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CAS No. : | 51175-71-4 | MDL No. : | MFCD02682011 |
Formula : | C4H3ClO2S2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YSPWSQNKRBSICH-UHFFFAOYSA-N |
M.W : | 182.65 | Pubchem ID : | 2776378 |
Synonyms : |
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Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 3261 |
Hazard Statements: | H314 | 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 |
---|---|---|
22% | B. N-(4-Bromo-3-methyl-5-isoxazolyl)thiophene-3-sulfonamide N-(4-Bromo-3-methyl-5-isoxazolyl)thiophene-3-sulfonamide was prepared in the same manner as described in Example 2 from thiophene-3-sulfonyl chloride with <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> in 22% yield. Purification by column chromatography using 10% MeOH/CHCl3 as eluent gave a pale brown oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 78 Synthesis of 3-[5-Methoxy-1-(thiophene-3-sulfonyl)-1H-indol-3-yl]-propionic acid 99 3-[5-Methoxy-1-(thiophene-3-sulfonyl)-1H-indol-3-yl]-propionic acid 99 was prepared from <strong>[39547-16-5]3-(5-methoxy-1H-indol-3-yl)-propionic acid</strong> 96 and 3-thienyl-sulfonyl chloride using the same protocol as described in step 8, Example 4. (M-1, 364.4) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | B. N-(4-Bromo-3-methyl-5-isoxazolyl)thiophene-3-sulfonamide N-(4-Bromo-3-methyl-5-isoxazolyl)thiophene-3-sulfonamide was prepared in the same manner as described in Example 2 from thiophene-3-sulfonyl chloride with 5-amino-4-bromo-3-methylisoxazole in 22% yield. Purification by column chromatography using 10% MeOH/CHCl3 as eluent gave a pale brown oil. | |
22% | B. N-(4-Bromo-3-methyl-5-isoxazolyl)thiophene-3-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)thiophene-3-sulfonamide was prepared in the same manner as described in Example 2 from thiophene-3-sulfonyl chloride with 5-amino-4-bromo-3-methylisoxazole in 22% yield. Purification by column chromatography using 10% MeOH/CHCl3 as eluent gave a pale brown oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 0 - 20℃; for 6h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | A 50 ml Schlenk flask was charged with a magnetic stirrer bar and 95% NaH (365 mg, 15.2 mmol, 1.02 equiv) under a nitrogen atmosphere (glove box). The flask was capped with a rubber septum, then 10 ml of dry THF was added. The resulting slurry was cooled to 0 C. and a solution of <strong>[19228-91-2]tert-butyl thiophen-3-ylcarbamate</strong> (2) (3000 mg, 15 mmol, 1 equiv) in 10 ml of dry THF was added to the mixture via a syringe for 5 minutes. After the addition was complete, the mixture was allowed to warm up to room temperature and was stirred at room temperature for 1 hour. Then, the reaction mixture was cooled down again to 0 C. and a solution of thiophene-3-sulfonyl chloride (3) (2748 mg, 15 mmol, 1 equiv) in 10 ml of dry THF was added via a syringe for 10 minutes. After the addition was complete, the cooling bath was removed and the reaction mixture was stirred at room temperature overnight. After that, the mixture was poured into an excess of ammonium chloride and extracted with dichloromethane (2×100 ml). The combined organic layers were washed with water and brine and dried over -Na2SO4. The solvent was removed under reduced pressure and the residue was recrystallized from -iPrOH affording the product 4 (4657 mg, 13.5 mmol) as a light yellow solid at 90% yield. 1H NMR (499 MHz, -CDCl3) delta 8.12 (dd, J=3.1, 1.3 Hz, 1H), 7.45 (dd, J=5.2, 1.3 Hz, 1H), 7.41 (dd, J=5.2, 3.1 Hz, 1H), 7.30 (dd, J=5.1, 3.2 Hz, 1H), 7.23 (dd, J=3.2, 1.4 Hz, 1H) 1.38 (s, 9H). 13C NMR (-CDCl3) delta 150.59, 138.66, 133.17, 133.01, 127.18, 127.15, 126.41, 124.93, 124.36, 84.65, 27.82. HRMS (ESI-TOF) m/z: -[M+Na]+ Calcd. for -C13H15NNaO4S3 368.0054. Found 368.0055. | |
In tetrahydrofuran; | Step 1-Preparation of tert-butyl thiophen-3-yl(thiophen-3-ylsulfonyl)carbamate (4) A 50 ml Schlenk flask was charged with a magnetic stirrer bar and 95% NaH (365 mg, 15.2 mmol, 1.02 equiv) under a nitrogen atmosphere (glove box). The flask was capped with a rubber septum, then 10 ml of dry THF was added. The resulting slurry was cooled to 0 C. and a solution of <strong>[19228-91-2]tert-butyl thiophen-3-ylcarbamate</strong> (2) (3000 mg, 15 mmol, 1 equiv) in 10 ml of dry THF was added to the mixture via a syringe for 5 minutes. After the addition was complete, the mixture was allowed to warm up to room temperature and was stirred at room temperature for 1 hour. Then, the reaction mixture was cooled down again to 0 C. and a solution of thiophene-3-sulfonyl chloride (3) (2748 mg, 15 mmol, 1 equiv) in 10 ml of dry THF was added via a syringe for 10 minutes. After the addition was complete, the cooling bath was removed and the reaction mixture was stirred at room temperature overnight. After that, the mixture was poured into an excess of ammonium chloride and extracted with dichloromethane (2*100 ml). The combined organic layers were washed with water and brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was recrystallized from iPrOH affording the product 4 (4657 mg, 13.5 mmol) as a light yellow solid at 90% yield. 1H NMR (499 MHz, CDCl3) delta 8.12 (dd, J=3.1, 1.3 Hz, 1H), 7.45 (dd, J=5.2, 1.3 Hz, 1H), 7.41 (dd, J=5.2, 3.1 Hz, 1H), 7.30 (dd, J=5.1, 3.2 Hz, 1H), 7.23 (dd, J=3.2, 1.4 Hz, 1H) 1.38 (s, 9H). |