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[ CAS No. 823803-51-6 ] {[proInfo.proName]}

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Chemical Structure| 823803-51-6
Chemical Structure| 823803-51-6
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Product Details of [ 823803-51-6 ]

CAS No. :823803-51-6 MDL No. :MFCD09907847
Formula : C10H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :222.08 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 823803-51-6 ]

* 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.

  • Downstream synthetic route of [ 823803-51-6 ]

[ 823803-51-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 53078-85-6 ]
  • [ 56-81-5 ]
  • [ 823803-51-6 ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 2-bromo-5-methylaniline; glycerol With sulfuric acid; nitrobenzene In water at 150℃; for 3h; Stage #2: With sodium hydroxide In water 36.2 Step 2:A mixture of compound 36b (3.3 g, 17.7 mmol), glycerin (3.3 g, 35.5 mmol), nitrobenzene (2.2 g, 17.7 mmol) and 75% aqueous sulfuric acid (10 mL, 138 mmol) is stirred at 1500C for 3 h (mixture turns black and viscous). The reaction mixture is cooled down, poured into ice-water (200 mL) and 10 N aqueous NaOH is added (30 mL, 300 mmol). The black mixture is then shaken with EtOAc (100 mL) and is centrifuged in 50 mL portions. The upper EtOAc layers are combined and the bottom aqueous layers containing the black tar are shaken with EtOAc and re-centrifuged. All EtOAc extracts are combined, washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to give 4.8 g of a brown-red oil. This material is chromatographed on 80 g silica gel column (CombiFlash Companion apparatus, hexanes-EtOAc gradient). The fractions containing the compound are concentrated under vacuum to afford compound 36c as a white solid (3.26 g, 83% yield).
83% Stage #1: 2-bromo-5-methylaniline; glycerol With sulfuric acid; nitrobenzene In water at 150℃; for 3h; Stage #2: With sodium hydroxide In water at 0℃; 36.2 A mixture of compound 36b (3.3 g, 17.7 mmol), glycerin (3.3 g, 35.5 mmol), nitrobenzene (2.2 g, 17.7 mmol) and 75% aqueous sulfuric acid (10 ml_, 138 mmol) is stirred at 1500C for 3 h (mixture turns black and viscous). The reaction mixture is cooled down, poured into 200 ml. ice-water and 10 N aqueous NaOH is added (30 ml_, 300 mmol). The black mixture is then shaken with 100 ml. EtOAc and is centrifuged in 50 ml_ portions. The upper EtOAc layers are combined and the bottom aqueous layers containing the black tar are shaken with EtOAc and re-centrifuged. All EtOAc extracts are combined, washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to give 4.8 g of a brown-red oil. This material is chromatographed on 80 g silica gel column (CombiFlash Companion apparatus, hexanes-EtOAc gradient). The fractions containing the compound are concentrated under vacuum to afford compound 36c as a white solid (3.26 g, 83% yield).
83% Stage #1: 2-bromo-5-methylaniline; glycerol With sulfuric acid; nitrobenzene In water at 150℃; for 3h; Stage #2: With sodium hydroxide In water at 0℃; 36.2 A mixture of compound 36b (3 3 g, 17 7 mmol), glycerin (3 3 g, 35 5 mmol), nitrobenzene (2 2 g, 17 7 mmol) and 75% aqueous sulfuric acid (10 mL, 138 mmol) is stirred at 15O0C for 3 h (mixture turns black and viscous) The reaction mixture is cooled down, poured into ice-water (200 mL) and 10 N aqueous NaOH is added (30 mL, 300 mmol) The black mixture is then shaken with EtOAc (100 mL) and is centrifuged in 50 mL portions The upper EtOAc layers are combined and the bottom aqueous layers containing the black tar are shaken with EtOAc and re-centϖfuged All EtOAc extracts are combined, washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to give 4.8 g of a brown-red oil. This material is chromatographed on 80 g silica gel column (CombiFlash Companion apparatus, hexanes/EtOAc gradient). The fractions containing the compound are concentrated under vacuum to afford compound 36c as a white solid (3.26 g, 83% yield).
83% Stage #1: 2-bromo-5-methylaniline; glycerol With sulfuric acid; nitrobenzene In water at 150℃; for 3h; Stage #2: With sodium hydroxide In water 36.2 A mixture of compound 36b (3.3 g, 17.7 mmol), glycerin (3.3 g, 35.5 mmol), nitrobenzene (2.2 g, 17.7 mmol) and 75% aqueous sulfuric acid (10 ml_, 138 mmol) is stirred at 1500C for 3 h (mixture turns black and viscous). The reaction mixture is cooled down, poured into ice-water (200 ml.) and 10 N aqueous NaOH is added (30 ml_, 300 mmol). The black mixture is then shaken with EtOAc (100 ml.) and is centrifuged in 50 mL portions. The upper EtOAc layers are combined and the bottom aqueous layers containing the black tar are shaken with EtOAc and re-centrifuged. All EtOAc extracts are combined, washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to give a brown-red oil. This material is chromatographed on 80 g silica gel column (CombiFlash Companion apparatus, hexane-EtOAc gradient). The fractions containing the compound are concentrated under vacuum to afford compound 36c as a white solid (3.26 g, 83% yield).
67% With sulfuric acid; nitrobenzene at 150℃; for 3h;
52% With nitrobenzene In sulfuric acid at 140℃; for 3h; 2.1 Step 1. 8-Bromo-5-methylquinoline Step 1. 8-Bromo-5-methylquinoline: A suspension of 2-bromo-5-methylaniline (500 g, 2.69 mol), glycerin (519 g, 5.64mo1), and nitrobenzene (350. g, 2.85 mol) in sulfuric acid (1230 mL, 75%), split into two batches, was stirred at 140 °C for 3 h. After cooling to rt, the two batches were combined and poured into a solution of NaOH (7.5 L,10 M) in ice-water; the mixture was allowed to stand at rt overnight. The undissolved solids were then collected by filtration and dissolved in EtOAc (10 L). The resulting solution was washed with water (10 L) and brine (10 L), dried over Na2SO4, and evaporated. The obtained crude product was purified by column chromatography (EtOAc gradient in PE from 0% to 50%) to afford 8-bromo-5-methylquinoline as a whitesolid (640 g, 52%).
With sulfuric acid In water; nitrobenzene at 150℃; for 3h; 101 Synthesis of 8-bromo-5-methylquinoline (101 A) : To a stirred solution of 2-bromo-5- methyl aniline (1200 g, 6.45 mol) in nitrobenzene (660 ml_) and 75% H2SO4 (3.6 L) was added glycerol (1180 g, 6.45 mol) at RT and then slowly heated to 150 °C for 3 h. Caution: highly exothermic reaction. The mixture was cooled to RT and poured into ice- water while maintaining the temperature below 10 °C. The pH was adjusted ~10 with aq. 10N NaOH and the product was extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated under vacuum to afford crude material. This material was dissolved in DCM/hexanes (5:1) and stirred for 30 minutes. The solid was filtered off and the filtrate was evaporated under reduced pressure to afford 101 A.
With sulfuric acid In nitrobenzene at 20 - 150℃; for 3h; 1 Example 1 Synthesis of 8-bromo-5-methylquinoline (1A): To a stirred solution of 2-bromo-5- methyl aniline (1200 g, 6.45 mol) in nitrobenzene (660 ml_) and 75% H2SO4 (3.6 L) was added glycerol (1180 g, 6.45 mol) at RT and then slowly heated to 150 °C for 3 h. The mixture was cooled to RT and poured into ice-water while maintaining the temperature below 10 °C. The pH was adjusted ~10 with aqueous 10N NaOH and the product was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated under vacuum to afford material that was dissolved in DCM/hexanes (5:1) and stirred for 30 minutes. The solid was filtered off and the filtrate was evaporated under reduced pressure to afford 1A. NBS, Benzene

  • 2
  • [ 823803-51-6 ]
  • [ 943847-26-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane 2: N,N-dimethyl-formamide 3: potassium carbonate / methanol 4: Dess-Martin periodane / dichloromethane
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