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Chemical Structure| 59938-06-6 Chemical Structure| 59938-06-6

Structure of 59938-06-6

Chemical Structure| 59938-06-6

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Product Details of [ 59938-06-6 ]

CAS No. :59938-06-6
Formula : C6H7F3O2
M.W : 168.11
SMILES Code : O=C(/C=C/OCC)C(F)(F)F
MDL No. :MFCD00192131
InChI Key :YKYIFUROKBDHCY-ONEGZZNKSA-N
Pubchem ID :5709222

Safety of [ 59938-06-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319
Precautionary Statements:P210-P233-P240-P241+P242+P243-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P403+P235-P501
Class:3
UN#:1993
Packing Group:

Application In Synthesis of [ 59938-06-6 ]

* 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.

  • Upstream synthesis route of [ 59938-06-6 ]
  • Downstream synthetic route of [ 59938-06-6 ]

[ 59938-06-6 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 59938-06-6 ]
  • [ 19866-98-9 ]
  • [ 13600-43-6 ]
YieldReaction ConditionsOperation in experiment
96.7%
Stage #1: for 3 h; Reflux; Sealed tube
Stage #2: With sodium ethanolate In ethanol for 5 h; Reflux; Sealed tube
In the 1000 mL sealed four-mouth reaction bottle, the above Example 1 was added.168.1 g of 4-ethoxy-1,1,1-trifluoro-3-en-2-one, 68.1 g of 3-aminoacrylonitrile, and 300 mL of solvent ethanol.Stir well, heat to reflux for 3 hours, then add 59.4 g of sodium ethoxide in ethanol and reflux for 5 hours.Recovery of solvent methanolThe white solid was washed with water to give 166.4 g of 4-trifluoromethylnicotinonitrile in a yield of 96.7percent.
References: [1] Patent: CN109467532, 2019, A, . Location in patent: Paragraph 0028-0033.
  • 2
  • [ 59938-06-6 ]
  • [ 302-15-8 ]
  • [ 154471-65-5 ]
References: [1] Patent: US2016/243100, 2016, A1, . Location in patent: Paragraph 0179-0180.
  • 3
  • [ 59938-06-6 ]
  • [ 60-34-4 ]
  • [ 154471-65-5 ]
References: [1] European Journal of Organic Chemistry, 2002, # 17, p. 2913 - 2920.
[2] Patent: WO2007/43677, 2007, A1, . Location in patent: Page/Page column 485-486.
[3] Patent: US2011/160188, 2011, A1, . Location in patent: Page/Page column 4; 11.
  • 4
  • [ 59938-06-6 ]
  • [ 60-34-4 ]
  • [ 153085-15-5 ]
  • [ 154471-65-5 ]
YieldReaction ConditionsOperation in experiment
24 g at 55℃; for 20 h; Cooling with ice ETFBO (270 g, 1.61 mol, 1.00 eq) was dissolved in methanol (750 mL). The solution was cooled in an ice/water-bath and methyl hydrazine (88.3 mL, 77.7 g, 1.69 mol, 1.05 eq) was added dropwise within 20 minutes. The mixture was heated to 55°C and stirred at this temperature for 20 h in dry air (drying tube). Successively the solvent was removed and the residue distilled under vacuum : 1st Fraction : 150 mbar, 130°C bath temperature, 73~85°C, mixture of isomers, 129 g.2nd Fraction : 70 mbar, 150°C bath temperature, 75~85°C, 1-methyl-3-(trifluoromethyl)-1H-pyrazole, 24 g. Overall yield : 153 g (1.02 mol) 63 percent.
References: [1] Patent: EP2662359, 2013, A1, . Location in patent: Page/Page column 6; 10.
  • 5
  • [ 59938-06-6 ]
  • [ 60-34-4 ]
  • [ 153085-15-5 ]
  • [ 154471-65-5 ]
YieldReaction ConditionsOperation in experiment
24 g at 55℃; for 20 h; Cooling with ice The solution was cooled in an ice/water-bath and methyl hydrazine (88.3 mL, 77.7 g, 1.69 mol, 1.05 eq) was added dropwise within 20 minutes. The mixture was heated to 55°C and stirred at this temperature for 20 h in dry air (drying tube). Successively the solvent was removed and the residue distilled under vacuum : 1st Fraction : 150 mbar, 130°C bath temperature, 73~85°C, mixture of isomers, 129 g. 2nd Fraction : 70 mbar, 150°C bath temperature, 75-85 °C, l-methyl-3-(trifluoro- methyl)-lH-pyrazole, 24 g. Overall yield : 153 g (1.02 mol) 63 percent.
References: [1] Patent: WO2013/167586, 2013, A1, . Location in patent: Page/Page column 10.
  • 6
  • [ 59938-06-6 ]
  • [ 60-34-4 ]
  • [ 154471-65-5 ]
  • [ 272442-83-8 ]
References: [1] Journal of Heterocyclic Chemistry, 2002, vol. 39, # 5, p. 1025 - 1027.
  • 7
  • [ 59938-06-6 ]
  • [ 60-34-4 ]
  • [ 153085-15-5 ]
  • [ 154471-65-5 ]
  • [ 272442-83-8 ]
References: [1] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 6, p. 1087 - 1089.
  • 8
  • [ 59938-06-6 ]
  • [ 123-54-6 ]
  • [ 228572-69-8 ]
YieldReaction ConditionsOperation in experiment
29% With sodium hydride In tetrahydrofuran at 0℃; for 4 h; 4-Ethoxy-1,1, 1-trifluoro-3-buten-2-one (5g, 29.7 mmol) followed by 2,4-pentadione (3. 05ML, 29. 7MMOL) were added to a cooled 0 C suspension of NaH (2.38g, 59.4 mmol) in THF (120 mL). The reaction mixture was REFLUXED for 4 hrs and then partitioned between 1 N HCI and EtOAc. The organic layers were washed with brine, dried over NA2SO4 and concentrated to a red oil. Purification by flash column chromatography (0percent to 10percent EtOAc in hexanes) gave the title compound as a yellow oil (1.73g, 29percent). H NMR (400 MHz, CDC13) : 5 2.69 (s, 3 H), 7.15 (d, J=9.9 Hz, 1 H), 7.25 (s, 1 H), 7.86 (d, J=8.3 Hz, 1 H), 12.29 (s, 1 H).
References: [1] Patent: WO2004/74270, 2004, A2, . Location in patent: Page 192.
[2] Dalton Transactions, 2014, vol. 43, # 10, p. 4127 - 4136.
  • 9
  • [ 59938-06-6 ]
  • [ 123-54-6 ]
  • [ 228572-69-8 ]
References: [1] Synthesis, 1999, # 5, p. 765 - 768.
 

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