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CAS No. : | 89193-22-6 | MDL No. : | MFCD20441530 |
Formula : | C6H10N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HAJMFBQNIMHGFE-UHFFFAOYSA-N |
M.W : | 126.16 | Pubchem ID : | 12498505 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 35.44 |
TPSA : | 38.05 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.59 cm/s |
Log Po/w (iLOGP) : | 1.43 |
Log Po/w (XLOGP3) : | 0.68 |
Log Po/w (WLOGP) : | 0.74 |
Log Po/w (MLOGP) : | 0.11 |
Log Po/w (SILICOS-IT) : | 0.72 |
Consensus Log Po/w : | 0.74 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.46 |
Solubility : | 4.36 mg/ml ; 0.0345 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.06 |
Solubility : | 11.1 mg/ml ; 0.0879 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.95 |
Solubility : | 14.0 mg/ml ; 0.111 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.69 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P270-P301+P312+P330-P501 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
97.74% | Step D: A flask was charged with <strong>[89193-22-6]1,3,5-trimethyl-1H-pyrazol-4-ol</strong> (10.46 g, 82.89 mmol), and DMF:dioxane (9: 1 ) (700 taunL). The reaction mixture was cooled to 0 C and 60% sodium hydride (3.3 15 g, 82.89 mmol) was added portionwise. The reaction mixture was stirred for 15 minutes, and 5-bromo-3-nitropicoIinonitrile (18 g, 78.95 mmol) was added. The reaction was stirred at ambient temperature for 3 hours, then poured slowly into 600 mL water and stirred for 10 minutes. The resultant solids were filtered and dried to afford 5- bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile (23.70 g, 97.74 % yield) as very lightly tan (white) solid.; Step D: A flask was charged with 1,3,S-trimethyl-1H-pyrazol-4-ol (10.46 g, 82.89 mmol), and added DMF:dioxane (9:1) (700 mL). The reaction mixture was cooled to 0 C and 60% sodium hydride (3.315 g, 82.89 mmol) was added portionwise and the reaction was stirred for 15 minutes. 5-Bromo-3-nitropicolinonitriIe ( 18 g, 78.95 mmol) was added and the reaction was stirred at ambient temperature for 3 hours. The reaction was poured slowly into 600 mL water and stirred for 10 minutes. The resultant solids were filtered and dried to afford 5-bromo-3-(1,3,5-trimethyl-1H-pytauazol-4-yloxy)picolinonitrile (23.70 g, 97.74 % yield) as very lightly tan (white) solid.; Step D: A flask was charged with <strong>[89193-22-6]1,3,5-trimethyl-1H-pyrazol-4-ol</strong> (10.46 g, 82.89 mmol), and DMFrdioxane (9: 1) (700 mL). The reaction mixture was cooled to 0 C and 60% sodium hydride (3.315 g, 82.89 mmol) was added portionwise. The reaction mixture was stirred for 15 minutes, then 5-bromo-3-nitropicolinonitrile (18 g, 78.95 mmol) was added and the reaction was stirred at ambient temperature for 3 hours. The reaction was poured slowly into 600 mL water and stirred for 10 minutes. The resultant solids were filtered and dried to afford 5-bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile (23.70 g, 97.74 % yield) as very lightly tan (white) solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With sodium hydroxide; ethanol; water; at 20℃; for 2h; | Step C: A flask was charged with 1,3,5-trimethyl-1H-pyrazol-4-yI benzoate (80 g, 347 mmol), and added 500 mL ethanol. 3M NaOH (174 ml, 521 mmol) was added and the reaction was stirred at ambient temperature for 2 hours. The ethanol was removed in vacuo and the aqueous layer was extracted with dichloromethane, ethyl acetate and <n="115"/>dichloromethane.isopropyl alcohol (4:1). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford 1,3,5-trinaethyl-1H-pyrazol-4-ol (34 g, 78 % yield) as white solid.; Step C: A flask was charged with 1,3,5-trimethyl-1H-pyrazol-4-yl benzoate (80 g, 347 mmol), and 500 mL ethanol was added. 3M NaOH (174 ml, 521 mmol) was added and the <n="118"/>reaction was stirred at ambient temperature for 2 hours. The ethanol was removed in vacuo and the aqueous layer was extracted with dichloromethane, ethyl acetate and dichloromethaneiisopropy] alcohol (4:1). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford 1,3,5-trimethyl-1H-pyrazol-4-ol (34 g, 78 % yield) as white solid.; Step C: A flask was charged with 1,3,5-trimethyl-1H-pyrazol-4-yl benzoate (80 g, 347 mmol), and 500 mL ethanol. To the above mixture was added 3M NaOH (174 ml, 521 mmol) and stirred at ambient temperature for 2 hours. The ethanol was removed in vacuo and the aqueous layer was extracted with dichloromethane, ethyl acetate and dichloromethane:isopropyl alcohol (4:1). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford 1,3,5-trimethyl-1H-pyrazol-4-ol (34 g, 78 % yield) as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.969 g | With potassium carbonate; In ethyl acetate; toluene; at 10 - 80℃; for 2h; | (A) Ethyl 4-oxo-3-((1,3,5-trimethyl-1H-pyrazol-4-yl)oxy)-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxylate To a mixed solution of ethyl 3-(methylsulfonyl)-4-oxo-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxylate (1.0 g) and ethyl acetate (5.0 mL)/toluene (5.0 mL), <strong>[89193-22-6]1,3,5-trimethyl-1H-pyrazol-4-ol</strong> (0.459 g) and potassium carbonate (2.297 g) were added at room temperature, and then the reaction mixture was stirred at 80 C for 2 hours. The reaction mixture was added to water at room temperature and then extracted with ethyl acetate. The extract was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (0.969 g). MS: [M+H]+ 349.0. |
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