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CAS No. : | 1187933-36-3 | MDL No. : | MFCD12913831 |
Formula : | C11H12BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HXBUGZUYESCKQM-UHFFFAOYSA-N |
M.W : | 254.12 | Pubchem ID : | 53408510 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
8.96 g | With borane-THF In toluene at 0℃; for 4h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: borane-THF / toluene / 4 h / 0 °C / Inert atmosphere; Reflux 2: potassium carbonate; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; water / 5 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: borane-THF / toluene / 4 h / 0 °C / Inert atmosphere; Reflux 2: potassium carbonate; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; water / 5 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: borane-THF / toluene / 4 h / 0 °C / Inert atmosphere; Reflux 2.1: potassium carbonate; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; water / 5 h / 90 °C / Inert atmosphere 3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / 1,2-dichloro-ethane / 2 h / 80 °C / Inert atmosphere 3.2: 0.25 h / Inert atmosphere 3.3: 2 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: borane-THF / toluene / 4 h / 0 °C / Inert atmosphere; Reflux 2.1: potassium carbonate; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; water / 5 h / 90 °C / Inert atmosphere 3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / 1,2-dichloro-ethane / 2 h / 80 °C / Inert atmosphere 3.2: 0.25 h / Inert atmosphere 3.3: 2 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: borane-THF / toluene / 4 h / 0 °C / Inert atmosphere; Reflux 2.1: potassium carbonate; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; water / 5 h / 90 °C / Inert atmosphere 3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / 1,2-dichloro-ethane / 2 h / 80 °C / Inert atmosphere 3.2: 0.25 h / Inert atmosphere 3.3: 2 h / 20 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 20 °C | ||
Multi-step reaction with 4 steps 1.1: borane-THF / toluene / 4 h / 0 °C / Inert atmosphere; Reflux 2.1: potassium carbonate; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; water / 5 h / 90 °C / Inert atmosphere 3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / 1,2-dichloro-ethane / 2 h / 80 °C / Inert atmosphere 3.2: 0.25 h / Inert atmosphere 3.3: 2 h / 20 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine / 5 h / 0 - 20 °C / Inert atmosphere 2: aluminum (III) chloride / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine / 5 h / 0 - 20 °C / Inert atmosphere 2: aluminum (III) chloride / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18.85 g | With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.4% | With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 8h; Inert atmosphere; | 5 Synthesis of intermediate 3: General procedure: At nitrogen protection atmosphere, in a dry three-mouth flask, respectively, add 1.1mmol intermediate 1 and 1mmol intermediate 2, pour 100ml dmf as a solvent, add dry K2CO3 as a base, react at 120 °C for 8 hours, TLC monitor the reaction, after the reaction is complete, the reaction liquid is cooled to room temperature, add water and dichloromethane in turn, wash the reaction liquid with water multiple times, At the same time, the aqueous phase was extracted with dichloromethane and ethyl acetatefor many times, the organic phase was combined, dried with anhydrous Na2 CO3, filtered, and the reaction liquid was dried to obtain a crude product, and the molar amount of intermediate 3 was obtained by recrystallization of ethyl acetate and petroleum ether was 0.76mmol, the reaction yield was: 76%, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 120 °C / Inert atmosphere 2: potassium carbonate; palladium diacetate; tri-tert-butyl phosphine / 12 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 120 °C / Inert atmosphere 2: o-dimethylbenzene / 4 h / 120 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 120 °C / Inert atmosphere 2: o-dimethylbenzene / 4 h / 120 °C / Inert atmosphere 3: iron(0); ammonia hydrochloride; hydrogenchloride; lithium hydroxide monohydrate; methanol / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 120 °C / Inert atmosphere 2: o-dimethylbenzene / 4 h / 120 °C / Inert atmosphere 3: iron(0); ammonia hydrochloride; hydrogenchloride; lithium hydroxide monohydrate; methanol / tetrahydrofuran 4: palladium diacetate; tri-tert-butyl phosphine / toluene / 105 °C / Inert atmosphere; Alkaline conditions |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 120 °C / Inert atmosphere 2: o-dimethylbenzene / 4 h / 120 °C / Inert atmosphere 3: iron(0); ammonia hydrochloride; hydrogenchloride; lithium hydroxide monohydrate; methanol / tetrahydrofuran 4: palladium diacetate; tri-tert-butyl phosphine / toluene / 105 °C / Inert atmosphere; Alkaline conditions 5: potassium carbonate; palladium diacetate; tri-tert-butyl phosphine / 12 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.4% | With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 8h; Inert atmosphere; | 7 Synthesis of intermediate 3: General procedure: At nitrogen protection atmosphere, in a dry three-mouth flask, respectively, add 1.1mmol intermediate 1 and 1mmol intermediate 2, pour 100ml dmf as a solvent, add dry K2CO3 as a base, react at 120 °C for 8 hours, TLC monitor the reaction, after the reaction is complete, the reaction liquid is cooled to room temperature, add water and dichloromethane in turn, wash the reaction liquid with water multiple times, At the same time, the aqueous phase was extracted with dichloromethane and ethyl acetatefor many times, the organic phase was combined, dried with anhydrous Na2 CO3, filtered, and the reaction liquid was dried to obtain a crude product, and the molar amount of intermediate 3 was obtained by recrystallization of ethyl acetate and petroleum ether was 0.76mmol, the reaction yield was: 76%, |
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