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[ CAS No. 913836-27-8 ]

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Chemical Structure| 913836-27-8
Chemical Structure| 913836-27-8
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Product Details of [ 913836-27-8 ]

CAS No. :913836-27-8 MDL No. :MFCD09027285
Formula : C14H20BBrO3 Boiling Point : 391.9°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :327.02 g/mol Pubchem ID :-
Synonyms :

Safety of [ 913836-27-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 913836-27-8 ]

  • Downstream synthetic route of [ 913836-27-8 ]

[ 913836-27-8 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 1025506-08-4 ]
  • [ 913836-27-8 ]
  • [ 1613415-61-4 ]
YieldReaction ConditionsOperation in experiment
99% With methanol; Rh(1+)*HO(1-)*C20H18 In 1,4-dioxane at 80℃; for 48h; Schlenk technique; Inert atmosphere; enantioselective reaction;
  • 2
  • [ 913836-27-8 ]
  • [ 288-36-8 ]
  • 2-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)-2H-1,2,3-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With potassium carbonate; potassium iodide; In dimethyl sulfoxide; at 80℃; for 1h; To a flask was added 2-(4-(2-bromoethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.750 g, 2.293 mmol, Combi Blocks), KI (0.057 g, 0.344 mmol) and K2CO3 (1.27 g, 9.17 mmol) in DMSO (10 mL) followed by 2H-1,2,3-triazole (0.317 g, 4.59 mmol, TCI). The mixture was heated to about 80 C. for about 1 h then cooled to rt. The mixture was filtered and the filtrate was concentrated in vacuo. The crude material was purified by silica gel flash chromatography eluting with 0 to 50% EtOAc/DCM to provide 2-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)-2H-1,2,3-triazole (0.313 g, 43%): LC/MS (Table 3, Method e) Rt=0.74 min; MS m/z: 316 (M+H)+.
43% With potassium carbonate; potassium iodide; In dimethyl sulfoxide; at 80℃; for 1h; To a flask was added 2-(4-(2-bromoethoxy)phenyl)-4,4,5,5-tetramethyl-l,3,2- dioxaborolane (0.750 g, 2.293 mmol, Combi Blocks), KI (0.057 g, 0.344 mmol) and K2C03 (1.27 g, 9.17 mmol) in DMSO (10 mL) followed by 2H-l,2,3-triazole (0.317 g, 4.59 mmol, TCI). The mixture was heated to about 80 C for about 1 h then cooled to rt. The mixture was filtered and the filtrate was concentrated in vacuo. The crude material was purified by silica gel flash chromatography eluting with 0 to 50% EtOAc/DCM to provide 2-(2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)ethyl)-2H-l,2,3- triazole (0.313 g, 43%): LC/MS (Table 3, Method e) Rt = 0.74 min; MS m z: 316 (M+H)+.
  • 3
  • [ 106-93-4 ]
  • [ 269409-70-3 ]
  • [ 913836-27-8 ]
YieldReaction ConditionsOperation in experiment
24% With potassium carbonate; potassium iodide In acetone at 70℃; for 16h; Inert atmosphere; 6.6-1 Synthesis Example 6-1 Under a nitrogen atmosphere, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1.0 g, 4.5 mmol, 1 eq.) and potassium carbonate (0.82 g, 5.9 mmol, 1.3 eq.) were dissolved in acetone (20 ml) and the solution was stirred at room temperature. To the stirred solution were added 1,2-dibromoethane (4.1 g, 22.7 mmol, 22.7 eq.) and potassium iodide (0.02 g, 0.1 mmol, 0.02 eq.) dissolved in acetone (20 ml), and the mixture was stirred at 70° C. overnight (16 hours). After allowing the mixture to cool to room temperature, the mixture was concentrated under reduced pressure. The resulting residue was extracted with methylene chloride, washed with distilled water and saturated brine, dried over sodium sulfate, and then concentrated again under reduced pressure. The resulting residue was purified by flash column chromatography (eluent: chloroform→chloroform/methanol=49/1), to obtain 2-(4-(2-bromoethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as a white solid (359.0 mg, 24%).
20% With potassium carbonate; potassium iodide In acetone at 70℃; for 16h; Inert atmosphere; compound (4), (1.0 g, 4.5 mmol and 1.0 eq.), K2CO3(0.82 g, 5.9 mmol, 1.3 eq.), and acetone (20 ml) were put in and agitated in the 200 ml flask of two lots under a nitrogen atmosphere. Next, what dissolved 1,2-dibromoethane (4.1 g, 22.7 mmol, 22.7 eq.) and KI (0.02 g, 0.1 mmol, 0.02 eq.) in acetone (20 ml) was put into the system of reaction, and it agitated by 70 ** for 16 hours. Extraction, H2O, and sat.NaCl aq. washed by CH2Cl2after ending reaction, and it was made to dry by Na2SO4, and condensed. Separation refinement of the obtained residue is carried out with silica gel flash column chromatography (eluate: chloroform), and it is an object compound (3) (0.446 g, 20% of yield). It obtained as a white individual.
  • 4
  • [ 913836-27-8 ]
  • C28H24N6O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere 2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethanol; toluene; water / 20 h / 100 °C / Inert atmosphere 3: hydrogenchloride / ethanol; water / 0 - 80 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene; water / 17 h / 100 °C / Inert atmosphere 3: hydrogenchloride / ethanol; water / 15 h / 0 - 80 °C / Inert atmosphere
  • 5
  • [ 913836-27-8 ]
  • C28H26N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium azide / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere 2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethanol; toluene; water / 20 h / 100 °C / Inert atmosphere 3: hydrogenchloride / ethanol; water / 0 - 80 °C / Inert atmosphere 4: palladium on activated charcoal; hydrogen / dichloromethane; methanol / 3 h / 40 °C / Inert atmosphere
  • 6
  • [ 913836-27-8 ]
  • C49H37N5O8S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium azide / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere 2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethanol; toluene; water / 20 h / 100 °C / Inert atmosphere 3: hydrogenchloride / ethanol; water / 0 - 80 °C / Inert atmosphere 4: palladium on activated charcoal; hydrogen / dichloromethane; methanol / 3 h / 40 °C / Inert atmosphere 5: tetrahydrofuran; methanol / 3 h / 40 °C / Inert atmosphere
  • 7
  • [ 913836-27-8 ]
  • 2-(4-(2-azidoethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With sodium azide In N,N-dimethyl-formamide at 100℃; for 1h; Inert atmosphere; A compound (5), (350 mg, 1.07 mmol and 1.0 eq.), DMF (10 ml), and NaN3(83 mg, 1.28 mmol, 1.2 eq.) were put into a 50-ml two-lot flask under a nitrogen atmosphere, and stirring was performed in 100 degree C for 1 hour. Extraction, H2O, and sat.NaClaq. washed with toluene after ending reaction, and it was made to dry by Na2SO4, and condensed. And an object compound (6), and (299 mg and 97% of yield) were obtained as a white individual.
97% With sodium azide In N,N-dimethyl-formamide at 100℃; for 1h; Inert atmosphere; 6.6-2 Synthesis Example 6-2 Under a nitrogen atmosphere, 2-(4-(2-bromoethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (350 mg, 1.0 mmol, 1.0 eq.) was dissolved in N,N-dimethyl formamide (10 ml). To the solution was added sodium azide (83 mg, 1.2 mmol, 1.2 eq.), and the mixture was stirred at 100° C. for 1 hour. After completion of the reaction, the resultant was extracted with toluene, washed with distilled water and saturated brine, dried over sodium sulfate, and then concentrated under reduced pressure. This gave 2-(4-(2-azidoethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as a white solid (299.0 mg, 97%).
  • 8
  • [ 913836-27-8 ]
  • 5-(4-(2-azidoethoxy)phenyl)-3-benzylpyrazine-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere 2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethanol; toluene; water / 20 h / 100 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene; water / 17 h / 100 °C / Inert atmosphere
  • 9
  • [ 104-53-0 ]
  • [ 994-30-9 ]
  • [ 913836-27-8 ]
  • C29H45BO4Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With nickel(II) bromide dimethoxyethane; manganese; 1,5-Hexadien; 4,4′,5,5′-Tetrahydro-2,2′-bioxazole In N,N-dimethyl-formamide at 20℃;
  • 10
  • [ 913836-27-8 ]
  • 3-bromo-6-(tetrahydro-2H-pyran-2-yl)-6H-thieno[2,3-e]indazole [ No CAS ]
  • 3-(4-(2-bromoethoxy)phenyl)-6-(tetrahydro-2H-pyran-2-yl)-6H-thieno[2,3-e]indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In water monomer; toluene at 90℃; for 18h; Inert atmosphere;
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