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CAS No. : | 943026-40-2 | MDL No. : | MFCD09907908 |
Formula : | C6H5ClN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PVPVPUGHBYWWMK-UHFFFAOYSA-N |
M.W : | 172.57 | Pubchem ID : | 55267440 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H320-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
77% | With lithium hydride In 1,4-dioxane at 20℃; for 1 h; | (c) 3-Chloro-6,7-dihydro[1,4]dioxino[2,3-c]pyridazineA solution of 2-[(3,6-dichloro-4-pyridazinyl)oxy]ethanol containing some bromo-derivative (15.46 g; 0.0703 mol) in dry dioxan (1.2 L) was treated with lithium hydride (2.3 g; 0.28 mol) in portions and stirred at room temperature for 1 hour under argon, then heated at 110° C. overnight. The reaction mixture was quenched with wet dioxan, then iced-water. The solution was evaporated to half volume, taken to pH 8 with 5M hydrochloric acid and evaporated to dryness. Water was added and the residue was extracted 5.x. with chloroform, dried (sodium sulphate) and evaporated to afford a white solid (12.4 g, ca. 77percent) (containing ca. 15percent of a bromo species).MS (+ve ion electrospray) m/z 173/5 (Cl MH+); 217/9 (Br MH+) |
77% | With lithium hydride In 1,4-dioxane at 20 - 110℃; | (c) 3-Chloro-6,7-dihydro[l,4]dioxino[2,3-c]pyridazine; A solution of 2-[(3,6-dichloro-4-pyridazinyl)oxy]ethanol containing some bromo-derivative (15.46 g; 0.0703 mol) in dry 1,4-dioxane (1.2 L) was treated with lithium hydride (2.3 g; 0.28 mol) in portions and stirred at room temperature for 1 hour under argon, then heated at 110 0C overnight. The reaction mixture was quenched with wet 1 ,4-dioxane, then iced-water. The solution was evaporated to half volume, taken to pH 8 with 5M hydrochloric acid and evaporated to dryness. Water was added and the residue was extracted 5x with chloroform, dried (sodium sulphate) <n="34"/>and evaporated to afford a white solid (12.4 g, ca.77percent) (containing ca. 15percent of a bromo species).MS (+ve ion electrospray) m/z 173/5 (Cl MH+); 217/9 (Br MH+) |
77% | With lithium hydride In 1,4-dioxane at 20 - 110℃; | (j) 3-Chloro-6,7-dihydro[l,4]dioxino[2,3-c]pyridazine; A solution of 2-[(3,6-dichloro-4-pyridazinyl)oxy]ethanol containing some bromo- derivative (15.46 g; 0.0703 mol) in dry 1,4-dioxane (1.2 L) was treated with lithium hydride (2.3 g; 0.28 mol) in portions and stirred at room temperature for 1 hour under argon, then heated at 110 0C overnight. The reaction mixture was quenched with wet 1,4- dioxane, then iced- water. The solution was evaporated to half volume, taken to pH 8 <n="56"/>with 5M hydrochloric acid and evaporated to dryness. Water was added and the residue was extracted 5x with chloroform, dried (sodium sulphate) and evaporated to afford a white solid (12.4 g, ca.77percent) (containing ca. 15percent of a bromo species). MS (+ve ion electrospray) m/z 173/5 (Cl MH+); 217/9 (Br MH+). |
77% | With lithium hydride In 1,4-dioxane at 20 - 110℃; | (c) 3-Chloro-6,7-dihydro[l,4]dioxino[2,3-c]pyridazine; A solution of 2-[(3,6-dichloro-4-pyridazinyl)oxy]ethanol containing some bromo- derivative (15.46 g; 0.0703 mol) in dry 1,4-dioxane (1.2 L) was treated with lithium hydride (2.3 g; 0.28 mol) in portions and stirred at room temperature for 1 hour under argon, then heated at 110 0C overnight. The reaction mixture was quenched with wet 1,4- dioxane, then iced- water. The solution was evaporated to half volume, taken to pH 8 with 5M hydrochloric acid and evaporated to dryness. Water was added and the residue was extracted 5x with chloroform, dried (sodium sulphate) and evaporated to afford a white solid (12.4 g, ca.77percent) (containing ca. 15percent of a bromo species). MS (+ve ion electrospray) m/z 173/5 (Cl MH+); 217/9 (Br MH+) |
55% | With sodium hydride In tetrahydrofuran at 80℃; for 72 h; | (c) 3-Chloro-6,7-dihydro[l,4]dioxino[2,3-c]pyridazine; A solution of 2-[(3,6-dichloro-4-pyridazinyl)oxy]ethanol (5.5g) in tetrahydrofuran (4.5 litres) was treated with sodium hydride (60percent dispersion in oil, 8g) and heated at 80 deg C for 72 hours. The reaction mixture was quenched with wet tetrahydrofuran then ice and evaporated to dryness. The residue was chromatographed on silica eluting with 0- 100percent ethyl acetate in hexane affording a white solid (2.5g, 55percent) containing some bromo species (5percent). MS (+ve ion electrospray) m/z 173 (MH+). |
33% | With sodium hydride In 1,4-dioxane at 110℃; for 18 h; | To a solution of 2-[(3,6-dichloropyridazin-4-yl)oxy]ethan-1-ol 49a (4.52 g, 21.61 mmol) in 1 , 4-dioxane (250 ml_) was added NaH (60percent, 2.07 g, 86.44 mmol) and the reaction heated to 1 10°C for 18 h. After cooling, the reaction was quenched with iced water, reduced in volume and extracted with DCM (3 x 75 ml_). The combined organic extracts were washed with H2O, dried over MgS04 and concentrated. The crude material was purified by silica gel chromatography eluting with 0-3percent MeOH in EtOAc to give 3-chloro-6H,7H-[1 ,4]dioxino[2,3- c) pyridazine 49b (1.22 g, 33percent). LC-MS (Method A) 173.0 [M+H]+ 1.27 min. |
[ 1256038-18-2 ]
3-Chloro-5-(2-methoxyethoxy)pyridazine
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