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CAS No. : | 16024-82-1 | MDL No. : | MFCD00041062 |
Formula : | C9H7NO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UNXVHBOJSCWVCD-UHFFFAOYSA-N |
M.W : | 193.22 | Pubchem ID : | 85243 |
Synonyms : |
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Signal Word: | Danger | Class: | 8,6.1 |
Precautionary Statements: | P260-P264-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P311-P321-P363-P403+P233-P405-P501 | UN#: | 2922 |
Hazard Statements: | H314-H331-H302+H312 | Packing Group: | Ⅲ |
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 |
---|---|---|
In diethyl ether for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With triethylamine In 1,4-dioxane for 10h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / toluene / 4 h / Heating 2: dimethylformamide / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 57 percent / SnCl4 / 16 h / 20 °C 2: 100 percent / hydrazine / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 79 percent / 16 h / Heating 2: 100 percent / hydrazine / ethanol / 3 h / Heating | ||
Multi-step reaction with 3 steps 1: 79 percent / 16 h / Heating 2: 93 percent / hydrazine / ethanol / 96 h / Ambient temperature 3: 53 percent / hydrazine / ethanol / 2.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With triethylamine; In methanol; at 20℃; for 20h; | EXAMPLE A1; 1'-[4-(4-methylpiperazin-1-yl)benzyl]-2'H-spiro[cyclopentane-1,3'-imidazo[2,1-b]quinazoline]-2',5'(1'H)-dione hydrochloride Stage 1: methyl 1-(4-oxo-2-thioxo-1,4-dihydroquinazolin-3(2H)-yl) cyclopentane carboxylateA mixture of <strong>[60421-23-0]methyl 1-aminocyclopentanecarboxylate hydrochloride</strong> (1 g), methyl 2-isothiocyanatobenzoate (1.18 g) and triethylamine (15 mL) in methanol (60 ml) is stirred at ambient temperature for 20 hours then concentrated under reduced pressure at 40 C. Dichloromethane and water are added to the solid obtained. After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40 C. Purification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 7:3 to 6:4) produces the expected compound in the form of powder (1.08 g, 64% yield).MS/LC: calculated MM=304.4; m/z=305.2 (MH+)NMR (1H, 400 MHz, DMSO-d6): delta 1.76-1.95 (m, 6H), 2.07 (m, 2H), 3.73 (s, 3H), 7.42 (AB, 1H), 7.60 (m, 1H), 7.74 (m, 1H), 7.99 (AB, 1H), 10.8 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With triethylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In ethanol; at 20℃; for 5.0h; | A mixtureof compound 2 (1.93 g, 0.01 mole) and 4-amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide (3.14 g, 0.01 mole) in absolute ethanol (30 mL) was stirred at room temperature for 5 h. The reaction mixture was poured onto ice water and the solid obtained was recrystallized from dioxane to give 3. Yield% 88; m.p. 322.9 C; IR (KBr, nmax, Cm-1): 3448, 3275(NH),3039 (CH arom.), 2977, 2863 (CH aliph.), 1662 (C=O), 1620(C=N), 1342, 1168 (SO2), 1261 (C=S). 1H NMR spectrum in(DMSO-d6): 4.21 [s, 3H, OCH3], 6.60, 7.64 [2d, 2H, 2CHpyrazole, J = 7.33 Hz], 7.08- 8.12 [m, 13H, Ar-H], 11.46 [s,1H, SO2NH, D2O-exchangeable], 12.95 [s, 2H, 2NH, D2O exchangeable].13C NMR spectrum (in DMSO-d6): 52.4, 95.6,121.3 (2), 121.8, 127.9 (2), 128.5 (2), 129.0 (2), 131.4, 132.6,134.3, 137.8, 139.6, 141.2, 141.8, 144.9, 168.1, 181.2. Anal.Calc. for C24H21N5O4S2 (508): C, 56.79; H, 4.17; N, 13.80;found: C, 56.42; H, 4.34; N, 13.49. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With triethylamine; In ethanol; for 18.0h;Reflux; | A mixture of compound 2 (1.93 g, 0.01 mole) and 4-amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide (3.14 g, 0.01 mole) in absolute ethanol (30 mL) containing a catalytic amount of triethylamine was refluxed for 18 h. The reaction mixture was cooled and poured onto ice water and the solid obtained was recrystallized from dioxane to give 4. Yield % 90; m.p. 300.4 C; IR (KBr, nmax, Cm-1): 3307, 3210(NH), 3088 (CH arom.), 1688 (C=O), 1610 (C=N), 1365, 1155(SO2), 1272 (C=S). 1H NMR spectrum (in DMSO-d6): 6.44,7.41 [2d, 2H, 2CH pyrazole, J = 6.97 Hz], 7.05-8.23 [m, 13H,Ar-H], 9.35 [s, 1H, NH, D2O-exchangeable], 11.44 [s, 1H,SO2NH, D2O-exchangeable]. 13C NMR spectrum (in DMSOd6):91.7, 119.8 (2), 120.6 (2), 122.7, 124.6, 125.1, 126.8 (2),127.6, 127.9, 128.5 (2), 130.6, 134.1, 134.7, 140.4, 141.3,141.9, 144.8, 162.7, 187.3. Anal. Calc. for C23H17N5O3S2 (476):C, 58.09; H, 3.60; N, 14.73; found: C, 58.32; H, 3.31; N, 14.51. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With triethylamine In ethanol for 15h; Reflux; | Synthesis of N-(2,6-dimethoxypyrimidin-4-yl)-4-(4-oxo-2-thioxo-1,2-dihydro-quinazolin-3(4H)-yl)benzenesulfonamide (5) A mixture of compound 2 (1.93 g, 0.01 mole) and 4-amino-N-(3,5-dimethoxy-phenyl)benzenesulfonamide (3.08 g, 0.01 mole) in absolute ethanol (30 mL) containing a catalytic amount of triethylamine was refluxed for 15 h. The reaction mixture was cooled and poured onto ice water and the solid obtained was recrystallized from DMF/ EtOH to give 5. Yield % 84; m.p. 219.1 °C; IR (KBr, nmax, Cm-1): 3216, 3194(NH), 3065 (CH arom.), 1691 (C=O), 1622 (C=N), 1357, 1163(SO2), 1265 (C=S). 1H NMR spectrum (in DMSO-d6): 3.62,3.74 [2s, 6H, 2OCH3], 6.26 [s, 1H, CH pyrimidine], 7.13-8.28[m, 8H, Ar-H], 8.93 [s, 1H, NH, D2O-exchangeable], 10.90[s, 1H, SO2NH, D2O-exchangeable]. 13C NMR spectrum (inDMSO-d6): 56.6 (2), 84.3, 120.8 (2), 122.6, 125.7, 126.3 (2),126.9, 127.8, 129.8, 134.6, 134.9, 138.4, 161.3, 161.7, 163.2,174.1, 187.8. Anal. Calc. for C20H17N5O5S2 (472): C, 50. 95;H, 3.63; N, 14.85; found: C, 50.66; H, 3.29; N, 14.49. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With triethylamine In 1,4-dioxane at 20℃; for 2h; | 3-Phenyl-2-thioxoquinazoline-4-one (10a) General procedure: To a solution of methyl 2-isothiocyanatobenzoate (46.7 mg, 0.242 mmol) and aniline (22.1 μL, 0.242 mmol) in 1,4-dioxane (2.0 mL) was added Et3N (37.4 μL, 0.242 mmol). The mixture was stirred at r.t. for 2 h, and the precipitated white solid was collected by filtration, washed with n-hexane, and recrystallized from CHCl3 and n-hexane to afford the title compound (47.0 mg, 0.185 mmol, 76%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | With triethylamine; In 1,4-dioxane; at 20℃; for 10h; | To a solution of methyl 2-isothiocyanatobenzoate (98.8 mg, 0.511 mmol) and 14b (74.0 mg, 0.499 mmol) in dioxane(2.0 mL) was added Et3N (80 muL, mmol). The mixture was stirred at r.t. for 10 h, and the precipitated white solid was collected by filtration and washed with n-hexane to give the title compound (18.9 mg, 0.0818 mmol, 16%) as a white solid. mp>300C. 1H-NMR (500 MHz, DMSO-d6) delta: 7.98 (1H, dd, J=1.2, 8.0 Hz), 7.88 (1H, d, J=8.1 Hz), 7.83-7.80 (1H, m), 7.47 (1H, d, J=8.0 Hz), 7.39-7.36 (2H, m), 7.12 (1H, dd, J=1.7, 8.0 Hz), 3.89 (3H, s). 13C-NMR (125 MHz, DMSO-d6) delta: 175.30, 161.55, 159.60, 145.42, 139.87, 135.73, 133.91, 127.33, 124.40, 122.48, 116.24, 116.09, 115.94, 113.78, 99.97, 56.63. FAB-MS m/z 310 (MH+). Anal. Calcd for C16H11N3O2S: C, 62.12; H, 3.58; N, 13.58. Found: C, 61.98; H, 3.66; N, 13.47 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Stage #1: methyl 2-isothiocyanatobenzoate; 3-amino-4-hydroxytoluene With potassium carbonate In dimethyl sulfoxide at 25℃; for 0.5h; Green chemistry; Stage #2: With potassium metaperiodate In water; dimethyl sulfoxide at 80℃; Green chemistry; | Fused Tetracyclic Quinazolinones 7; General Procedure General procedure: Following the above described general procedure for the synthesis of benzazoles, methyl 2-isothiocyanatobenzoate (2m; 0.0521 g, 0.27mmol) was reacted with amino derivative 1. After completion of thereaction, the mixture was treated with CH2Cl2 (2 mL). The resulting precipitate was filtered, washed with CH2Cl2, and oven-dried at 80 °C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With sulfur; triethylamine In N,N-dimethyl-formamide at 50℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With sulfur; triethylamine In N,N-dimethyl-formamide at 50℃; |