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CAS No. : | 22952-24-5 | MDL No. : | MFCD00110677 |
Formula : | C7H4N2O5S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HZZFBUZSKAVIOV-UHFFFAOYSA-N |
M.W : | 228.18 | Pubchem ID : | 100187 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 53.54 |
TPSA : | 117.44 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.17 cm/s |
Log Po/w (iLOGP) : | 0.2 |
Log Po/w (XLOGP3) : | 0.74 |
Log Po/w (WLOGP) : | 0.73 |
Log Po/w (MLOGP) : | -1.39 |
Log Po/w (SILICOS-IT) : | -1.58 |
Consensus Log Po/w : | -0.26 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.95 |
Solubility : | 2.55 mg/ml ; 0.0112 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.79 |
Solubility : | 0.374 mg/ml ; 0.00164 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.92 |
Solubility : | 2.72 mg/ml ; 0.0119 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.44 |
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 |
---|---|---|
72% | With chromium(VI) oxide; sulfuric acid In water at 20℃; for 24 h; | To solution chromium trioxide (20.4 g, 0.204 mol) in water (150 mL) was added concentrated sulfuric acid (190 mL) dropwise in the ice bath. 2-Methyl-5-nitrobenzenesulfonamide (10 g, 46.3 mmol) was added and the mixture was stirred at room temperature for 24 h. The mixture was filtered and the residue washed with water, dissolved in sodium bicarbonate solution and filtered under vacuum. The filtrate was acidified with concentrated HCl. After the precipitated product was filtered and washed with abundant cold water, it was dried in the vacuum-oven at 40 °C. The product was obtained a white powder in 72percent yield. Mp 205.6-205.8 °C, (lit.36 205-207 °C); IR: 3103, 1720, 1608, 1541, 1354, 1340, 1184, 1128 cm-1; 1H NMR (DMSO-d6, 300 MHz) δ/ppm: 8.02 (1H, d, J = 8.5 Hz), 8.56 (1H, d, J = 8.2 Hz), 8.71 (1H, s), 10.2 (1H, br, NH); 13C NMR (DMSO-d6, 75 MHz) δ/ppm: 117.2, 126.4, 129.8, 135.2, 143.0, 151.7, 162.2. |
71.4% | With potassium permanganate; N-benzyl-N,N,N-triethylammonium chloride In water at 95℃; for 8 h; | 2-Methyl-5-nitrobenzene sulfonamide (3, 26.1 g, 0.10 mol), benzyl triethyl ammonium chloride (TEBA) (1.2 g, 5.2 mmol) and water (250 mL) were mixed together and heated to 95 °C. The potassium permanganate (15.7 g, 0.1 mmol) was added in batches and then added water (50 mL) finally. The reaction mixture was heated to 95 °C for 8 h. The reaction residue was filtered and washed with hot water (80 mL) twice, the solution was acidified with concentrated hydrochloric acid to pH 2. A white solid was filtered off and recrystallized from ethyl alcohol to give 6-nitrosaccharin (4, 16.3 g, 71.4 percent yield), m.p.: 205.5-206.9 °C (lit. [11,12]m.p.: 212-214 °C). 1H NMR (DMSO-d6, 300 MHz) δ, ppm:7.93 (1H, d, J = 8.4 Hz), 8.41 (1H, dd, J = 1.6, 2.1 Hz), 8.47(1H, s), 10.6 (1H, br, NH). |
68% | With chromium(VI) oxide; sulfuric acid In water at 20℃; for 42 h; | Step C: 6-Nitro-l,l-dioxo-l,2-dihydro-llambda*6*-benzo[i/|isothiazol-3-oneTo a solution of Cr03 (20.8 g, 208 mmol) in water (150 mL) was slowly added concentrated sulfuric acid (190 mL). To the resulting mixture was added 2-methyl-5-nitrobenzenesulfonamide (10.0 g, 46.3 mmol) and the mixture was stirred at rt for about 42 h. The mixture was filtered and the filter cake was washed with water (100 mL). The solid was dissolved in 10percent aqueous NaHCC>3, filtered and the filtrate acidified with 2 N HC1 (pH = 1). The precipitate was collected by filtration and washed with water (2 x 50 mL) to provide 6-nitro-l,l-dioxo-l,2-dihydro- llambda*6*-benzo[i/]isothiazol-3-one (7.2 g, 68percent). .H NMR (DMSO- ) δ: 8.42-8.53 (m, 2H), 8.00 (s, 1H), 3.70 (br s, 1H). |
55% | With chromium(VI) oxide; sulfuric acid In water at 20℃; for 24 h; | 5.1.1 6-Nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide (4) To a solution of chromium trioxide (9.0 g, 900 mmol) in water (67 ml), concentrated sulfuric acid (83.5 ml) was added gradually. The mixture was added 2-methyl-5-nitrobenzenesulfonamide 3 (4.32 g, 20 mmol) and then stirred at room temperature for 24 h. Crude product was obtained by filtration and then washed with water. The filter cake was stirred in 10percent sodium bicarbonate solution and the insoluble residue was removed by filtration. The filtrate was acidified with 5percent hydrochloric acid solution to generate the purified product with 55percent yield, mp: 203-205 °C. 1H NMR (DMSO-d6) δ 7.91 (d, J = 8.4 Hz, 1H), 8.47 (dd, J = 7.8 Hz, 1.8 Hz, 1H), 8.54 (s, 1H). MS (ESI) m/z: 227.1 [M-H]-. |
A851474[ 2665661-12-9 ]
Ammonium 6-nitro-3-oxo-3H-benzo[d]isothiazol-2-ide 1,1-dioxide
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