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CAS No. : | 1370467-88-1 | MDL No. : | MFCD27964212 |
Formula : | C9H5BrN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MESWGGOFRUNGLK-UHFFFAOYSA-N |
M.W : | 237.05 | Pubchem ID : | 118486152 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
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 |
---|---|---|
Multi-step reaction with 4 steps 1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2: ammonia / water; ethanol / 3 h / 90 °C 3: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4: tetrahydrofuran / 3 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2: ammonia / water; ethanol / 3 h / 90 °C 3: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4: tetrahydrofuran / 3 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2.1: ammonia / water; ethanol / 3 h / 90 °C 3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4.1: phosphorus pentachloride / diethyl ether / 0.67 h 4.2: 1 h / 0 - 20 °C 4.3: 4 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2: ammonia / water; ethanol / 3 h / 90 °C 3: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4: tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2.1: ammonia / water; ethanol / 3 h / 90 °C 3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4.1: pyridine / N,N-dimethyl-formamide; tetrahydrofuran / 4 h 4.2: 0.33 h / 150 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With pyridine; sodium dihydrogen phosphate monohydrate; acetic acid In water at 10 - 50℃; for 2h; | 1.1 Synthesis of Compound B [0054] Compound A (40 g, 168 mmol) was dispersed in acetic acid (400 mL), added with water (400 mL) and pyridine(800 mL), and then the temperature of the mixture thus formed was lowered to 10°C. The mixture was added with sodiumphosphate monobasic monohydrate (280 g, 2.01 mol), and then further added with Raney Ni (101 g) in water (70 mL)to form a reaction solution. The reaction solution was heated to 50°C, allowed to react for 2 hours. Upon the completionof the reaction, the solution was cooled and filtered. The solution was washed with ethyl acetate (EA, 2.5 L), and thefiltrate was added with water (800 mL) for extraction. An organic layer thus formed was separated, and concentratedunder reduced pressure. Cooled water (800 mL) was added thereto, and a solid thus obtained was filtered and dried toobtain Compound B (26.7 g, yield: 66%).[0055] 1H-NMR Spectrum(300 MHz, DMSO-d6): 11.10(s, 1H), 9.15 (s, 1H), 7.95(d, J=8.1Hz, 1H), 7.78 (d, J=8.1Hz,1H), 4.41(s, 2H)[0056] LCMS [M+1]: 241.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2: ammonia / water; ethanol / 3 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2: ammonia / water; ethanol / 3 h / 90 °C 3: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2.1: ammonia / water; ethanol / 3 h / 90 °C 3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4.1: pyridine / N,N-dimethyl-formamide; tetrahydrofuran / 4 h 4.2: 3 h / 20 °C 4.3: 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2: ammonia / water; ethanol / 3 h / 90 °C 3: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4: tetrahydrofuran / 4 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2.1: ammonia / water; ethanol / 3 h / 90 °C 3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4.1: phosphorus pentachloride / diethyl ether / 1 h 4.2: 2 h / 0 - 20 °C 4.3: 3 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2: ammonia / water; ethanol / 3 h / 90 °C 3: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4: tetrahydrofuran / 3 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2.1: ammonia / water; ethanol / 3 h / 90 °C 3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4.1: phosphorus pentachloride / diethyl ether / 1 h 4.2: 2 h / 0 - 20 °C 4.3: 4 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2: ammonia / water; ethanol / 3 h / 90 °C 3: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4: tetrahydrofuran / 3 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2.1: ammonia / water; ethanol / 3 h / 90 °C 3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4.1: pyridine / N,N-dimethyl-formamide; tetrahydrofuran / 4 h 4.2: 12 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2.1: ammonia / water; ethanol / 3 h / 90 °C 3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4.1: phosphorus pentachloride / diethyl ether / 0.67 h 4.2: 1 h / 0 - 20 °C 4.3: 3 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2: ammonia / water; ethanol / 3 h / 90 °C 3: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4: sodium hydrogencarbonate / methanol / 4 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2.1: ammonia / water; ethanol / 3 h / 90 °C 3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4.1: triethylamine; diphenyl phosphoryl azide / tetrahydrofuran / 2 h / 20 °C 4.2: 4 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2.1: ammonia / water; ethanol / 3 h / 90 °C 3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4.1: phosphorus pentachloride / diethyl ether / 0.67 h 4.2: 1 h / 0 - 20 °C 4.3: 6 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2.1: ammonia / water; ethanol / 3 h / 90 °C 3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4.1: triethylamine; diphenyl phosphoryl azide / tetrahydrofuran / 1 h / 20 °C 4.2: 4 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2: ammonia / water; ethanol / 3 h / 90 °C 3: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4: 4 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2: ammonia / water; ethanol / 3 h / 90 °C 3: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4: 4 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: acetic acid; sodium dihydrogen phosphate monohydrate; pyridine / water / 2 h / 10 - 50 °C 2: ammonia / water; ethanol / 3 h / 90 °C 3: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene; acetone; acetonitrile / 14 h / 80 - 85 °C 4: 4 h / 90 °C |
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