4,5-DICHLORO-2-METHYLPYRIDAZIN-3-ONE Chemical Properties

Melting point:

87-91 °C(lit.)

Boiling point:

197.2±50.0 °C(Predicted)

Density 

1.55±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

soluble in Ethanol

form 

powder to crystal

pka

-3.57±0.20(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C5H4Cl2N2O/c1-9-5(10)4(7)3(6)2-8-9/h2H,1H3

InChIKey

ACKBTCUMGAHRIE-UHFFFAOYSA-N

SMILES

C1(=O)N(C)N=CC(Cl)=C1Cl

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38-43

Safety Statements 

26-36

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

UR6188000

HazardClass 

6.1

HS Code 

29339980

MSDS

• Language:English Provider:SigmaAldrich

4,5-DICHLORO-2-METHYLPYRIDAZIN-3-ONE Usage And Synthesis

Chemical Properties

Off-white to yellow low crystalline powder

Uses

4,5-Dichloro-2-methyl-3(2H)-pyridazinone can be used in the synthesis of 4-amino-3(2H)-pyridazinones and 5-amino-3(2H)-pyridazinones via reaction with N-benzylaminoethanol.

Definition

ChEBI: 4,5-Dichloro-2-methyl-3(2H)-pyridazinone is a pyridazinone.

Synthesis

Step 1: A round bottom flask was charged with 4,5-dichloropyridazin-3(2H)-one (10.0 g, 60.6 mmol), potassium carbonate (16.8 g, 121.2 mmol), iodomethane (4.0 mL, 64.3 mmol) and acetonitrile (80 mL). The reaction mixture was heated to reflux for 12 hours and then cooled to room temperature. After completion of the reaction, the mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (dichloromethane as eluent) to afford 4,5-dichloro-2-methylpyridazin-3-one 8.21 g (76% yield). The product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 8.18 (s, 1H), 3.70 (s, 3H); mass spectrum (m/z) = 179 ([M+H]+).

References

[1] Patent: WO2009/142732, 2009, A2. Location in patent: Page/Page column 61-62
[2] Patent: WO2011/15629, 2011, A1. Location in patent: Page/Page column 46; 47
[3] Journal of Heterocyclic Chemistry, 1996, vol. 33, # 6, p. 1579 - 1582
[4] Patent: WO2013/50421, 2013, A1. Location in patent: Page/Page column 37
[5] Journal of the Korean Chemical Society, 2014, vol. 58, # 1, p. 140 - 144

4,5-DICHLORO-2-METHYLPYRIDAZIN-3-ONE(933-76-6)Related Product Information

• 4,5-DICHLORO-2-(2-FLUOROBENZYL)PYRIDAZINE-3(2H)-ONE
• 2-(2-CHLORO-6-FLUOROBENZYL)-4,5-DICHLOROPYRIDAZINE-3-(2H)-ONE
• 1-PHENYL-4,5-DICHLORO-6-PYRIDAZONE
• 4,5-DICHLORO-2-(3,5-DICHLOROPHENYL)-2,3-DIHYDROPYRIDAZIN-3-ONE
• 4,5-DICHLORO-2-METHYLPYRIDAZIN-3-ONE
• 4,5-DICHLORO-2-(4-METHYLBENZYL)-2,3-DIHYDROPYRIDAZIN-3-ONE
• 4,5-DICHLORO-2-(HYDROXYMETHYL)-2,3-DIHYDROPYRIDAZIN-3-ONE
• 2-CHLOROMETHYL-4,5-DICHLOROPYRIDAZIN-3(2H)-ONE
• 4,5-dichloro-2-[3-(trifluoromethyl)phenyl]pyridazin-3(2H)-one
• 4,5-DICHLORO-2-(4-METHYLPHENYL)-2,3-DIHYDROPYRIDAZIN-3-ONE
• 2-(3-CHLORO-4-FLUOROPHENYL)-4,5-DICHLORO-PYRIDAZINE-3-(2H)-ONE
• 4,5-DICHLORO-2-(2,6-DICHLOROBENZYL)-2,3-DIHYDROPYRIDAZIN-3-ONE
• 4,5-DICHLORO-2-(2,4-DICHLOROPHENYL)-2,3-DIHYDROPYRIDAZIN-3-ONE
• 2-BENZYL-4,5-DICHLORO-2,3-DIHYDROPYRIDAZIN-3-ONE
• 4,5-DICHLORO-2-(4-CHLOROBENZYL)-2,3-DIHYDROPYRIDAZIN-3-ONE
• 4,5-DICHLORO-6-HYDROXY-2-(2-HYDROXYETHYL)-2,3-DIHYDROPYRIDAZIN-3-ONE
• (4,5-DICHLORO-6-OXO-1,6-DIHYDROPYRIDAZIN-1-YL)METHYL BENZOATE
• 4,5-DICHLORO-6-HYDROXY-2-[2-HYDROXY-3-(METHYLTHIO)PROPYL]-2,3-DIHYDROPYRIDAZIN-3-ONE