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CAS No. : | 1703-07-7 | MDL No. : | MFCD04971427 |
Formula : | C5H5ClN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UGDOVAWXAHZLEV-UHFFFAOYSA-N |
M.W : | 144.56 | Pubchem ID : | 164871 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 34.83 |
TPSA : | 45.75 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) : | -6.68 cm/s |
Log Po/w (iLOGP) : | 1.25 |
Log Po/w (XLOGP3) : | 0.71 |
Log Po/w (WLOGP) : | 0.73 |
Log Po/w (MLOGP) : | 0.79 |
Log Po/w (SILICOS-IT) : | 2.17 |
Consensus Log Po/w : | 1.13 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.68 |
Solubility : | 3.04 mg/ml ; 0.021 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.25 |
Solubility : | 8.15 mg/ml ; 0.0564 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.54 |
Solubility : | 0.418 mg/ml ; 0.00289 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.93 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
18% | Stage #1: at 110 - 115℃; for 3 h; Stage #2: With sodium hydrogencarbonate In water |
3,6-Dichloro-4-methylpyridazine (30.6 g, 190 mmol) was suspended in glacial AcOH (800 mL) at ambient temperature and heated in an oil bath thermostatted at 110-115 °C for 3 h. (The mixture became homogenous after 1 h.) The mixture was allowed to cool and the AcOH was removed by vacuum distillation. The resulting solid residue was slowly treated with sat. NaHCO3 solution (200 mL) to give a pale yellow heterogenous mixture that was adjusted to pH 6 by the slow addition of solid NaHCO3 with vigorous stirring. The mixture was extracted with dichloromethane (2 x 250 mL) and the combined organic phase was washed with sat. NaCl solution (60 mL), dried (MgSO4) and evaporated to afford a solid (20.9 g). The crude material was subjected to column chromatography (gradient 1percent MeOH/CH2Cl2 to 5percent MeOH/CH2Cl2) to afford, 6-chloro-4-methyl-2H-pyridazin-3-one (13.4 g, 92.7 mmol; 49percent) [Rf 0.21 (2.5percent MeOH/CH2Cl2)] and 6-chloro-5-methyl-2H-pyridazin-3-one (5.00 g, 34.6 mmol; 18percent) [Rf 0.11 (2.5percent MeOH/CH2Cl2)] as a colourless solids. 6-Chloro-4-methyl-2H-pyridazin-3-one: 1H NMR (200 MHz, CDCl3-CD3OD): 2.12 (3H, s), 3.55 (1H, brs), 7.05 (1H, s); 13C NMR (50 MHz, CDCl3): 16.1 (CH3), 131.7 (CH-5), 139.0 (C-6), 143.0 (C-4), 161.9 (C-3). 6-Chloro-5-methyl-2H-pyridazin-3-one: mp 172-173 °C (from CH2Cl2/light petrol); 1H NMR (200 MHz, CDCl3) δ 2.20 (3H, d, J = 1.3 Hz), 7.13 (1H, q, J = 1.3 Hz); 13C NMR (50 MHz, CDCl3) 16.3 (CH3), 131.9 (CH-5), 139.2 (C-4), 143.2 (C-6), 161.9 (C-3). LRMS (EI): 144 ([M+]). Anal. calcd for C5H5ClN2O: C, 41.54; H, 3.49; N, 19.38. Found: C, 41.55; H, 3.51; N, 19.22. |
46% | Stage #1: for 2 h; Reflux Stage #2: With acetic acid In water |
Intermediate VII6-Chloro-4-methyl-2H-pyridazin-3-one and 6-chloro-5-methyl-2H-pyridazin-3-one A suspension of 3,6-dichloro-4-methylpyridazine (6.60 g) in 3.3 M aqueous NaOH solution (66 mL) was stirred at reflux temperature for 2 h. The heating bath was removed and 50percent aqueous acetic acid (25 mL) was added. The aqueous solution was adjusted to pH value 6 and the precipitate formed thereafter was separated by filtration and washed with little water. The precipitate was chromatographed on silica gel (cyclohexane/ethyl acetate 90:10->0:100) to separate the two title compounds.6-Chloro-4-methyl-2H-pyridazin-3-one: Yield: 2.70 g (46percent of theory). Mass spectrum (ESI+): m/z=145/147 (Cl) [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 2.06 (d, J=1.3 Hz, 3H), 7.44 (incompletely resolved q, J=1.3 Hz, 1H), 13.03 (broad s, 1H).6-Chloro-5-methyl-2H-pyridazin-3-one: Yield: 1.90 g (32percent of theory). Mass spectrum (ESI+): m/z=145/147 (Cl) [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 2.19 (d, J=1.3 Hz, 3H), 6.91 (incompletely resolved q, J=1.3 Hz, 1H), 13.02 (broad s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | Stage #1: at 110 - 115℃; for 3 h; Stage #2: With sodium hydrogencarbonate In water |
3,6-Dichloro-4-methylpyridazine (30.6 g, 190 mmol) was suspended in glacial AcOH (800 mL) at ambient temperature and heated in an oil bath thermostatted at 110-115 °C for 3 h. (The mixture became homogenous after 1 h.) The mixture was allowed to cool and the AcOH was removed by vacuum distillation. The resulting solid residue was slowly treated with sat. NaHCO3 solution (200 mL) to give a pale yellow heterogenous mixture that was adjusted to pH 6 by the slow addition of solid NaHCO3 with vigorous stirring. The mixture was extracted with dichloromethane (2 x 250 mL) and the combined organic phase was washed with sat. NaCl solution (60 mL), dried (MgSO4) and evaporated to afford a solid (20.9 g). The crude material was subjected to column chromatography (gradient 1percent MeOH/CH2Cl2 to 5percent MeOH/CH2Cl2) to afford, 6-chloro-4-methyl-2H-pyridazin-3-one (13.4 g, 92.7 mmol; 49percent) [Rf 0.21 (2.5percent MeOH/CH2Cl2)] and 6-chloro-5-methyl-2H-pyridazin-3-one (5.00 g, 34.6 mmol; 18percent) [Rf 0.11 (2.5percent MeOH/CH2Cl2)] as a colourless solids. 6-Chloro-4-methyl-2H-pyridazin-3-one: 1H NMR (200 MHz, CDCl3-CD3OD): 2.12 (3H, s), 3.55 (1H, brs), 7.05 (1H, s); 13C NMR (50 MHz, CDCl3): 16.1 (CH3), 131.7 (CH-5), 139.0 (C-6), 143.0 (C-4), 161.9 (C-3). 6-Chloro-5-methyl-2H-pyridazin-3-one: mp 172-173 °C (from CH2Cl2/light petrol); 1H NMR (200 MHz, CDCl3) δ 2.20 (3H, d, J = 1.3 Hz), 7.13 (1H, q, J = 1.3 Hz); 13C NMR (50 MHz, CDCl3) 16.3 (CH3), 131.9 (CH-5), 139.2 (C-4), 143.2 (C-6), 161.9 (C-3). LRMS (EI): 144 ([M+]). Anal. calcd for C5H5ClN2O: C, 41.54; H, 3.49; N, 19.38. Found: C, 41.55; H, 3.51; N, 19.22. |
46% | Stage #1: for 2 h; Reflux Stage #2: With acetic acid In water |
Intermediate VII6-Chloro-4-methyl-2H-pyridazin-3-one and 6-chloro-5-methyl-2H-pyridazin-3-one A suspension of 3,6-dichloro-4-methylpyridazine (6.60 g) in 3.3 M aqueous NaOH solution (66 mL) was stirred at reflux temperature for 2 h. The heating bath was removed and 50percent aqueous acetic acid (25 mL) was added. The aqueous solution was adjusted to pH value 6 and the precipitate formed thereafter was separated by filtration and washed with little water. The precipitate was chromatographed on silica gel (cyclohexane/ethyl acetate 90:10->0:100) to separate the two title compounds.6-Chloro-4-methyl-2H-pyridazin-3-one: Yield: 2.70 g (46percent of theory). Mass spectrum (ESI+): m/z=145/147 (Cl) [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 2.06 (d, J=1.3 Hz, 3H), 7.44 (incompletely resolved q, J=1.3 Hz, 1H), 13.03 (broad s, 1H).6-Chloro-5-methyl-2H-pyridazin-3-one: Yield: 1.90 g (32percent of theory). Mass spectrum (ESI+): m/z=145/147 (Cl) [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 2.19 (d, J=1.3 Hz, 3H), 6.91 (incompletely resolved q, J=1.3 Hz, 1H), 13.02 (broad s, 1H). |
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