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Chemical Structure| 915156-09-1 Chemical Structure| 915156-09-1

Structure of 915156-09-1

Chemical Structure| 915156-09-1

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Product Details of [ 915156-09-1 ]

CAS No. :915156-09-1
Formula : C6H5BrN2O3
M.W : 233.02
SMILES Code : OC1=CC([N+]([O-])=O)=CC(Br)=C1N
MDL No. :MFCD18070937

Safety of [ 915156-09-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H315-H317-H318-H410
Precautionary Statements:P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501
Class:9
UN#:3077
Packing Group:

Application In Synthesis of [ 915156-09-1 ]

* 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 [ 915156-09-1 ]

[ 915156-09-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 915156-09-1 ]
  • [ 116632-23-6 ]
YieldReaction ConditionsOperation in experiment
85% Compound 98 (33.0 g, 0.14 mol) was treated with sulfuric acid (13.7 mL) and was refluxed in EtOH (550 mL) for 0.5 hours, followed by addition OfNaNO2 (23.8 g, 0.35 mol). The resulting mixture was refluxed for additional 1 hour and the volatile was evaporated. The residue was taken up with ethyl acetate and water. The layers were separated and the organic layer was washed with water, saturated sodium bicarbonate, and brine. After removal of solvent, the residue was purified by column chromatography on silica gel to afford the title compound (26 g, 85percent); 1H NMR (500 MHz, CD3OD): delta 5.00 (brs, IH), 7.58 (dd, IH, J= 1.7, 2.3 Hz), 7.47 (t, IH, J= 2.1 Hz), 7.69 (t, IH5 J= 1.9 Hz); 13C NMR (125 MHz, CD3OD): delta 110.5, 118.1, 123.7, 125.6, 151.0, 160.5; HRMS (FAB) calcd for C6H4BrNO3 (M+) 216.9375, found 216.9374.
85% 75.6 g (0.32 mmol) of 2-amino-3-bromo-5-nitrophenol prepared in Step 208 1) was dissolved in 1.5 L of 20 ethanol. The mixture was cooled to a temperature of ?10° C. 62.3 mL (1.17 mmol) of 21 sulfuric acid was added thereto at a temperature in a range of ?10° C. to ?2° C. for 30 minutes. The temperature of the reaction mixture was raised to 50° C., and 22 sodium nitrite was slowly added thereto for 30 minutes. The temperature of the reaction mixture was raised to 80° C., and the mixture was stirred under reflux for 3 hours. Once the reaction was complete, a solvent was removed therefrom under reduced pressure, and 11 water and 23 ethyl acetate were added dropwise thereto. An organic layer was extracted therefrom three times, and then washed with saline water. The organic layer was dried using anhydrous sodium sulfate, and then concentrated under reduced pressure. The obtained residue was purified using column chromatography (ethyl acetate:hexane=0.5:10 (v/v)), and the resulting solution was concentrated under reduced pressure to thereby obtain 60 g of a desired compound at a yield of 85percent. (0388) 1H-NMR (300 MHz, DMSO-d6): delta 10.90 (s, 1H), 7.75 (s, 1H), 7.51 (s, 1H), 7.36 (s, 1H).
84% With sulfuric acid; sodium nitrite; In ethanol; at -10 - 55℃; for 3h;Reflux; To a cooled solution (-10° C.) of i (643 g, 2.76 mol) in EtOH (13 L) was added conc. H2SO4 (515 mL, 9.97 mol) over a period of 35 min at -10 to -2° C. The mixture was allowed to warm to RT and then heated to 50-55° C. followed by the portion-wise addition of NaNO2 (671 g, 9.72 mol) over 30 min and the mixture heated at reflux for 3 h. The mixture was concentrated to 3 L and cooled to 0° C. followed by the addition of H2O (5 L) and extraction with EtOAc (3*6 L). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was treated with 25percent ether-hexane mixture (6 L) and stirred for 1 h, filtered and the solid and washed with hexane (3 L) to obtain ii (505 g, 84percent).
82% 3-Bromo-5-nitro-phenolTo an ice-cold solution of 2-amino-3-bromo-5-nitro-phenol (6.50 g, 27.89 mmol) in EtOH (150.0 mL) was added concentrated H2SO4 (9.40 mL, 177.13 mmol) portion wise. The reaction mixture was then heated to 5O0C followed by portion wise addition of NaNO2 (6.19 g, 89.82 mmol). The resulting solution was refluxed at 8O0C for 2 h. The reaction mixture was then diluted with water and extracted with EtOAc (3 x 150.0 mL). The combined organics was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude was purified over silica gel (100-200 M, 10percent EtOAc-Hexane) to get the desired product (5.0 g, 82percent).1H-NMR (400 MHz, DMSO-d6): delta 7.37 (s, 1 H), 7.53 (s, 1 H), 7.77 (s, 1 H) and 10.91 (s, 1 H).
With sulfuric acid; sodium nitrite; In ethanol; at -10 - 55℃; To a cooled solution (-10° C.) of 2-amino-3-bromo-5-nitro-phenol (643 g, 2.76 mol) in EtOH (13 L) was added conc. H2SO4 (515 mL, 9.97 mol) over a period of 35 min at -10 to -2° C. The reaction mixture was allowed to warm to rt then heated to 50-55° C. followed by portion-wise addition of NaNO2 (671 g, 9.72 mol) over 30 min then heated at reflux for 3 h. After completion of reaction (by TLC), the mixture was concentrated to 3 L and cooled to 0° C. followed by the addition of chilled water (5 L) and extraction with EtOAc (3.x.6 L). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give a semi-solid residue. The residue was treated with 25percent ether-hexane mixture (6 L) and stirred for 1 h. The solid was filtered and washed with hexane (3 L) to obtain the desired product (505 g, 84percent).

 

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