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Chemical Structure| 60521-26-8 Chemical Structure| 60521-26-8

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Chemical Structure| 60521-26-8

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Product Details of [ 60521-26-8 ]

CAS No. :60521-26-8
Formula : C15H12O2
M.W : 224.26
SMILES Code : OC(=O)C=CC1=CC=CC(=C1)C1=CC=CC=C1
MDL No. :MFCD09042492

Safety of [ 60521-26-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of [ 60521-26-8 ]

* 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 [ 60521-26-8 ]

[ 60521-26-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 29608-05-7 ]
  • [ 60521-26-8 ]
  • 1-(4-(3-phenylcinnamoylamino)benzyl)piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N-methyl-acetamide; water; WORKING EXAMPLE 81 (Production of Compound 81) To 3-phenylcinnamic acid (0.62 g) were added thionyl chloride (5 ml) and dimethylformamide (catalytic amount), and the mixture was refluxed for 4 hours. The solvent was evaporated, and the residue was dissolved in tetrahydrofuran. The mixture was dropwise added to a suspension of <strong>[29608-05-7]1-(4-aminobenzyl)piperidine</strong> (0.5 g) and diisopropylethylamine (1.2 ml) in tetrahydrofuran (5 ml) under ice-cooling. Under nitrogen atmosphere, the mixture was stirred at room temperature over night. The solvent was evaporated, and to the residue was added water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (methanol/triethylamine/ethyl acetate). The resulting crude crystals was recrystallized from ethyl acetate-hexane to give 1-(4-(3-phenylcinnamoylamino)benzyl)piperidine (Compound 81) (0.45 g) as pale yellow crystals. mp 159-160 C.; 1 H-NMR(delta ppm, CDCl3): 1.37-1.48 (2H, m), 1.49-1.63 (4H, m), 2.34-2.42 (4H, m), 3.45 (2H, s), 6.62 (1H, d, J=15.4 Hz), 7.23-7.63 (13H, m), 7.76 (1H, s), 7.83 (1H, d, J=15.4 Hz). IR(KBr) nu: 2934, 1659, 1624 cm-1. Anal. for C27 H28 N2 O.0.5H2 O: Calcd. C, 79.97; H, 7.21; N, 6.91. Found C, 81.09; H, 7.02; N, 6.94.
  • 2
  • [ 1095-03-0 ]
  • [ 79432-87-4 ]
  • [ 60521-26-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; potassium carbonate;tetrakis(triphenylphosphine)palladium (0); In methanol; ethanol; toluene; REFERENCE EXAMPLE 56 A suspension of methyl 3-bromocinnamate (3.8 g), phenyl borate (2.0 g), 1M potassium carbonate (20 ml) and ethanol (10 ml) in toluene(100 ml) was stirred under argon atmosphere at room temperature for 30 minutes. To the reaction mixture was added tetrakistriphenylphosphinepalladium (0.9 g), and the mixture was refluxed over night and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (ethyl acetate/hexane) to give colorless crystals (3.6 g), 1.8 g of which was dissolved in a solution of methanol (100 ml) and 1N sodium hydroxide (20 ml). The mixture was stirred at room temperature over night, concentrated, neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 3-phenylcinnamic acid (1.5 g) as colorless crystals. 1 H-NMR(delta ppm, CDCl3): 6.54 (1H, d, J=16.0 Hz), 7.39-7.67 (8H, m), 7.76-7.77 (1H,m), 7.87 (1H,d,J=16.0 Hz). IR(KBr) nu 1709 cm-1. Anal. for C15,H12 O2: Calcd. C,80.34; H,5.39. Found C,80.62; H,5.40.
 

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