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CAS No. : | 6162-21-6 | MDL No. : | MFCD18825611 |
Formula : | C8H12N2O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VNUVBVTWBBODSV-UHFFFAOYSA-N |
M.W : | 200.26 | Pubchem ID : | 14026341 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 51.64 |
TPSA : | 71.78 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) : | -6.98 cm/s |
Log Po/w (iLOGP) : | 1.3 |
Log Po/w (XLOGP3) : | 0.76 |
Log Po/w (WLOGP) : | 1.48 |
Log Po/w (MLOGP) : | 0.38 |
Log Po/w (SILICOS-IT) : | -0.48 |
Consensus Log Po/w : | 0.69 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.77 |
Solubility : | 3.4 mg/ml ; 0.017 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.85 |
Solubility : | 2.85 mg/ml ; 0.0142 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.08 |
Solubility : | 1.67 mg/ml ; 0.00834 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.73 |
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 |
---|---|---|
64% | With ammonium nitrate; sulfuric acid; In water; at 0℃; for 0.25h; | General procedure: NH4NO3 (1.1 equiv) was added portion wise to a solution of aromaticsulfonamides A-H (1.2 mmol, 1.0 equiv) in 95% H2SO4 (1 ml)at 0 C. The suspension was stirred at the same temperature for15 min, then quenched with slush (8 ml) and the formed precipitatewas filtered-off and washed with cold water. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With hydrogenchloride; In N,N-dimethyl-formamide; | EXAMPLE 2 Preparation of 4-N',N'-dimethylamino-N-(5-chloro-2-quinoxalinyl)benzenesulfonamide A suspension of sodium hydride (60%, 114 mg, 2.85 mmol) in N,N-dimethylformamide (10 ml) under nitrogen at room temperature was treated with p-dimethylaminobenzenesulfonamide (214 mg, 1.07 mmol), and after stirring one hour, solid <strong>[55687-05-3]2,5-dichloroquinoxaline</strong> (231 mg, 1.16 mmol) was added. After stirring overnight, the reaction mixture was poured into water (100 ml) and the pH adjusted to 3-4 by the addition of 1N hydrochloric acid solution. The resulting precipitate was collected, dried and purified by silica gel flash chromatography (EtOAc/hexanes/THF) to yield the title product (56 mg, 14%) as a solid. Analysis of the title compound gave the following results: 1 H NMR (300 MHz, d6 -DMSO)delta2.92(s, 6H, CH3), 6.72 (d, 2H, J=7.8 Hz, Ar-H), 7.68-7.84 (overlapping multiplets, 3H, Ar-H), 7.85 (d, 2H, J=8.0 Hz, Ar-H), 8.61 (s, 1H, Ar-H), 11.78(s, 1H, exchanges with D2 O, NH); IR(KBr) 1600, 1582, 3.448, 1148 and 1089 cm-1; FDMS(DMSO) m/e=362, 364 (M+). Analysis of C16 H15 ClN4 O2 S: Theory: C, 52.96; H, 4.17; N, 15.44. Found: C, 53.17; H, 4.30; N, 15.30. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | In N,N-dimethyl-formamide; | EXAMPLE 1 Preparation of 4-N',N'-dimethylamino-N-(6,7-dichloro-2-quinoxalinyl)benzenesulfonamide A suspension of sodium hydride (60%, 160 mg, 4.0 mmol) in N,N-dimethylformamide (10 ml) under a nitrogen atmosphere at room temperature was treated with <strong>[6162-21-6]p-dimethylaminobenzenesulfonamide</strong> (300 mg, 1.5 mmol), and after stirring one hour, solid 2,6,7-trichloroquinoxaline (308 mg, 1.33 mmol) was added. After five hours, additional 2,6,7-trichloroquinoxaline (45 mg, 0.20 mmol) was added and stirring continued overnight. The reaction mixture was carefully poured into excess pH 4.0 buffer and extracted with ethyl acetate (3X). The combined extract was washed with water, brine and dried over sodium sulfate. Filtration and evaporation yielded a solid which was purified by silica gel flash chromatography (EtOAc/hexanes) to yield the title product (100 mg, 19%) as a solid. Analysis of the title compound gave the following results: 1 H NMR (300 MHz, d6 -DMSO)delta2.94(s, 6H, CH3), 6.74, (d, 2H, J=9.1 Hz, Ar-H), 7.87 d, 2H, J=9.0 Hz, Ar-H), 8.07 (s, 1H, Ar-H), 8.20 (s, 1H, Ar-H), 8.52 (s, 1H, Ar-H), 11.82 (s, 1H, exchanges with D2 O, NH); IR(KBr) 3114, 3057, 1601, 1383, 1316 and 1154 cm-1; UV(EtOH)lambdamax(epsilon) 216.0(41035), 254.4(29214), 283.2(23127) and 350.2 (8436) nm; FDMS(DMSO) m/e=396, 398, 400 (M+). Analysis of C16 H14 Cl2 N4 O2 S: Theory: C, 48.37; H, 3.55; N, 14.10. Found: C, 48.16; H, 3.56; N, 13.92. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | General procedure: A suspension of potassium hydride (3 equiv) in THF (0.6 M) was cooled in an ice-water bath. A solution of sulfonamide, sulfonamide or aniline (1.0 equiv) in THF (0.20 M) was added dropwise, and the suspension was stirred for 15 min. 1,1'-Carbonyldiimidazole (1.0 equiv) was dissolved in 1:1 THF/dioxane (0.20 M) and added dropwise to the reaction mixture, resulting in the formation of a white precipitate. The ice-water bath was removed, and the reaction mixture was allowed to warm to ambient temperature and was stirred for 2 h. A solution of diamine S-1 (1.0 equiv) in THF (1.0 M) was added dropwise, and the suspension was stirred at room temperature for 20 h. The reaction was quenched with a solution of acetic acid (3 equiv) in THF (1.0 M). The crude product was concentrated in vacuo and purified by silica gel chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | N-(4-chloro-2-nitrophenyl)-<strong>[6162-21-6]4-(dimethylamino)benzenesulfonamide</strong> A solution of <strong>[6162-21-6]4-(dimethylamino)benzenesulfonamide</strong> (CAS 6162-21-6) (1 equiv.) in DMF was cannulated into NaH in DMF at room temperature. After stirring for 10 min, 4-chloro-1-fluoro-2-nitrobenzene (1 equiv) in DMF was added into the above solution and stirred for another 30 min. The reaction was quenched with water and extracted with EtOAc (*2). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated. The crude product was purified by flash column chromatography on silica gel to yield Intermediate 7 as an orange solid (45% yield). 1H NMR (300 MHz, CD3OD) delta ppm 8.20 (d, J=1.47 Hz, 1H), 7.77 (d, J=9.08 Hz, 2H), 7.54 (d, J=2.93 Hz, 2H), 7.46 (d, 2H), 2.65-2.74 (m, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; for 1h; | Iodomethane (2.0 equiv) was added dropwise to a suspension ofsulfanilamide C (0.5 g, 1.0 equiv) and potassium carbonate(2.0 equiv) in dry DMF (2 ml). The mixture was stirred at 50 Cfor 1 h, then cooled and quenched with H2O (20 ml) and theformed precipitate was filtered-off, washed with H2O and recrystallizedfrom acetone to afford the titled compound D as a whitesolid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With potassium acetate; copper(II) acetate monohydrate In nitrobenzene at 200℃; for 15h; |
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