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Chemical Structure| 66146-33-6 Chemical Structure| 66146-33-6

Structure of 66146-33-6

Chemical Structure| 66146-33-6

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Product Details of [ 66146-33-6 ]

CAS No. :66146-33-6
Formula : C8H7NO3
M.W : 165.15
SMILES Code : O=CCC1=CC=CC([N+]([O-])=O)=C1
MDL No. :MFCD06738719

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Application In Synthesis of [ 66146-33-6 ]

* 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 [ 66146-33-6 ]

[ 66146-33-6 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 52022-77-2 ]
  • [ 87413-09-0 ]
  • [ 66146-33-6 ]
YieldReaction ConditionsOperation in experiment
100 mg (100%) With sodium hydrogencarbonate; sodium sulfite; In diethyl ether; dichloromethane; Example 16 5-(3-Nitro-phenyl)-2-(oxalyl-amino)-thiophene-3-carboxylic acid; To <strong>[52022-77-2]3-nitrophenethyl alcohol</strong> (102 mg, 0.61 mmol) in dichloromethane (2.2 ml) at room temperature under nitrogen was added a solution of Dess-Martin periodinane reagent (285 mg, 0.67 mmol) in dichloromethane (2.7 ml). The reaction was stirred at room temperature under nitrogen for 45 minutes, at which time TLC analysis (hexane/ethyl acetate, 50/50) indicated the reaction was complete. Diethyl ether (5.0 ml) was added followed by a solution of 10% sodium sulfite/saturated sodium bicarbonate (5.0 ml, 1:1). The emulsion gradually turned to a clear heterogeneous solution after standing for 10 minutes. Additional dichloromethane was added and the organic phase was washed with water (5 ml), dried (MgSO4), filtered and evaporated in vacuo which afforded 100 mg (100%) of 3-nitrophenyl-acetaldehyde as a clear oil. The aldehyde was used without further purification in the next step. 1H NMR (400 MHz, CDCl3) delta 3.90 (s, 2H), 7.65 (d, 2H), 8.20 (s, 1H), 8.25 (m, 1H), 9.90 (s, 1H).
  • 2
  • [ 52022-77-2 ]
  • [ 87413-09-0 ]
  • 5-(3-Nitro-phenyl)-2-(oxalyl-amino)-thiophene-3-carboxylic acid [ No CAS ]
  • [ 66146-33-6 ]
YieldReaction ConditionsOperation in experiment
100 mg (100%) With sodium hydrogencarbonate; sodium sulfite; In diethyl ether; dichloromethane; Example 16 5-(3-Nitro-phenyl)-2-(oxalyl-amino)-thiophene-3-carboxylic acid To <strong>[52022-77-2]3-nitrophenethyl alcohol</strong> (102 mg, 0.61 mmol) in dichloromethane (2.2 ml) at room temperature under nitrogen was added a solution of Dess-Martin periodinane reagent (285 mg, 0.67 mmol) in dichloromethane (2.7 ml). The reaction was stirred at room temperature under nitrogen for 45 minutes, at which time TLC analysis (hexane/ethyl acetate, 50/50) indicated the reaction was complete. Diethyl ether (5.0 ml) was added followed by a solution of 10% sodium sulfite/saturated sodium bicarbonate (5.0 ml, 1:1). The emulsion gradually turned to a clear heterogeneous solution after standing for 10 minutes. Additional dichloromethane was added and the organic phase was washed with water (5 ml), dried (MgSO4), filtered and evaporated in vacuo which afforded 100 mg (100%) of 3-nitrophenyl-acetaldehyde as a clear oil. The aldehyde was used without further purification in the next step. 1H NMR (400 MHz, CDCl3) delta3.90 (s, 2H), 7.65 (d, 2H), 8.20 (s, 1H), 8.25 (m, 1H), 9.90 (s, 1H).
  • 3
  • [ 52022-77-2 ]
  • [ 61717-82-6 ]
  • [ 66146-33-6 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; Step 1 (3-Nitrophenyl)acetaldehyde A mixture of 10 g of <strong>[52022-77-2]2-(3-nitrophenyl)ethanol</strong>, 25.1 g of 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide and 300 ml of tetrahydrofuran is heated at reflux for 6 hours. After filtration and concentration of the solvent, the product is used as it is in the following Step.
  • 4
  • [ 304-91-6 ]
  • [ 52022-77-2 ]
  • [ 66146-33-6 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; PREPARATION A: 3-Nitrophenylacetaldehyde 90 mmol of iodoxybenzoic acid are added to 60 mmol of <strong>[52022-77-2]2-(3-nitrophenyl)ethanol</strong> in 300 ml of tetrahydrofuran. The reaction mixture is heated at reflux for 4 hours, then cooled and filtered. The filtrate is concentrated to yield the expected compound.
 

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