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Chemical Structure| 188947-79-7 Chemical Structure| 188947-79-7

Structure of 188947-79-7

Chemical Structure| 188947-79-7

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Product Details of [ 188947-79-7 ]

CAS No. :188947-79-7
Formula : C9H10BrNO
M.W : 228.09
SMILES Code : CN1C2=CC(Br)=CC=C2OCC1
MDL No. :MFCD06658984

Safety of [ 188947-79-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of [ 188947-79-7 ]

* 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 [ 188947-79-7 ]

[ 188947-79-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 50-00-0 ]
  • [ 105655-01-4 ]
  • [ 188947-79-7 ]
YieldReaction ConditionsOperation in experiment
With sodium cyanoborohydride; acetic acid; In tetrahydrofuran; at 70℃; Into a 20-mL microwave tube, were placed a solution of <strong>[105655-01-4]6-bromo-3,4-dihydro-2H-benzo[b][1,4]oxazine</strong> (400 mg, 1.869 mmol, 1.0 equiv.) in THF (5 mL). Then, CH2O (5 mL), CH3COOH (1 mL), NaBH3CN (450 mg, 7.258 mmol, 4.0 equiv.) was added. The resulting solution was stirred overnight at 70 C. in an oil bath. The reaction was monitored by TLC (PE/EA=4/1). Water (5 ml) was added to the mixture and the mixture was stirred for 10 minutes at room temperature. The resulting mixture was evaporated under reduced pressure. The residue was applied onto a silica gel column with PE/EA (95/5) to 6-bromo-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine obtained as a yellow oil. Mass spectrum (EI, m/z): Calcd for C9H10BrNO, 228.0 (M+H), found, 229.7.
With sodium cyanoborohydride; acetic acid; In tetrahydrofuran; at 70℃; Into a 20-mL microwave tube, were placed a solution of <strong>[105655-01-4]6-bromo-3,4-dihydro-2H-benzo[b][1,4]oxazine</strong> (400 mg, 1.869 mmol, 1.0 equiv.) in THF (5 mL). Then, CH2O (5 mL), CH3COOH (1 mL), NaBH3CN (450 mg, 7.258 mmol, 4.0 equiv.) was added. The resulting solution was stirred overnight at 70 C. in an oil bath. The reaction was monitored by TLC (PE/EA=4/1). Water (5 ml) was added to the mixture and the mixture was stirred for 10 minutes at room temperature. The resulting mixture was evaporated under reduced pressure. The residue was applied onto a silica gel column with PE/EA (95/5) to 6-bromo-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine obtained as a yellow oil. Mass spectrum (EI, m/z): Calcd for C9H10BrNO, 228.0 (M+H), found, 229.7.
  • 2
  • [ 105655-01-4 ]
  • [ 74-88-4 ]
  • [ 188947-79-7 ]
YieldReaction ConditionsOperation in experiment
87% With potassium carbonate; In acetonitrile; at 50℃;Inert atmosphere; [Synthesis of Compound E5] (0136) Compound E4 (1.90 g, 8.88 mmol, 1 Eq) was dissolved in acetonitrile (20 mL) in an argon atmosphere, and potassium carbonate (1.98 g, 14.3 mmol, 1.6 Eq) and methyl iodide (3.0 mL, 47.5 mmol, 5 Eq) were added and the combination was stirred overnight at 50 C. After returning the reaction system to room temperature and distilling off the solvent under reduced pressure, the reaction system was diluted by ethyl acetate, the insoluble matter was distilled off by filtration under reduced pressure, and the filtrate was removed under reduced pressure. The residue obtained was purified by medium-pressure silica gel chromatography (eluent: n-hexane/ethyl acetate=98/2 to 90/10), and the target compound E5 (1.77 g, 87%) was obtained as a pale yellow solid. (0137) 1H NMR (CDCl3): delta 6.73-6.70 (m, 2H), 6.61 (d, J=8.0 Hz, 1H), 4.25 (t, J=4.4 Hz, 2H), 3.26 (t, J=4.4 Hz, 2H), 2.86 (s, 3H).; 13C NMR (CDCl3): delta 143.3 (C), 137.9 (C), 120.5 (CH), 117.2 (CH), 114.9 (CH), 113.8 (C), 64.8 (CH2), 48.8 (CH2), 38.7 (CH3).; HRMS-ESI (m/z): [M+H]+ calcd for C9H11BrNO: 228.00185. found: 228.00185. found: 228.00168 (0.2 mDa, 0.8 ppm).
 

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