| Identification | More | [Name]
3,6-Dichloro-4-methylpyridazine | [CAS]
19064-64-3 | [Synonyms]
3,6-DICHLORO-4-METHYLPYRIDAZINE
4-METHYL-3,6-DICHLOROPYRIDAZINE
BUTTPARK 47\04-25
3,6-Dichloro-5-methylpyridazine | [EINECS(EC#)]
242-794-3 | [Molecular Formula]
C5H4Cl2N2 | [MDL Number]
MFCD00006465 | [Molecular Weight]
163 | [MOL File]
19064-64-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Brown crystalline powder. | [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 | [form ]
Crystalline Powder | [pka]
-0.56±0.10(Predicted) | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29339980 |
| Hazard Information | Back Directory | [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. | [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 |
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