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Chemical Structure| 17543-94-1 Chemical Structure| 17543-94-1

Structure of 17543-94-1

Chemical Structure| 17543-94-1

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Product Details of [ 17543-94-1 ]

CAS No. :17543-94-1
Formula : C5H5BrN2O
M.W : 189.01
SMILES Code : NC(=O)C1=CC=C(Br)N1
English Name :5-Bromo-1H-pyrrole-2-carboxamide
MDL No. :MFCD09801029

Safety of [ 17543-94-1 ]

Application In Synthesis of [ 17543-94-1 ]

* 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 [ 17543-94-1 ]

[ 17543-94-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 4513-94-4 ]
  • [ 17543-94-1 ]
  • [ 34649-20-2 ]
  • [ 196106-96-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dihydrogen peroxide; potassium carbonate / dimethyl sulfoxide / 1.5 h / 0 - 20 °C 2: Ascophyllum nodosum vanadate(V)-dependent bromoperoxidase I; dihydrogen peroxide; sodium bromide / water; <i>tert</i>-butyl alcohol / 72 h / 23 °C / pH 6.2 / aq. buffer; Enzymatic reaction
  • 2
  • [ 4551-72-8 ]
  • [ 17543-94-1 ]
  • [ 34649-20-2 ]
  • [ 196106-96-4 ]
YieldReaction ConditionsOperation in experiment
9% With 4-morpholineethanesulfonic acid; VBrPO(AnI) bromoperoxidase; dihydrogen peroxide; sodium bromide In water; <i>tert</i>-butyl alcohol at 20℃; Overall yield = 51 %;
With Ascophyllum nodosum vanadate(V)-dependent bromoperoxidase I; dihydrogen peroxide; sodium bromide In water; <i>tert</i>-butyl alcohol at 23℃; for 72h; aq. buffer; Enzymatic reaction; regioselective reaction; 4.2. General method for pyrrole bromination in bromoperoxidase-catalyzed reactions General procedure: A solution of H2O2 (3×2.0 mL, 0.825 M) and NaBr (3×154.4 mg, 1.50 mmol) in MES-buffer (500 mM, pH 6.2) was added every day with a syringe pump (8 h, 0.004 mL/min) to a solution of substrate 1 (1.50 mmol) and VBrPO(AnI) (34.6 UT, 0.032 mmol%) in MES-buffer (500 mM, pH 6.2, 20.0 ml) and tBuOH (6.6 mL) [for: 1f 3× H2O2 (2.0 mL, 0.511 M) and NaBr (95.7 mg, 0.93 mmol) in MES-buffer 500 mM to a solution of 1f (0.93 mmol) and VBrPO(AnI) (21.5 UT, 0.032 mmol%) in MES-buffer (500 mM, pH 6.2, 10.1 ml) and tBuOH (4.1 mL)]. The reaction mixture was stirred at 23 °C for 3 days. The aqueous layer was extracted with Et2O (3×20 mL). Combined organic extracts were dried (MgSO4). The solvent was removed under reduced pressure (14 mbar, 40 °C) to afford a product mixture, which was analyzed by 1H NMR and GC, using pentachlorobenzene (1H NMR) as an internal standard in comparison to spectral data from authentic references. New compounds were purified via column chromatography and fully characterized. pH and bromoperoxidase activity (triiodide assay) were determined from the aqueous layer.
 

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