,6-dichloro-2-methylpyridazin-3-(2H)-one 
• 10338-17-7 3,6-dichloro-N-phenylpyridazin-4-amine 
• 17645-06-6 3,6-dichloro-N-methyl-pyridazin-4-amine 
• 130619-04-4 3,6-dichloro-4-((4-(4-(2-methoxyphenyl)-1-piperazinyl)butyl)amino)pyridazine 
• 770718-68-8 C₁₃H₁₃Cl₂N₃O 
• 943025-98-7 4-bromo-2-{[4-(methyloxy)phenyl]methyl}-6-({[4-(methyloxy)phenyl]methyl}oxy)-3(2H)-pyridazinone 

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