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| | 3,6-Dichloro-4-methylpyridazine Basic information |
| Product Name: | 3,6-Dichloro-4-methylpyridazine | | Synonyms: | BUTTPARK 47\04-25;3,6-DICHLORO-4-METHYLPYRIDAZINE;4-METHYL-3,6-DICHLOROPYRIDAZINE;3,6-Dichloro-5-methylpyridazine;3,6-Dichloro-4-Methyl-pyr...;3,6-Dichloro-4-methylpyridazine,97%;3,6-Dichloro-4-Methy;3,6-Dichloro-4-methyl-1,2-diazine | | CAS: | 19064-64-3 | | MF: | C5H4Cl2N2 | | MW: | 163 | | EINECS: | 242-794-3 | | Product Categories: | Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Halides;Pyrazines, Pyrimidines & Pyridazines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridazines;PyridazinesHeterocyclic Building Blocks;pyridazine | | Mol File: | 19064-64-3.mol |  |
| | 3,6-Dichloro-4-methylpyridazine Chemical Properties |
| Melting point | 86-88 °C (lit.) | | Boiling point | 149-151 °C/21 mmHg (lit.) | | density | 1.5462 (rough estimate) | | refractive index | 1.6300 (estimate) | | Fp | 149-151°C/21mm | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Methanol | | pka | -0.56±0.10(Predicted) | | form | Crystalline Powder | | color | Brown | | BRN | 119573 | | InChI | InChI=1S/C5H4Cl2N2/c1-3-2-4(6)8-9-5(3)7/h2H,1H3 | | InChIKey | ROYHWGZNGMXQEU-UHFFFAOYSA-N | | SMILES | C1(Cl)=NN=C(Cl)C=C1C | | CAS DataBase Reference | 19064-64-3(CAS DataBase Reference) | | NIST Chemistry Reference | Pyridazine, 3,6-dichloro-4-methyl-(19064-64-3) |
| Hazard Codes | Xi,Xn | | Risk Statements | 36/37/38-20/21/22 | | Safety Statements | 26-37/39-36/37/39-22 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29339980 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 3,6-Dichloro-4-methylpyridazine Usage And Synthesis |
| Chemical Properties | Brown crystalline powder. | | Uses | 3,6-Dichloro-4-methylpyridazine has been used in the synthesis of 7-methyl-2-phenylimidazo[1,2-b]pyridazine-3-carboxylic acid. | | Application |
3,6-Dichloro-4-methylpyridazine is mainly used as an intermediate in pesticides and pharmaceuticals.
| | Hazard |
3,6-Dichloro-4-methylpyridazine causes skin irritation and serious eye irritation, it may cause respiratory irritation.
| | Synthesis | 4-Methyl-1,2-dihydropyridazine-3,6-dione (9.48 g, 75.2 mmol) was suspended in phosphoryl chloride (70 mL, 750 mmol) under nitrogen protection and stirred at room temperature. Subsequently, the reaction mixture was heated to a mild reflux condition and maintained for 4 hours until a golden yellow homogeneous solution was formed. Upon completion of the reaction, the mixture was cooled and the excess trichlorophosphorus was removed by distillation under reduced pressure (14 mbar, 50-70°C). The resulting viscous brown oil was slowly added dropwise to an ice-cooled saturated sodium bicarbonate solution (200 mL) while stirring vigorously. The pH of the mixture was adjusted to 6 by batchwise addition of solid sodium bicarbonate, followed by extraction with ethyl acetate (2 x 60 mL). The organic phases were combined, washed with saturated sodium bicarbonate solution (30 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford 3,6-dichloro-4-methylpyridazine (11.5 g, 70.8 mmol, 94% yield) as a yellow powder. The product was recrystallized from light petroleum ether/ether and had a melting point of 87-88°C. IR spectrum (KBr, cm^-1): 3054, 1567, 1434, 1351, 1326, 1145, 1121, 914, 720. NMR hydrogen spectrum (200 MHz, CDCl3): δ 2.42 (3H, d, J = 1.0 Hz), 7.41 ( 1H, q, J = 0.9 Hz). NMR carbon spectrum (50 MHz, CDCl3): δ 19.2 (CH3), 130.1 (CH-5), 140.7 (C-4), 155.6 (C-6), 157.3 (C-3). Low resolution mass spectrum (EI): m/z 162 ([M+]). Calculated elemental analysis (C5H4Cl2N2): C, 36.84; H, 2.47; N, 17.19. Measured values: C, 36.93; H, 2.57; N, 17.48. | | References | [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 5, p. 1644 - 1658
[2] Journal of the American Chemical Society, 1954, vol. 76, p. 2201
[3] Pharmaceutical Bulletin, 1957, vol. 5, p. 587,588
[4] Helvetica Chimica Acta, 1954, vol. 37, p. 121,131
[5] Journal of the American Chemical Society, 1954, vol. 76, p. 4454,4457 |
| | 3,6-Dichloro-4-methylpyridazine Preparation Products And Raw materials |
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