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CAS No. : | 164464-57-7 | MDL No. : | MFCD14581996 |
Formula : | C6H3ClF3NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CBLBIGVHQINGIW-UHFFFAOYSA-N |
M.W : | 197.54 | Pubchem ID : | 19066116 |
Synonyms : |
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Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 | UN#: | 2811 |
Hazard Statements: | H301-H311-H331 | 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 |
---|---|---|
93.5% | With urea hydrogen peroxide adduct; trifluoroacetic acid In dichloromethane at 0 - 20℃; for 16h; | 1 Step 1. Synthesis of 2-chloro-3-(trifluoromethyl)pyridine 1-oxide The title compound was prepared analogous to the literature procedure (US2008/0275057).To a stirred solution of 2-chloro-3-(trifluoromethyl)pyridine (75.0 g, 413.13 minol) in DCM (750mL) was added UHP (79.7 g, 846.92 minol). The solution was cooled to 0°C with ice-bath and TFAA (114.0 mL, 913.02 minol) was added dropwise. After completion of addition, reaction mixture was stirred at ii for 16 h. Then the reaction mixture was diluted with ice-water and neutralized with Na2CO3, organic portion was separated and the aqueous portion wasextracted with DCM twice. The combined organic portion was washed with brine solution, dried over anhydrous Na2SO4 and concentrated. The crude mass was triturated with 5% DCM in hexane, solid separated was collected by filtration and dried under vacuum to afford the product as a white solid (76.3 g, 93.5%). LC/MS, ESl-MS(): 197.9. 1H NMR (400 MHz, CDCI3) O ppm 8.72 (dd, J= 6.8, 1.2 Hz, 1 H), 7.80 (d, J= 8.4 Hz, 1 H), 7.60 (t, J= 7.2 Hz, 1 H). |
10.12.10 10. 10. 2-Chloro-3-trifluoromethyl pyridine-1-oxide Prepared from 2-chloro-3-trifluoromethyl pyridine (Fluorochem Limited, Wesley St., Old Glossop, Derbyshire SK13 9RY, United Kingdom). mp 97°-98° C. Anal. calcd. for C6 H3 ClF3 NO: C 36.48; H 1.53; N 7.09. Found: C 36.13; H 1.34; N 6.88. m/e calcd. for C6 H3 ClF3 NO: 197.5451. Found: 196.98306. | ||
With urea hydrogen peroxide adduct; trifluoroacetic anhydride In dichloromethane at 0 - 20℃; for 4h; | 9.17 To a solution of starting material (9.26 g, 0.05 mol), UHP (9.9 g, 0.105 mol) was added. With ice-bath, TFAA (21 g, 0.100 mol) was added dropwise. After addition, the reaction was maintained at room temperature. for 4 hrs. Neutralize the reaction with Na2CO3 (aq.) and the mixture was extracted with DCM for 3 times. The organic layer was collected, dried and concentrated and purified by flash chromatography (PE:EA=3:1) to give the pure product 8.1 g. |
8.1 g | With urea hydrogen peroxide adduct; trifluoroacetic acid In dichloromethane at 20℃; for 4h; Cooling with ice; | 7.DDD.EEE EEE. Intermediate 28 To a solution of starting material (9.26 g, 0.05 mol), UHP (9.9 g, 0.105 mol) was added. With ice-bath, TFAA (21 g, 0.100 mol) was added dropwise. After addition, the reaction was maintained at room temperature for 4 hrs. Neutralize the reaction with Na2CC>3 (aq.) and the mixture was extracted with DCM for 3 times. The organic layer was collected, dried and concentrated and purified by flash chromatography (PE:EA=3:1) to give the pure product (intermediate 28) 8.1 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-chloro-3-(trifluoromethyl)pyridine-1-oxide; phenylboronic acid With sodium carbonate In water; toluene at 20℃; Stage #2: In water; toluene for 3h; Heating / reflux; | 9.17 A solution of compound 28 (0.8 g, 4.07 mmol) and in 2 ml Na2CO3 (aq. 2N) and 3 ml toluene was stirred under an atmosphere of N2 and at room temperature. Then Pd(PPh3)4 was added. The mixture was stirred under reflux at an atmosphere of N2 for 3 hrs. Then the solvent was removed under vacuum. The residue was treated with water and extracted with EA, and the organic phase was collected, dried and concentrated to be purified by recrystallization to give. 0.75 g of pale yellow powder. | |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene Inert atmosphere; Reflux; | 7.DDD.FFF FFF. Intermediate 29 A solution of intermediate compound 28 (0.8 g, 4.07 mmol) and in 2 ml Na2CC>3 (aq. 2N) and 3 ml toluene was stirred under an atmosphere of N2 and at room temperature. Then Pd(PPli3)4 was added. The mixture was stirred under reflux at an atmosphere of N2 for 3 hrs. Then the solvent was removed under vacuum. The residue was treated with water and extracted with EA, and the organic phase was collected, dried and concentrated to be purified by recrystallization to give. 0.75 g of pale yellow powder as intermediate 29. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: 2-chloro-3-(trifluoromethyl)pyridine-1-oxide; 2-Methylphenylboronic acid With sodium carbonate In water; toluene for 0.166667h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In water; toluene at 110℃; for 16h; Inert atmosphere; | 2 Step 2. Synthesis of 2-(o-tolyl)-3-(trifluoromethyl)pyridine 1-oxide The title compound was prepared analogous to the literature procedure (US2008/0275057).A solution of 2-chloro-3-(trifluoromethyl)pyridine 1-oxide (30.0 g, 151.87 minol) in toluene (450mL) and water (300 mL) was added o-tolylboronic acid (20.7 g, 151 .87 minol), Na2CO3 (62.8 g,597.61 minol) and stirred under N2 for 10 min Then Pd(PPh3)4 (8.8 g, 7.61 minol) was addedand the reaction mixture was stirred under reflux in a N2 atmosphere for 16 h. Reaction mixture was cooled to rt, diluted with EtOAc-water, organic portion was separated and the aqueous portion was extracted with EtOAc twice. Combined organic portion was washed with brine solution, dried over anhydrous Na2SO4 and concentrated. The crude mass was crystallized from EtOAc-Hexane to afford 27 g (70%) product as an off white solid. LC/MS,ESl-MS(): 254.05.. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium carbonate / toluene; water / 0.17 h / Inert atmosphere 1.2: 16 h / 110 °C / Inert atmosphere 2.1: trichlorophosphate / 16 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium carbonate / toluene; water / 0.17 h / Inert atmosphere 1.2: 16 h / 110 °C / Inert atmosphere 2.1: trichlorophosphate / 16 h 3.1: ammonium acetate / dimethyl sulfoxide / 18 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium carbonate / toluene; water / 0.17 h / Inert atmosphere 1.2: 16 h / 110 °C / Inert atmosphere 2.1: trichlorophosphate / 16 h 3.1: methanesulfonato(2-di-t-butylphosphino-2’,4’,6’-tri-i-propyl-1,1'-biphenyl)(2’-amino-1,1'-biphenyl-2-yl)palladium(II); caesium carbonate / 1,4-dioxane / 80 °C / Inert atmosphere | ||
Multi-step reaction with 4 steps 1.1: sodium carbonate / toluene; water / 0.17 h / Inert atmosphere 1.2: 16 h / 110 °C / Inert atmosphere 2.1: trichlorophosphate / 16 h 3.1: ammonium acetate / dimethyl sulfoxide / 18 h / 130 °C 4.1: pyridine / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; water / 16 h / 110 °C / Inert atmosphere 2: trichlorophosphate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; water / 16 h / 110 °C / Inert atmosphere 2: trichlorophosphate 3: ammonium hydroxide / 1,4-dioxane / 16 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; water / 16 h / 110 °C / Inert atmosphere 2: trichlorophosphate 3: ammonium hydroxide / 1,4-dioxane / 16 h / 100 °C 4: pyridine / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; water / 16 h / 110 °C / Inert atmosphere 2: trichlorophosphate 3: ammonium hydroxide / 1,4-dioxane / 16 h / 100 °C 4: pyridine 5: hydrogenchloride / 1,4-dioxane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium carbonate / toluene; water / 0.17 h / Inert atmosphere 1.2: 16 h / 110 °C / Inert atmosphere 2.1: trichlorophosphate / 16 h 3.1: methanesulfonato(2-di-t-butylphosphino-2’,4’,6’-tri-i-propyl-1,1'-biphenyl)(2’-amino-1,1'-biphenyl-2-yl)palladium(II); caesium carbonate / 1,4-dioxane / 80 °C / Inert atmosphere 4.1: acetonitrile / 16 h / 120 °C / Large scale | ||
Multi-step reaction with 5 steps 1.1: sodium carbonate / toluene; water / 0.17 h / Inert atmosphere 1.2: 16 h / 110 °C / Inert atmosphere 2.1: trichlorophosphate / 16 h 3.1: ammonium acetate / dimethyl sulfoxide / 18 h / 130 °C 4.1: pyridine / 2 h / 0 - 20 °C 5.1: acetonitrile / 16 h / 120 °C / Large scale |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium carbonate / toluene; water / 0.17 h / Inert atmosphere 1.2: 16 h / 110 °C / Inert atmosphere 2.1: trichlorophosphate / 16 h 3.1: methanesulfonato(2-di-t-butylphosphino-2’,4’,6’-tri-i-propyl-1,1'-biphenyl)(2’-amino-1,1'-biphenyl-2-yl)palladium(II); caesium carbonate / 1,4-dioxane / 80 °C / Inert atmosphere 4.1: acetonitrile / 16 h / 120 °C / Large scale 5.1: hydrogenchloride / dichloromethane; isopropyl alcohol / 4.5 h / 20 °C | ||
Multi-step reaction with 6 steps 1.1: sodium carbonate / toluene; water / 0.17 h / Inert atmosphere 1.2: 16 h / 110 °C / Inert atmosphere 2.1: trichlorophosphate / 16 h 3.1: ammonium acetate / dimethyl sulfoxide / 18 h / 130 °C 4.1: pyridine / 2 h / 0 - 20 °C 5.1: acetonitrile / 16 h / 120 °C / Large scale 6.1: hydrogenchloride / dichloromethane; isopropyl alcohol / 4.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium carbonate / toluene; water / 0.17 h / Inert atmosphere 1.2: 16 h / 110 °C / Inert atmosphere 2.1: trichlorophosphate / 16 h 3.1: methanesulfonato(2-di-t-butylphosphino-2’,4’,6’-tri-i-propyl-1,1'-biphenyl)(2’-amino-1,1'-biphenyl-2-yl)palladium(II); caesium carbonate / 1,4-dioxane / 80 °C / Inert atmosphere 4.1: acetonitrile / 16 h / 120 °C / Large scale 5.1: hydrogenchloride / 20 °C | ||
Multi-step reaction with 6 steps 1.1: sodium carbonate / toluene; water / 0.17 h / Inert atmosphere 1.2: 16 h / 110 °C / Inert atmosphere 2.1: trichlorophosphate / 16 h 3.1: ammonium acetate / dimethyl sulfoxide / 18 h / 130 °C 4.1: pyridine / 2 h / 0 - 20 °C 5.1: acetonitrile / 16 h / 120 °C / Large scale 6.1: hydrogenchloride / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium carbonate / toluene; water / 0.17 h / Inert atmosphere 1.2: 16 h / 110 °C / Inert atmosphere 2.1: trichlorophosphate / 16 h 3.1: methanesulfonato(2-di-t-butylphosphino-2’,4’,6’-tri-i-propyl-1,1'-biphenyl)(2’-amino-1,1'-biphenyl-2-yl)palladium(II); caesium carbonate / 1,4-dioxane / 80 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere | ||
Multi-step reaction with 5 steps 1.1: sodium carbonate / toluene; water / 0.17 h / Inert atmosphere 1.2: 16 h / 110 °C / Inert atmosphere 2.1: trichlorophosphate / 16 h 3.1: ammonium acetate / dimethyl sulfoxide / 18 h / 130 °C 4.1: pyridine / 2 h / 0 - 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; water / 16 h / 110 °C / Inert atmosphere 2: trichlorophosphate 3: ammonium hydroxide / 1,4-dioxane / 16 h / 100 °C 4: pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 110℃; for 16h; Inert atmosphere; | 1 Step 2. Synthesis of rac-tert-butyl (1 SR,6R5,75R)-2-azabicyclo[4.2.O]octane-7- carboxylate In a vial, crude rac-tert-butyl (1 SR,6RS,7SR)-3-oxo-2-azabicyclo[4.2.0]octane-7-carboxylate(476.2 mg, 2.114 minol) was taken up in THF (Volume: 10 mL), the solution was cooled toO°C, then BH3-THF (2.54 mL, 2.54 minol) was added and the reaction was allowed to warm toRT for 16 h. No anticipated product was observed by LMCS, likely due to poor quality BH3-THF. The reaction was cooled to 0 °C, and additional BH3-THF (2.54 mL, 2.54 minol) wasadded from a new bottle, and the reaction was allowed to warm to RT. After stirring for 3 d, reaction was again cooled to 0 °C and a third portion of BH3-THF (2.54 mL, 2.54 minol) was added. After stirring for 16 h, the reaction was cooled to 0 °C, quenched with AcOH, andconcentrated. The resulting residue was dissolved in EtOAc and the organics were washedwith sat. aq. NaHCO3 and brine, dried over MgSO4, and concentrated in vacuo to give the crude title product Intermediate (16): rac-tert-butyl (1 SR,6RS,7SR)-2-azabicyclo[4 .2 .0]octane-7-carboxylate that was used directly without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium carbonate / water; toluene / 20 °C 1.2: 3 h / Heating / reflux 2.1: trichlorophosphate / 5 h / Heating / reflux | ||
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; toluene / Inert atmosphere; Reflux 2: trichlorophosphate / 5 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium carbonate / water; toluene / 20 °C 1.2: 3 h / Heating / reflux 2.1: trichlorophosphate / 5 h / Heating / reflux 3.1: urea hydrogen peroxide adduct; trifluoroacetic anhydride / dichloromethane / 0 - 20 °C | ||
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; toluene / Inert atmosphere; Reflux 2: trichlorophosphate / 5 h / Reflux 3: urea hydrogen peroxide adduct; trifluoroacetic acid / dichloromethane / 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium carbonate / water; toluene / 20 °C 1.2: 3 h / Heating / reflux 2.1: trichlorophosphate / 5 h / Heating / reflux 3.1: urea hydrogen peroxide adduct; trifluoroacetic anhydride / dichloromethane / 0 - 20 °C 4.1: trichlorophosphate / 4 h / Heating / reflux | ||
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; toluene / Inert atmosphere; Reflux 2: trichlorophosphate / 5 h / Reflux 3: urea hydrogen peroxide adduct; trifluoroacetic acid / dichloromethane / 20 °C / Cooling with ice 4: trichlorophosphate / 4 h / Reflux |