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Chemical Structure| 120417-45-0 Chemical Structure| 120417-45-0

Structure of 120417-45-0

Chemical Structure| 120417-45-0

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Product Details of [ 120417-45-0 ]

CAS No. :120417-45-0
Formula : C4H4F3NO
M.W : 139.08
SMILES Code : O=C(C(F)(F)F)/C=C\N
MDL No. :MFCD09998090

Safety of [ 120417-45-0 ]

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

Application In Synthesis of [ 120417-45-0 ]

* 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 [ 120417-45-0 ]

[ 120417-45-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 32249-35-7 ]
  • [ 120417-45-0 ]
  • [ 917396-33-9 ]
YieldReaction ConditionsOperation in experiment
Preparation of Reagent 3-(chloromethyl)-2-cyclopropyl-6-(trifluoromethyl)pyridine; A. Preparation of methyl 2-cyclopropyl-6-(trifluoromethyl)nicotinate; To a stirring solution of (Z)-4-amino-1,1,1-trifluorobut-3-en-2-one (3 g, 21.58 mmol) and <strong>[32249-35-7]methyl 3-cyclopropyl-3-oxopropanoate</strong> (3.7 g, 26.03 mmol) in toluene (20 mL) at room temperature under argon was added TFA (2.96 g, 25.92 mmol). The reaction mixture was stirred at reflux for 10 h. The reaction mixture was then cooled to room temperature and concentrated under vacuum to obtain a gum. EtOAc (50 mL) and 15% aqueous sodium carbonate solution (50 mL) were added, and the resulting mixture was stirred at room temperature for 10 min. The organic layer was separated, washed with saturated aqueous NaCl, dried (MgSO4), filtered and concentrated to obtain crude product as a yellow oil. This crude product was purified by automated silica gel chromatography (eluted with ethyl acetate-hexanes) to isolate 1 g of the title compound as a pale yellow oil. HPLC/MS: retention time=3.618 min, [M+H]30 =246.
A. Preparation of methyl 2-cyclopropyl-6-(trifluoromethyl)nicotinate To a stirring solution of (Z)-4-amino-1,1,1-trifluorobut-3-en-2-one (3 g, 21.58 mmol) and <strong>[32249-35-7]methyl 3-cyclopropyl-3-oxopropanoate</strong> (3.7 g, 26.03 mmol) in toluene (20 mL) at room temperature under argon was added TFA (2.96 g, 25.92 mmol). The reaction mixture was stirred at reflux for 10 h. The reaction mixture was then cooled to room temperature and concentrated under vacuum to obtain a gum. EtOAc (50 mL) and 15% aqueous sodium carbonate solution (50 mL) were added, and the resulting mixture was stirred at room temperature for 10 min. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated to obtain crude product as a yellow oil. This crude product was purified by automated silica gel chromatography (eluted with ethyl acetate-hexanes) to isolate 1 g of the title compound as a pale yellow oil. HPLC/MS: retention time=3.618 min, [M+H]+=246.
  • 2
  • [ 34846-90-7 ]
  • [ 120417-45-0 ]
  • [ 186273-73-4 ]
YieldReaction ConditionsOperation in experiment
88.3% With sodium hydride; In N,N-dimethyl-formamide; at -15 - -10℃; for 3h;Inert atmosphere; Under nitrogen protection, add 12.9g (323.5mmol) of NaH and 150g of DMF to the reaction flask at -15-10°C.4-amino-1,1,1-trifluoro-3-buten-2-one50 g (359.5 mmol) solution, the system turned from colorless to light yellow and finally to a red suspension,Methyl 3-methoxyacrylate (41.75 g, 359.5 mmol) was added dropwise and reacted at this temperature for 3 hours.Concentrated hydrochloric acid was added dropwise to the reaction flask at -10°C to adjust the pH of 8-9. The system changed from a deep red suspension to orange, and water was added.1.5L of dilute hydrochloric acid was used to adjust the pH to 1 to 2, and a large amount of white flocculent solids precipitated. After stirring for 0.5 hours, 81.5 g of a white product was obtained by filtration (yield, 88.3percent).The NMR analysis of the product obtained in this example is shown in Figure 1.Prove that the resulting product isN-1-methoxy-2-methoxycarbonylethyl-4,4,4-trifluoro-3-keto-1-butenamine..
  • 3
  • [ 34846-90-7 ]
  • [ 120417-45-0 ]
  • N-(2-methoxycarbonylvinyl)-4,4,4-trifluoro-3-oxo-1-butenamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Alkaline conditions; In the process of synthesizing the flonicamidamide intermediate by the above formula,The impurity 2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)benzene-1,3,5-tricarboxylic acid methyl ester appeared.The presence of impurities not only affects the quality of the intermediates and final products, but also greatly reduces the yield of the reaction.Methyl 2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)benzene-1,3,5-tricarboxylate prepared in Examples 1-9 in this example Provides an application,That is, it can be used as a standard control to detect the presence or absence of flonicamid and its intermediate N-(2-methoxycarbonylvinyl)-4,4,4-trifluoro-3-one-1-butenamine Methyl (1,3-dimethoxy-3-oxoprop-1-en-2-yl)benzene-1,3,5-tricarboxylate and its content.In addition, the synthesis of flonicamid intermediates by the above methodin the process of,It can be used as a standard to detect and monitor the formation of this impurity, which is important for optimizing the reaction conditions.
 

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