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CAS No. : | 943606-83-5 | MDL No. : | MFCD27933966 |
Formula : | C10H8N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SJCNLOPXPBCMGQ-UHFFFAOYSA-N |
M.W : | 204.18 | Pubchem ID : | 67341016 |
Synonyms : |
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Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P201-P202-P281-P308+P313-P405-P501 | UN#: | 2811 |
Hazard Statements: | H350 | 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 |
---|---|---|
99% | With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; | 2.3 Preparation of 6-methyl-5-nitroisoquinolin-2-oxide 6-methyl-5-nitroisoquinoline (43.3 g, 0.230 mol) obtained in above was dissolved in dichloromethane (650 mL), and the reaction solution was cooled to 0°C or below. Subsequently, mCPBA (67.5 g, 0.390 mol) was slowly added to the reaction solution, followed by stirring for 10 hours or more at 0°C. The reaction mixture was adjusted to pH 10 by adding 1 N NaOH solution, and subjected to extraction with dichloromethane. The obtained organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (46.5 g, 99%). 1H-NMR Spectrum (300 MHz, CDC13): δ 8.80 (s, 1H), 8.24 (d, 1H), 7.80 (d, 1H), 7.66 (d, 1H), 7.56 (d, 1H), 2.55 (s, 3H) |
99% | With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; | 2.3 Preparation of 6-methyl-5-nitroisoquinolin-2-oxide 6-methyl-5-nitroisoquinoline (43.3 g, 0.230 mol) obtained in above was dissolved in dichloromethane (650 mL), and the reaction solution was cooled to 0° C. or below. Subsequently, mCPBA (67.5 g, 0.390 mol) was slowly added to the reaction solution, followed by stirring for 10 hours or more at 0° C. The reaction mixture was adjusted to pH 10 by adding 1 N NaOH solution, and subjected to extraction with dichloromethane. The obtained organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (46.5 g, 99%). 1H-NMR Spectrum (300 MHz, CDCl3): δ 8.80 (s, 1H), 8.24 (d, 1H), 7.80 (d, 1H), 7.66 (d, 1H), 7.56 (d, 1H), 2.55 (s, 3H) |
99% | With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 10h; | 2.3 Preparation of 6-methyl-5-nitroisoquinoline-2-oxide 6-Methyl-5-nitroisoquinoline (43.3 g, 0.230 mol) obtained in Step (2) above was dissolved in dichloromethane (650 mL), and the temperature of the reaction solution was cooled to 0°C or lower. The reaction solution was slowly added with mCPBA (67.5 g, 0.390 mol), followed by stirring for 10 hours or more at 0°C. The reaction mixture was adjusted to have a pH value of 10 by adding 1N aqueous NaOH solution and extracted with dichloromethane. The combined organic layer thus obtained was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (46.5 g, 99 %). 1H-NMR Spectrum (300 MHz, CDCl3): δ 8.80(s, 1H), 8.24(d, 1H), 7.80(d, 1H), 7.66(d, 1H), 7.56(d, 1H), 2.55(s, 3H) |
99% | With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; | 2.3 Step (3):Preparation of 6-methyl-5-nitroisoquinoline-2-oxide 6-Methyl-5-nitroisoquinoline (43.3 g, 0.230 mol) obtained in Step (2) above was dissolved in dichloromethane (650 mL), and the temperature of the reaction solution was cooled to 0° C. or lower. The reaction solution was slowly added with mCPBA (67.5 g, 0.390 mol), followed by stirring for 10 hours or more at 0° C. The reaction mixture was adjusted to have a pH value of 10 by adding 1N aqueous NaOH solution and extracted with dichloromethane. The combined organic layer thus obtained was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (46.5 g, 99%). 1H-NMR Spectrum (300 MHz, CDCl3): δ 8.80 (s, 1H), 8.24 (d, 1H), 7.80 (d, 1H), 7.66 (d, 1H), 7.56 (d, 1H), 2.55 (s, 3H) |
76% | Stage #1: 6-methyl-5-nitroisoquinoline With potassium peroxymonosulfate sulfate In water at 50 - 60℃; for 15h; Industrial scale; Stage #2: With sulfuric acid In water at 70 - 80℃; for 1h; Industrial scale; | |
75% | With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 2 - 20℃; | 2 Example 2 Preparation of 6-methyl-5-nitroisoquinoIine-N-oxide6-Methyl-5-nitroisoquinoline (100.0 g, 531 mmol) in Dichlormethane (1 L) was added to a 2 L 3-necked round bottomed flask and cooled to 5 0C. Purified m-chloroperoxobenzoic acid (129 g, 749 mmol) was added to this stirred solution [m-CPBA was extracted with saturated Phosphate buffer pH 7.5 and DCM]. Initially with the addition of mCPBA the reaction exothermed, but then endothermed to 2 0C. After 20 min, the contents in the flask solidified to a yellow/white solid and more DCM (300 mL) was added. The reaction was allowed to stir overnight at room temperature. DCM (2 L) was added and the mixture washed with 1 N NaOH (1 L), saturated sodium bicarbonate (1 L) and brine (1 L).The solution was dried over sodium sulfate and concentrated to give 6-methyl-5- nitroisoquinoline-N-oxide (81.7 g, 75%). MS (M+H)4" 205. |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 4h; | ||
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 4h; | 2 6-Methyl-5-nitroisoquinoline (32 g, 170 mmol) was dissolved in DCM (500 mL) and cooled in an ice-acetone bath to 0 0C. 3-Chloroperoxybenzoic acid (49.9 g, 289 mmol) (73%) was added in portions while stirring the reaction mixture vigorously. After the addition, the reaction mixture was stirred at 0 0C for 4 h. Upon being warmed to RT, the reaction mixture was partitioned in DCM/NaOH (aq., 1 N). After multiple extractions, the organic layers were combined and washed with brine then dried over Na2SO4. Removal of the solvent in vacuo gave 6-methyl-5-nitroisoquinoline N-oxide as a yellow solid (23 g). MS (M+H)+ 205. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: trichlorophosphate; lithium chloride / N,N-dimethyl-formamide; dichloromethane / 17 h / 35 - 45 °C / Large scale 2.1: triethylamine / 5 h / 105 °C 3.1: ammonium hydroxide / 2-methyltetrahydrofuran / 3 h / 25 °C / Inert atmosphere; Large scale 3.2: 34 h / 50 °C / 2175.22 Torr / Large scale 4.1: N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; 2,6-dimethylpyridine / tetrahydrofuran / 6 h / 40 °C / Inert atmosphere |