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Structure of 3314-35-0

Chemical Structure| 3314-35-0

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Product Details of [ 3314-35-0 ]

CAS No. :3314-35-0
Formula : C9H11N3
M.W : 161.20
SMILES Code : NC1=NN(C2=CC=CC=C2)CC1
MDL No. :MFCD00051730

Safety of [ 3314-35-0 ]

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

Application In Synthesis of [ 3314-35-0 ]

* 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 [ 3314-35-0 ]

[ 3314-35-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 3314-35-0 ]
  • [ 1128-56-9 ]
YieldReaction ConditionsOperation in experiment
80% copper(l) chloride; In ethanol; EXAMPLE 2 Using the same apparatus as in Example 1 and following the same modalities, 5 g (0.031 mole) of 1-phenyl-3-amino-2-pyrazoline were suspended in 25 ml of ethanol with the addition of 0.1 g (0.001 mole) of CuCl and of 0.064 g (0.001 mole) of metallic Cu, under an oxygen head, at a temperature of 30 C. After about 2 hours, the oxidation was completed and the whole solid was dissolved. The catalyst was filtered and, after removal of the solvent under vacuum, 1-phenyl-3-aminopyrazole (I) was hot extracted with diluted HCl from which, after clarification with animal charcoal, 4 g of product (I) precipitated in the form of whitish needles by neutralization with aqueous NaOH. The melting point of the product was 89-90 C.; the yield was about 80% of the theoretical value.
41% With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20℃; for 1h; To a solution of 1-phenyl-3-amino-pyrazoline(7.4 g, 46 mmol) in dioxane (200 mL) was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (11.54 g, 50 mmol). After addition, the reaction was stirred at RT for 1 hour, then the resulting dark solution was filtered through a pad of Celite. The filtrate was acidified with 1N aqueous HCl (100 mL) and extracted with CH2Cl2 (50 mL). The organic layer was extracted with 1N aqueous HCl (50 mL). The combined aqueous layers were washed with CH2Cl2 (2×50 mL), then adjusted to pH12 with NaOH, followed by extraction with CH2Cl2 (3×100 mL). The combined CH2Cl2 extracts were washed with saturated NaCl (100 mL), dried (MgSO4), and concentrated under reduced pressure to give the title compound, 1-phenyl-3-amino-pyrazole as light orange solid (3.0 g, 41% yield). LC/MS (method A): retention time=1.43 min, (M+H)+=160.
copper(l) chloride; In acetonitrile; EXAMPLE 4 Example 1 was repeated using the following amounts of reagents: 5 g (0.031 mole) of 1-phenyl-3-amino-2-pyrazoline were dissolved in 25 ml of acetonitrile under addition of 0.2 g (0.00201 mole) of CuCl, under an oxygen head. Oxidation lasted about 3 hours. 2.5 g of 1-phenyl-3-aminopyrazole were obtained.
copper(l) chloride; In acetic acid; EXAMPLE 5 Using the same apparatus as in Example 1 and following the same modalites, 5 g (0.031 mole) of 1-phenyl-3-amino-2-pyrazoline were dissolved in 15 ml of acetic acid with addition of 0.2 g (0.00201 mole) of CuCl, under an oxygen head. Oxidation was completed after about 5 hours. Acetic acid was neutralized with sodium bicarbonate, it was filtered and the precipitate was extracted with ether. By evaporating the ethereal solution, 1.5 g of 1-phenyl-3-aminopyrazole were obtained.
12.2 g To a solution of 1-phenyl-4,5-dihydro-1H-pyrazol-3-ylamine (50.0 g) in N,N-dimethylformamide (150 ml) and 1,4-dioxane (500 ml) was added 3,4,5,6-tetrachloro-1,4-benzoquinone (84.0 g) under ice-cooling over 20 minutes, and the mixture was stirred at room temperature for 4.5 hours. To the reaction mixture was added a 2M aqueous solution of sodium hydroxide (400 ml) under ice-cooling over 25 minutes, and the mixture was stirred at room temperature for 1 hour. The mixture was filtered through Celite to remove the insoluble substance, and eluted with ethyl acetate (250 ml*3), and then the filtrate was extracted with ethyl acetate (300 ml). The resulting organic layer was sequentially washed with water (300 ml) and a saturated aqueous solution of sodium chloride (300 ml). The separated aqueous layer was extracted twice with ethyl acetate (300 ml). To the combined organic layer were added anhydrous sodium sulfate (50 g) and silica gel (50 g), and the mixture was stirred at room temperature for 1 hour. This mixture was filtered with silica gel (100 g) on Celite, and subjected to elution with ethyl acetate (250 ml*3). The filtrate was concentrated, and diisopropyl ether (500 ml) was added to the resulting residue, and the mixture was stirred at room temperature. The insoluble substance was collected by filtration, washed twice with diisopropyl ether (100 ml), and dried under reduced pressure to give the titled compound (12.2 g). 1H-NMR (CDCl3) delta: 3.81 (br s, 2H), 5.85 (d, 1H, J=2.4 Hz), 7.16-7.19 (m, 1H), 7.38-7.40 (m, 2H), 7.55-7.57 (m, 2H), 7.69 (d, 1H, J=2.4 Hz).

  • 2
  • [ 3314-35-0 ]
  • [ 15980-22-0 ]
  • [ 133356-67-9 ]
  • 4-(4,5-dihydro-1-phenyl-1H-pyrazol-3-yl)amino-2,6-dimethylphenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; In dichloromethane; Example D 2,6-dimethyl-4-(1-phenyl-1H-pyrazol-3-yl)aminophenol <strong>[15980-22-0]2,6-dimethyl-4-aminophenol</strong> (15 g) and 4,5-dihydro-1-phenyl-1H-pyrazol-3-amine (17.6 g) were heated with p-toluene sulfonic acid (0.2 g) at 160 for 1 hour under nitrogen. The mix was cooled, taken up in dichloromethane and washed with dilute HCl, and water. Evaporation, and chromatography of the residue (silica, dichloromethane/ethyl acetate [9:1]) gave 4-(4,5-dihydro-1-phenyl-1H-pyrazol-3-yl)amino-2,6-dimethylphenol (14.2 g), mp 154-158. This was refluxed in toluene (40 ml) with 10% palladium on charcoal (10 g) for 3 hours. The mixture was filtered and evaporated to give, after crystallisation from cyclohexane/ethyl acetate, the title compound (8 g), mp 154-155.
  • 3
  • [ 3314-35-0 ]
  • [ 7732-18-5 ]
  • [ 1128-56-9 ]
YieldReaction ConditionsOperation in experiment
copper(l) chloride; In ethanol; EXAMPLE 3 Example 1 was repeated using the following amounts of reagents: 5 g (0.031 mole) of 1-phenyl-3-amino-2-pyrazoline were suspended in 25 ml of ethanol and 2 ml of H2 O, under addition of 0.1 g (0.001 mole) of CuCl and 0.064 g (0.001 mole) of Cu, under an oxygen head. Oxidation lasted about 3 hours. 3.9 g of 1-phenyl-3-aminopyrazole were obtained.
 

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