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CAS No. : | 6452-57-9 | MDL No. : | MFCD00128146 |
Formula : | C6H15NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 133.19 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P261-P273-P280-P305+P351+P338-P310 | UN#: | 2735 |
Hazard Statements: | H314-H332-H335-H412 | Packing Group: | Ⅲ |
GHS Pictogram: |
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* 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 |
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62% | With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
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With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
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With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
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With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
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With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
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With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
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With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
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With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
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With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
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6% | With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol for 3h; Ambient temperature; | ||
In isopropyl alcohol 1.) 70 deg C, 1.5 h, 2.) RT, 15 h; | ||
53 g | at 25℃; |
I.a 3-(Isopropylamino)-1,2-propanediol 3-(Isopropylamino)-1,2-propanediol A mixture of 37 g (0.5 mole) of glycidol and 35.4 g (0.6 mole) of isopropylamine was stirred at 25° C. overnight. Excess isopropylamine was evaporated in vacuo and the mixture was distilled to give 53 g of product: b.p. 80° C./0.1 mm Hg. The NMR and IR spectra were consistent with the assigned structure and the elemental analysis was consistent with the empirical formula C6 H15 O2 N. | ||
XIV 3-(Isopropylamino)-1,2-propanediol 3-(Isopropylamino)-1,2-propanediol A mixture of 37 g (0.5 mole) of glycidol and 35.4 g (0.6 mole) of isopropylamine was stirred at 25° overnight. Excess isopropylamine was evaporated in vacuo and the mixture was distilled to give 53 g of product: b.p. 80° C./0.1 mm Hg. The NMR and IR spectra were consistent with the assigned structure and the elemental analysis was consistent with the empirical formula C6 H15 O2 N. | ||
In ethanol at 20℃; for 5h; | 146.A Part A: 3-(isopropylamino)propane-1,2-diol To propan-2-amine (0.399 g, 6.75 mmol) in ethanol (2 mL) was added oxiran- 2-ylmethanol (0.5 g, 6.75 mmol) slowly. The mixture was stirred at room temperature for 5 h. The crude reaction mixture was concentrated under reduced pressure to afford 3-(isopropylamino)propane-l,2-diol (0.82 g, 6.16 mmol, 91 % crude yield) as a brownish color semi-solid which was carried forward without further purification. LC/MS (ESI) m/e 133.9 [(M+H)+, calcd for C6Hi6N02 134.2]; 1H NMR (400MHz, CDC13) δ 3.76 - 3.49 (m, 3H), 2.89 - 2.60 (m, 3H), 2.04 (br s, 3H), 1.08 (d, J=6.4 Hz, 3H), 1.06 (d, J=6.4 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
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With pyridine; pyridine hydrochloride for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
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With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
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With benzoic acid In toluene for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
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With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
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With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In toluene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1,2-Dihydroxy-3-chlor-propan, i-Propylamin; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: benzoic acid / toluene / 3 h / Heating 2: pyridine / 3 h / 25 °C 3: 1.) NaH / 1.) DMF, 60 deg C, 0.5 h, 2.) DMF, reflux, 16 h 4: 1 N HCl, NaOAc / 5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: benzoic acid / toluene / 3 h / Heating 2: pyridine / 3 h / 25 °C 3: 1.) NaH / 1.) DMF, 60 deg C, 0.5 h, 2.) DMF, reflux, 16 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: benzoic acid / toluene / 3 h / Heating 2: pyridine / 3 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With p-toluenesulfonic acid monohydrate In piperidine; toluene | VII.a (a) (a) 6-(3-Isopropylamino-2-hydroxypropoxy)benzothiazole STR122 A mixture of 6-oxo-5-bromo-4,5,6,7-tetrahydrobenzothiazole (100 parts), 3-isopropylamino-1,2-propanediol (67 parts), p-toluenesulfonic acid monohydrate (99 parts) and toluene (1550 parts) is heated under reflux for 21 hours while drying the refluxing azeotropic mixture according to the method described in Example I. After cooling, the reaction mixture is adjusted to pH 9 by adding aqueous 2.5N-sodium hydroxide and formed organic layer is separated. The organic layer is washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The remaining 4'-isopropylaminomethyl-5-bromo-4,5,6,7-tetrahydrobenzothiazole-6-spiro-2'-[1,3]-dioxolane (156 parts) is dissolved in piperidine (1560 parts), and stirred for 49 hours on an oil bath heated at 95° to 100° C. The reaction mixture is concentrated under reduced pressure to leave residue which is mixed with ethyl acetate and water, shaken and fractionated to separate formed organic layer. The organic layer is washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Residue (172 parts) is recrystallized from ethanol-hydrochloric acid giving 6-(3-isopropylamino-2-hydroxypropoxy)benzothiazole) (65 parts) in 57% yield. mp. 132°-134° C. (hydrochloride trihydrate). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate In methanol Industry scale; | 1.1 A reactor is charged with 392 kg of isopropylaminopropanediol, approximately 240 L of methanol, 6 to 7L of sodium methoxide (30%) and 270 L of dimethylcarbonate. The contents were heated up to allow reaction to occur. Solvent is removed by distillation.200 L water and ca 450 L of methylisobutylketone (MIBK) are then charged to the reactor. The reactor contents are then cooled down to <25°C. Tetrabutylammoniumhydrogensulphate (ca 2.5kg) and 520 kg of benzenesulphonylchloride are then added to the vessel under cooling. 30% sodium hydroxide is added to the reactorThe reactor contents are heated and phase separation performed, removing the aqueous layer. Solvent is distilled and the product oxazolidone sulphonate is isolated from methyl-tert-butylether (MTBE).Fig. 1 illustrates the infra red spectrum of oxazolidinone sulphate.Purity HPLC >98% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With titanium(IV) oxide; oxygen UV-irradiation; |
Yield | Reaction Conditions | Operation in experiment |
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With P25; dihydrogen peroxide; oxygen UV-irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dihydrogen peroxide In aq. phosphate buffer at 20℃; UV-irradiation; Photolysis; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With diamide In dichloromethane at 25℃; Inert atmosphere; | 1-3 Example 2 Under the protection of nitrogen, add 500ml of dichloromethane, 100g of 4-isopropoxyethoxymethylphenol, 190g of 3-isopropylamino-1,2-propanediol and 374.7g of triphenylphosphine resin to a 2000ml four-necked flask. , At room temperature 25, add dropwise N,N,N',N'-tetramethylazodicarbonamide (TMAD) 246g for reaction, after the reaction is complete, filter, add 2000ml of water, extract with 1000g of dichloromethane, concentrate the organic Phase, 142.6 g of bisoprolol free base was obtained, the yield was 92%, and the purity was 99.09%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1at% Cu-doped TiO2 at 25℃; for 0.583333h; UV-irradiation; | 2.4. Photodegradation tests General procedure: The degradation of metoprolol was evaluated by photocatalysis andphoto-Fenton-like processes in a batch reactor with a total volume of 0.1L. The initial metoprolol concentration was 50 mg/L, which correspondsto the actual concentration that may come from some industrial discharges[20]. The catalyst loading was 0.4 g L -1 [21,22] and was keptcompletely dispersed in the photo-reactor by continuous stirring. Thesource of radiation was a UV lamp placed inside the reactor with amonochromatic emission at 254 nm, a power of 8 W and an averageradiation intensity of 166 W m -2. The reactor was a glass cylinder (2.5cm wide) and the lamp was placed at the center. The metoprolol solutionwas maintained at constant temperature (25 °C) by a thermal bath. Theprocedure of a typical experiment was as follows: batch reactor withmetoprolol solution, followed by the addition of photocatalyst andfinally turning on the radiation source (254 nm radiation from a lampplaced at the center of the reactor). For reactions that required hydrogenperoxide, this was incorporated in stoichiometric amount, according tothe reaction of total MET mineralization, just before the lamp wasturned on. All experiments were carried out at natural pH (pH0 ≈ 5.6). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1at% Cu-doped TiO2 at 25℃; for 0.583333h; Photolysis; | 2.4. Photodegradation tests General procedure: The degradation of metoprolol was evaluated by photocatalysis andphoto-Fenton-like processes in a batch reactor with a total volume of 0.1L. The initial metoprolol concentration was 50 mg/L, which correspondsto the actual concentration that may come from some industrial discharges[20]. The catalyst loading was 0.4 g L -1 [21,22] and was keptcompletely dispersed in the photo-reactor by continuous stirring. Thesource of radiation was a UV lamp placed inside the reactor with amonochromatic emission at 254 nm, a power of 8 W and an averageradiation intensity of 166 W m -2. The reactor was a glass cylinder (2.5cm wide) and the lamp was placed at the center. The metoprolol solutionwas maintained at constant temperature (25 °C) by a thermal bath. Theprocedure of a typical experiment was as follows: batch reactor withmetoprolol solution, followed by the addition of photocatalyst andfinally turning on the radiation source (254 nm radiation from a lampplaced at the center of the reactor). For reactions that required hydrogenperoxide, this was incorporated in stoichiometric amount, according tothe reaction of total MET mineralization, just before the lamp wasturned on. All experiments were carried out at natural pH (pH0 ≈ 5.6). |