| Identification | Back Directory | [Name]
3-bromo-6-methylpyridazine | [CAS]
65202-58-6 | [Synonyms]
3-bromo-6-methylpyridazine
6-Methyl-3-broMopyridazine
Pyridazine, 3-broMo-6-Methyl-
3-bromo-6-methylpyridazine ISO 9001：2015 REACH
3-bromo-6-methylpyridazine 6-Methyl-3-broMopyridazine | [Molecular Formula]
C5H5BrN2 | [MDL Number]
MFCD09831907 | [MOL File]
65202-58-6.mol | [Molecular Weight]
173.01 |
| Chemical Properties | Back Directory | [Boiling point ]
285.0±20.0 °C(Predicted) | [density ]
1.596±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
1.26±0.10(Predicted) | [color ]
Dark Brown | [InChI]
InChI=1S/C5H5BrN2/c1-4-2-3-5(6)8-7-4/h2-3H,1H3 | [InChIKey]
RACIHBXDZONTQJ-UHFFFAOYSA-N | [SMILES]
C1(Br)=NN=C(C)C=C1 |
| Hazard Information | Back Directory | [Uses]
3-Bromo-6-methylpyridazine is used as a reagent in the synthesis of piperazinyl quinolines as chemosensitizers to increase fluconazole susceptibility of Candida albicans. 3-Bromo-6-methylpyridazine is also used in the preparation of cyclohexyl fluoropyrimidinyl benzamides as CNS penetrable P2X7 receptor antagonists. | [Synthesis]
6-Methyl-3(2H)-pyridazinone (18 g, 163.44 mmol) was mixed with phosphorus tribromide oxide (93.8 g, 327.6 mmol) and the reaction was stirred at 70 °C overnight. Upon completion of the reaction, the reaction mixture was cooled to 40 °C and quenched by slowly pouring it into ice water. Subsequently, the reaction mixture was neutralized with saturated sodium bicarbonate solution (20 mL) and extracted with dichloromethane (100 mL x 3). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target product 3-bromo-6-methylpyridazine (8 g, 31% yield). The product was detected by LCMS (ESI), m/z: 173 [M + 1]+. 1H NMR (chloroform-d, Bruker Avance 400MHz) data were as follows: δ 7.86-7.88 (d, 1H, J = 8Hz), 7.52-7.54 (d, 1H, J = 8Hz), 2.55 (s, 3H). | [References]
[1] Patent: EP3333157, 2018, A1. Location in patent: Paragraph 0136; 0137
[2] Patent: WO2010/36998, 2010, A2. Location in patent: Page/Page column 184 |
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