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Chemical Structure| 1227210-46-9 Chemical Structure| 1227210-46-9

Structure of 1227210-46-9

Chemical Structure| 1227210-46-9

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Product Details of [ 1227210-46-9 ]

CAS No. :1227210-46-9
Formula : C5H7N3O3
M.W : 157.13
SMILES Code : OCC1=CC([N+]([O-])=O)=NN1C
MDL No. :MFCD18262310

Safety of [ 1227210-46-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 1227210-46-9 ]

* 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 [ 1227210-46-9 ]

[ 1227210-46-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 181585-93-3 ]
  • [ 74-88-4 ]
  • [ 1227210-46-9 ]
YieldReaction ConditionsOperation in experiment
To a solution of 2-methyl-<strong>[181585-93-3]5-nitro-2H-pyrazole-3-carboxylic acid methyl ester</strong> and 1-methyl-5-nitro-1H-pyrazole-3-carboxylic acid methyl ester (1.18 g, 6.37 mmol) in tetrahydrofuran (20 mL) at 0 C. was added a lithium aluminum hydride solution (1.0M in tetrahydrofuran, 7.65 mL, 7.65 mmol) drop wise. The resulting mixture was stirred at 0 C. for 20 min. To this solution was added ethyl acetate (1 mL) followed by few crystals of sodium sulphate decahydrate. The resulting mixture was stirred for 30 min then filtered, the filter cake washed with ethyl acetate and the filtrate evaporated. The residue was purified by flash chromatography (silica gel, 80 g, 50% to 70% ethyl acetate in hexanes) to give 1-methyl-3-nitro-1H-pyrazol-5-yl)methanol (496 mg, 50%) as a white solid.
496 mg To a solution of 2-methyl-<strong>[181585-93-3]5-nitro-2H-pyrazole-3-carboxylic acid methyl ester</strong> and 1-methyl-5-nitro-1H-pyrazole-3-carboxylic acid methyl ester (1.18 g, 6.37 mmo 1) in tetrahydro furan (20 mL) at 0C was added a lithium aluminum hydride solution (1 .OM in tetrahydrofuran, 7.65 mL, 7.65 mmol) drop wise. The resulting mixture was stirred at 0C for 20 min. To this solution was added ethyl acetate (1 mL) followed by few crystals of sodium sulphate decahydrate. The resulting mixture was stirred for 30 min then filtered, the filter cake washed with ethyl acetate and the filtrate evaporated. The residue was purified by flash chromatography (silica gel, 80 g, 50% to 70% ethyl acetate in hexanes) to give 1-methyl-3-nitro-1H-pyrazol-5-yl)methanol (496 mg, 50%) as a white solid. 1H NMR (300 MHz, DMSO-d6) delta ppm 3.90 (s, 3 H) 4.53 (d, J=5.67 Hz, 2 H) 5.55 (t, J=5.48 Hz, 1 H) 6.93 (s, 1 H).
  • 2
  • [ 181585-93-3 ]
  • [ 74-88-4 ]
  • [ 1227210-46-9 ]
  • [ 1260659-40-2 ]
YieldReaction ConditionsOperation in experiment
65.7%; 249 mg Step 12: Preparati -Methyl-<strong>[181585-93-3]5-nitro-2H-pyrazole-3-carboxylic acid methyl ester</strong> A 100-mL single-neck round-bottomed flask was charged with methyl 5-nitro-lH-pyrazole-3- carboxylate (3.89 g, 22.7 mmol), anhydrous DMF (30 ml) , potassium carbonate (6.28 g, 45.5 mmol). Mel (4.19 g, 1.85 ml, 29.6 mmol) was added and the reaction mixture was stirred at room temperature for 18h. The mixture was then diluted with water (150 mL) and extracted with DCM (3 x 75mL). The combined organic layers were dried over MgS04 and concentrated under vacuum. The crude material was purified by flash chromatography (silica gel, AnaLogix system, SF40-240g column, 10% to 50% EtOAc in hexanes) to give the desired product as mixture of isomers (3.75 g). M+ = 185.0 m/e Step 13: In a 250 mL three-necked flask equipped with a thermometer and nitrogen inlet, LiBH4 (882 mg, 40.5 mmol) was combined with THF (30mL) to give a white suspension and cooled to 0 C using an ice bath. To this mixture, methyl l-methyl-3-nitro-lH-pyrazole-5-carboxylate (3.75g, 20.3 mmol) dissolved in THF (lOmL) was slowly added keeping the internal temperature at 0 C. After the addition was complete, the cooling bath was removed and the reaction mixture was stirred at room temperature for lh. A few drops of MeOH were then added and the reaction mixture was stirred for 2h. The reaction was cooled to 0 C using an ice bath and EtOAc (20 mL) was added followed by slow addition of water (100 mL). The layers were separated and the aqueous layer was extracted with EtOAc (3 x lOOmL). The combined extracts were washed with brine (100 mL), dried over MgS04 and concentrated under vacuum. The crude material was purified by flash chromatography (silica gel, Analogix system SF40-240g, 30% to 60% EtOAc in hexanes) to give separately the title compound (2.09 g, 65.7 %) and it isomer (249 mg, 7.82 g). (M+H)+ = 157.9 m/e
 

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