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Chemical Structure| 121247-16-3 Chemical Structure| 121247-16-3

Structure of 121247-16-3

Chemical Structure| 121247-16-3

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Product Details of [ 121247-16-3 ]

CAS No. :121247-16-3
Formula : C9H7F2NO3
M.W : 215.15
SMILES Code : CC(CC1=C([N+]([O-])=O)C=CC(F)=C1F)=O
MDL No. :MFCD07783788

Safety of [ 121247-16-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 121247-16-3 ]

* 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 [ 121247-16-3 ]

[ 121247-16-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 121247-16-3 ]
  • [ 288385-99-9 ]
YieldReaction ConditionsOperation in experiment
71% With potassium carbonate; In methanol; for 3h;Heating / reflux; A mixture of 1-(2,3-difluoro-6-nitrophenyl) -propan-2-one (183 g) and potassium carbonate (100 g) in methanol (1L) was heated at reflux for 3 h. The reaction mixture was then cooled and concentrated in vacuo to remove most of the methanol. The residue was diluted with ethyl acetate (1L), filtered and washed with water. The separated aqueous layer was neutralized with 2N HCl and extracted with ethyl acetate (2x500 mL). The combined organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo to give a brown solid. The solid was triturated with diethyl ether and filtered to provide 1-(2-fluoro-3-methoxy-6-nitrophenyl)-propan-2-one (121 g, 71 %) as a yellow solid. LC/MS; (M+H)+ = 228.2
  • 2
  • [ 121247-16-3 ]
  • [ 649736-31-2 ]
YieldReaction ConditionsOperation in experiment
54% With sodium acetate; In N,N-dimethyl-formamide; at 100℃; for 12.0h; Step 3b: 1-(2-Fluoro-3-hydroxy-6-nitrophenyl)propan-2-one (Compound 303) A mixture of 302 (4.30 g, 0.02 mol), AcONa (1.72 g, 0.021 mol) and DMF (40 mL) was stirred at 100 C. for 12 h. The mixture was then filtered and the solvent was removed under reduced pressure and the residue was extracted with ethyl acetate (100 mL). The organic layer was washed with water, brine, dried over MgSO4 and concentrated. The residue was purified by column chromatography on silica gel (EtOAc/petroleum ether=1/1) to give compound 303 (2.3 g, 54%) as a pale yellow solid: LCMS: 214 [M+1]+; 1H NMR (DMSO-d6): delta 2.30 (s, 3H), 4.26 (s, 2H), 7.67 (m, 1H), 8.05 (m, 1H).
  • 3
  • [ 67-56-1 ]
  • [ 121247-16-3 ]
  • [ 288385-99-9 ]
YieldReaction ConditionsOperation in experiment
Step 3: preparation of 1-(2-fluoro-3-methoxy-6-nitrophenyl)propan-2-one In a 100mL round-bottomed flask 2g 1-(2,3-difluoro-6-nitrophenyl)propan-2-one prepared from Step 2 was added to a solution of sodium methoxide in methanol(40mL), wherein the solution of sodium methoxide in methanol was prepared by slowly adding 2.27g Na to methanol with sitrring in an ice bath and stirring for 1h at 50C after the addition. The mixture was reacted for 1h at room temperature before the reaction was complete, and quenched by adding 1mL water and extracted with dichloromethane. The organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound. 1H NMR(400MHz,DMSO-d6) delta ppm:8.04-8.07(m,1H),7.31-7.35(m,1H),4.20-4.21(d, 2H),3.98(s,3H),2.28(s,3H).
 

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