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CAS No. : | 17973-86-3 | MDL No. : | MFCD00233947 |
Formula : | C4H2Br2N2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | VQAFMTSSCUETHA-UHFFFAOYSA-N |
M.W : | 237.88 | Pubchem ID : | 248852 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In monoethylene glycol diethyl ether; water; at 80℃; for 17h; | Intermediate 2: 3-Bromo-6-(2,3-dichlorophenyl)pyridazine.To a suspension of 3,6-dibromopyridazine (5g, 21mmol) in ethylene glycol dimethyl ether (100ml) was added 2,3-dichlorophenyl boronic acid (4.03g, 21mmol), tetrakis(triphenylphosphine)palladium(0) (1.2g, 1.05mmol) and sodium carbonate (2N, aqueous) (50ml), the mixture was then heated to 800C for 17 hours whilst under argon. The dark crude reaction mixture was then evaporated to dryness. The residue was partitioned between water (200ml) and dichloromethane (300ml). The aqueous layer was separated and further extracted with dichloromethane (200ml). The combined dichloromethane layers were evaporated and the residue was purified by chromatography (90g of silica) eluting with 75% dichloromethane/ petroleum ether 40:60. The title compound was obtained as a pink coloured solid (680mg). 1H-NMR (CDCl3) ? 7.38 (IH, X, J= 8), 7.58-7.63 (2H, m), 7.70-7.76 (2H, m) LC/MS m/z [MH+] 305 consistent with molecular formula C10H581Br35Cl2N2 | |
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80℃; for 17h; | To a suspension of 3,6-dibromopyridazine (5g, 21mmol) in ethylene glycol dimethyl ether (100ml) was added 2,3-dichlorophenyl boronic acid (4.03g, 21mmol), tetrakis(triphenylphosphine)palladium(0) (1.2g, 1.05mmol) and sodium carbonate (2N, aqueous) (50ml), the mixture was then heated to 800C for 17 hours whilst under argon. The dark crude <n="169"/>reaction mixture was then evaporated to dryness. The residue was partitioned between water (200ml) and dichloromethane (300ml). The aqueous layer was separated and further extracted with dichloromethane (200ml). The combined dichloromethane layers were evaporated and the residue was purified by chromatography (9Og of silica) eluting with 75% dichloromethane/ petroleum ether 40:60. The title compound was obtained as a pink coloured solid (680mg). 1H-NMR (CDCl3) δ 7.38 (IH, t, /= 8), 7.58-7.63 (2H, m), 7.70-7.76 (2H, m) LC/MS m/z [MH+] 305 consistent with molecular formula Ci0H581Br35Cl2N2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
277. 8 mg (2.1 mmol) of hydroxyacetic acid tert-butyl ester and 100.9 mg of sodium hydride (55 percent in mineral oil) in 15 ml of DMF were stirred at room temperature for 30 min. Then 500 mg (2.1 mmol) of 3,6-dibrompyridazine were added, and the reaction mixture was stirred at 60 °C for 2 h. After evaporation to dryness, the residue was stirred with ethyl acetate, the solution filtered, evaporated, and the crude product (450 mg) directly employed in the subsequent step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61.2% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 120℃; for 12h;Inert atmosphere; | 1) Weigh 0.05 mol of 3,6-dibromopyridazine in a 250 ml three-vial bottle.0.12 mol of <strong>[197223-39-5](3,5-di-tert-butylphenyl)boronic acid</strong> and 100 ml of toluene were stirred and dissolved, and under the protection of nitrogen, 0.0025 mol of Pd(PPh3)4 and 0.1 mol of potassium carbonate were added.50ml water and ethanol volume ratio of 1:1 mixed solution, stirring heated to 120 ° C, refluxing reaction for 12 hours, sampling point board, significantShows no 3,6-dibromopyridazine remaining, the reaction is complete; naturally cooled to room temperature, filtered, the filtrate layered, the organic phase was taken for vacuumDistilled to zero fractions, over neutral silica gel column to give Intermediate 3-1, HPLC purity 99.3percent, yield 61.2percent; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With triethylamine; In acetonitrile; at 160℃; for 1.66667h;Microwave irradiation; | 3,6-Dibromopyridazine (0.2 g, 0.841 mmol) was dissolved in acetonitrile (2.5 ml_). Then 8-oxa-3- azabicyclo[3.2.1]octane (0.105 g, 0.925 mmol) and triethylamine (0.176 ml_, 1.261 mmol) were added and the suspension was irradiated in the microwave to 160C for 1 h and 20 minutes. The reaction mixture was diluted with dichloromethane and water. The organic layer was separated and the aqueous layer was extracted with dichloromethane twice. The combined organic layers were dried over Na2S04, filtered and concentrated under reduced pressure. The crude product was purified on a silica gel column using a Biotage Isolera One purification system employing an n-heptane/ethyl acetate gradient (100/0 -> 0/100) to afford the title compound as a beige solid (0.152 g, 67 %). (0609) MS: 271.5 (M+H)+. (0610) 1H-NMR (400 MHz, Chloroform-d) d = 7.32 (d, J = 9.5 Hz, 1 H), 6.70 (d, J = 9.5 Hz, 1 H), 4.60 - 4.43 (m, 2H), 3.83 (d, J = 12.8 Hz, 2H), 3.23 (dd, J = 12.4, 2.7 Hz, 2H), 2.08 - 1.94 (m, 2H), 1.90 - 1.76 (m, 2H). |
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