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CAS No. : | 111248-89-6 | MDL No. : | MFCD11043148 |
Formula : | C7H7NO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OJWMDOIYUCEXNF-UHFFFAOYSA-N |
M.W : | 169.20 | Pubchem ID : | 15536009 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 45.69 |
TPSA : | 54.55 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) : | -7.01 cm/s |
Log Po/w (iLOGP) : | 0.86 |
Log Po/w (XLOGP3) : | 0.46 |
Log Po/w (WLOGP) : | 1.3 |
Log Po/w (MLOGP) : | 0.24 |
Log Po/w (SILICOS-IT) : | 0.89 |
Consensus Log Po/w : | 0.75 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.58 |
Solubility : | 4.43 mg/ml ; 0.0262 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.17 |
Solubility : | 11.3 mg/ml ; 0.067 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.64 |
Solubility : | 0.388 mg/ml ; 0.00229 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.39 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-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 |
---|---|---|
80% | With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; tert-butyl XPhos In tetrahydrofuran at 80℃; for 13 h; Microwave irradiation | (2-Chlorophenyl)methanesulfonamide (450 mg, 2.19 mmol), tris(dibenzylideneacetone) dipalladium (100 mg, 0.109 mmol), 2-di-tert-butylphosphino-2',4',6'-tri-isopropylbiphenyl (186 mg, 0.438 mmol) and potassium carbonate (605 mg, 4.38 mmol) were loaded in a microwave vial and THF (8.8 mL) was added. The reaction mixture was stirred at 80 °C for 13 h before being quenched with a saturated solution of ammonium chloride. The solvent was then evaporated and the residue was purified by column chromatography (cyclohexane/acetone) to afford the title compound as a white solid (296 mg, 80percent). 1H NMR (500 MHz, CDCl3) ppm = 7.31 - 7.26 (m, 1 H), 7.26 - 7.23 (m, 1 H), 7.07 (td, J=7.6, 0.9, 1 H), 6.90 (d, J=8.0, 1 H), 6.48 (bs, 1 H), 4.39 (s, 2H). Rt = 1.69 min (HPLC method C). |
80% | With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; tert-butyl XPhos In tetrahydrofuran at 80℃; for 13 h; | 4b. I ,3-Dihydrobenzo[c]isothiazole 2,2-dioxide (2-Chlorophenyl)methanesulfonamide (450 mg, 2.19 mmol),tris(dibenzylideneacetone) dipalladium (100 mg, 0.109 mmol), 2-di-tert butylphosphino-2’,4’,6’-tri-isopropylbiphenyl (186 mg, 0.438 mmol) and potassium carbonate (605 mg, 4.38 mmol) were loaded in a microwave vial and THF (8.8 mL) wasadded. The reaction mixture was stirred at 80 °C for 13 hr before being quenched with a sat. NH4CI solution. The solvent was then evaporated and the residue was purified by column chromatography (CyHex/acetone) to afford the title compound as a white solid (296 mg, 80percent). 1H NMR (500 MHz, CDCI3) ppm = 7.31 - 7.26 (m, 1H), 7.26 - 7.23 (m, 1H), 7.07 (td, J=7.6, 0.9, IH), 6.90 (d, J=8.0, IH), 6.48 (bs, IH), 4.39 (s, 2H); Rt = 1.69mm (HPLC method F). |
80% | With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; tert-butyl XPhos In tetrahydrofuran at 80℃; for 13 h; | b. 1,3-Dihydrobenzo[c]isothiazole 2,2-dioxide (2-Chlorophenyl)methanesulfonamide (450 mg, 2.19 mmol), tris(dibenzylideneacetone)dipalladium (100 mg, 0.109 mmol), 2-di-tert-butylphosphino-2',4',6'-tri-isopropylbiphenyl (186 mg, 0.438 mmol) and potassium carbonate (605 mg, 4.38 mmol) were loaded in a microwave vial and THF (8.8 mL) was added. The reaction mixture was stirred at 80° C. for 13 h before being quenched with a sat. NH4Cl solution. The solvent was then evaporated and the residue was purified by column chromatography (CyHex/acetone) to afford the title compound as a white solid (296 mg, 80percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.5% | Stage #1: With tin(ll) chloride In ethyl acetate at 70℃; Stage #2: With triethylamine In dichloromethane at 20℃; |
Preparation 17 1,3-Dihydrobenzo[c]isothiazole 2,2-dioxide The title compound was prepared using the method described in WO 98/32438 A1. To a solution of 2-nitro-alpha-toluenesulfonyl chloride (5.1 g, 21.6 mmol) in anhydrous ethyl acetate (250 mL) was added tin(II) chloride (19.3 g, 86 mmol). The reaction was stirred overnight at 70° C., then poured onto ice and neutralized with saturated aqueous sodium bicarbonate. The solution was filtered through Celite, extracted with ethyl acetate, and the organic layer concentrated. To the crude residue was added anhydrous methylene chloride (200 mL) and triethylamine (5 mL). The solution was stirred overnight at room temperature and concentrated under reduced pressure. The product was obtained by silica gel column chromatography (30-100percent ethyl acetate in hexanes) followed by recrystallization from methylene chloride/hexanes to give a white solid. (0.24 g, 6.5percent). 1H NMR (CDCl3, 300 MHz) δ 7.30-7.22 (m, 2H), 7.07-7.02 (t, 1H, J=7.4 Hz), 6.89-6.86 (dd, 1H, J=0.6, 8.1 Hz), 6.66 (br s, 1H), 4.39 (s, 1H). |
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