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Chemical Structure| 290353-57-0 Chemical Structure| 290353-57-0

Structure of 290353-57-0

Chemical Structure| 290353-57-0

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Product Details of [ 290353-57-0 ]

CAS No. :290353-57-0
Formula : C7H5BrN2O4
M.W : 261.03
SMILES Code : O=[N+](C1=CC=C(Br)C(C)=C1[N+]([O-])=O)[O-]
MDL No. :MFCD18642363
InChI Key :OXYXHHOXCIPFBY-UHFFFAOYSA-N
Pubchem ID :15889633

Safety of [ 290353-57-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H303-H315-H319-H228
Precautionary Statements:P240-P210-P241-P264-P280-P302+P352-P370+P378-P312-P337+P313-P305+P351+P338-P362+P364-P332+P313
Class:4.1
UN#:1325
Packing Group:

Application In Synthesis of [ 290353-57-0 ]

* 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 [ 290353-57-0 ]

[ 290353-57-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 122-51-0 ]
  • [ 290353-57-0 ]
  • [ 952511-48-7 ]
YieldReaction ConditionsOperation in experiment
73% To a stirred solution of 1-bromo-2-methyl-3,4-dinitro-benzene (Tetrahedron Lett. 2000, 41(22), 4277-4279) (2.61 g, 10 mmol) in EtOH (50 mL) was added SnCl2 (1.89 g, 100 mmol). The mixture was stirred at 50° C. for 2 h. The mixture was cooled to rt, and triethylorthoformate (25 mL) was added. After heating for 30 min at 70° C., the mixture was cooled to rt, diluted with satd. aq. NaHCO3 (100 mL), and extracted with EtOAc (3.x.60 mL). The combined organic layers were washed with satd. aq. NaCl (100 mL), dried, and concentrated to give a solid residue. The residue was stirred vigorously with MeOH (100 mL) and the precipitate removed by filtration. The filtrate was concentrated to yield the crude product which was then purified by FCC (EtOAc/hexanes) to give 1.55 g (73percent) of the desired product. MS: mass calcd. for C8H7BrN2, 209.98; m/z found, 211.0 [M+H]+. 1H NMR (CD3OD): 8.18 (s, 1H), 7.41 (d, J=8.7 Hz, 1H), 7.34 (d, J=8.6 Hz, 1H), 2.61 (s, 3H).
  • 2
  • [ 290353-57-0 ]
  • [ 952511-74-9 ]
YieldReaction ConditionsOperation in experiment
91% With tin(II) chloride dihdyrate; In ethanol; ethyl acetate; at 80.0℃; for 12.0h; step 2: A mixture of 154 (40 g,154 mmol), SnCl2-2H20 (208 g, 920 mmol), EtOAc (300 mL) and EtOH (150 mL) was heated to 80 °C for 12 h, cooled to RT, poured into crushed ice (2 Kg) and the pH adjusted to pH 7-8 with solid NaHCC>3. The solid was filtered and washed with EtOAc. The filtrate was thrice extracted with EtOAc. The combined extracts were washed with brine, dried (Na2SO (), filtered and concentrated in vacuo. The crude product was purified by Si02 chromatography eluting with an EtOAc/hexane gradient (10 to 50percent EtOAc) to afford 28 g (91percent) of 4-bromo-3 -methyl- 1,2- benzenediamine (156) as a brown oil: MS (ESI) m/z = 202 [M+l]+.
With tin(II) chloride hydrate; In ethanol; ethyl acetate; at 80.0℃; for 12.0h; 1-Bromo-2-methyl-3,4-dinitrobenzene (10.7 g, 0.041 mol), tin(II) chloride hydrate (64.79 g, 0.287 mol), ethyl acetate (128 ml) and ethanol (64 ml) were heated at 80° C. for 12 h, cooled to room temperature, poured onto crushed ice (1000 g) and adjusted with solid sodium bicarbonate to pH 7-8. The solid was removed by filtration and washed with ethyl acetate. The filtrate was extracted with ethyl acetate three times. The combined extracts were washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (10 to 50percent ethyl acetate in hexanes) to give the title compound as a brown oil.1H NMR (400 MHz, CDCl3) delta ppm 2.30 (s, 3H) 3.20-3.40 (br., 4H) 6.48 (d, 1H) 6.90 (d, 1H)
  • 3
  • [ 290353-57-0 ]
  • [ 952511-48-7 ]
 

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