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Structure of 13600-43-6

Chemical Structure| 13600-43-6

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Product Details of [ 13600-43-6 ]

CAS No. :13600-43-6
Formula : C7H3F3N2
M.W : 172.11
SMILES Code : FC(C1=CC=NC=C1C#N)(F)F
MDL No. :MFCD00153107
InChI Key :DHIRCRHQLUNYDS-UHFFFAOYSA-N
Pubchem ID :2736743

Safety of [ 13600-43-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332
Precautionary Statements:P280

Application In Synthesis of [ 13600-43-6 ]

* 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 [ 13600-43-6 ]
  • Downstream synthetic route of [ 13600-43-6 ]

[ 13600-43-6 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 533932-97-7 ]
  • [ 533932-96-6 ]
  • [ 13600-43-6 ]
YieldReaction ConditionsOperation in experiment
56.5% With sodium methylate In methanol at 20℃; for 2 h; Heating / reflux (Reference Example 5)
3-Cyano-4-trifluoromethylpyridine (Compound VIIb, Step F)
To a solution of 28percent sodium methoxide (580 mg, 3.0 mmol), a solution prepared by dissolving 3-[(4,4,4-trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile (a mixture of IIa and IIb; 380 mg, 2.0 mmol) in methanol (5 ml) was added at room temperature and then, the mixture was refluxed for 2 hours..
The reaction solution was poured into water and extracted with ethyl acetate..
The organic layers were combined, washed with brine, dried over magnesium sulfate and then concentrated..
The resulting residue was purified by silica gel column chromatography (a eluding solvent: hexane/ethyl acetate=3/1) to obtain 195 mg (yield 56.5percent) of the title compound.1H-NMR spectrum (200 MHz, CD3OD) δ (ppm) 9.11 (1H, s), 9.03 (1H, d, J=5.1Hz), 7.72 (1H, d, J=5.1Hz).
32.7% With potassium carbonate In methanol for 2 h; Heating / reflux (Reference Example 13)
3-Cyano-4-trifluoromethylpyridine (Compound VIIb, Step F)
3-[(4,4,4-Trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile (a mixture of IIa and IIb; 1.90 g, 10 mmol) was dissolved in methanol (20 ml), and potassium carbonate (2.10 g, 15 mmol) was added..
The mixture was heated under reflux for 2 hours..
The reaction solution was concentrated under reduced pressure..
The resulting residue was purified by silica gel column chromatography (a eluding solvent: hexane/ethyl acetate=3/1) to obtain 653 mg (yield 32.7percent) of the title compound.
References: [1] Patent: EP1460071, 2004, A1, . Location in patent: Page 39.
[2] Patent: EP1460071, 2004, A1, . Location in patent: Page 40.
  • 2
  • [ 533932-97-7 ]
  • [ 13600-43-6 ]
YieldReaction ConditionsOperation in experiment
47.2% With sodium methylate In methanol at 20℃; for 2 h; Heating / reflux (Reference Example 7)
3-Cyano-4-trifluoromethylpyridine (Compound VIIb, Step F)
To a solution of 28percent sodium methoxide (290 mg, 1.5 mmol), a solution prepared by dissolving 3-[(4,4,4-trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile (a high-polar compound IIb; 190 mg, 1.0 mmol) in methanol (2 ml) was added at room temperature and then, the mixture was refluxed for 2 hours..
The reaction solution was poured into water and extracted with ethyl acetate..
The organic layers were combined, washed with brine, dried over magnesium sulfate and then concentrated..
The resulting residue was purified by thin layer chromatography (a developing solvent: hexane/ethyl acetate=3/1) to obtain 81.0 mg (yield 47.2percent) of the title compound.
References: [1] Patent: EP1460071, 2004, A1, . Location in patent: Page 39.
  • 3
  • [ 533932-96-6 ]
  • [ 13600-43-6 ]
YieldReaction ConditionsOperation in experiment
41.5% With sodium methylate In methanol at 20℃; for 2 h; Heating / reflux (Reference Example 6)
3-Cyano-4-trifluoromethylpyridine (Compound VIIb, Step F)
To a solution of 28percent sodium methoxide (290 mg, 1.5 mmol), a solution prepared by dissolving 3-[(4,4,4-trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile (a low-polar compound IIa; 190 mg, 1.0 mmol) in methanol (2 ml) was added at room temperature and then, the mixture was refluxed for 2 hours..
The reaction solution was poured into water and extracted with ethyl acetate..
The organic layers were combined, washed with brine, dried over magnesium sulfate and then concentrated..
The resulting residue was purified by thin layer chromatography (a developing solvent: hexane/ethyl acetate=3/1) to obtain 71.0 mg (yield 41.5percent) of the title compound.
References: [1] Patent: EP1460071, 2004, A1, . Location in patent: Page 39.
  • 4
  • [ 13600-42-5 ]
  • [ 13600-43-6 ]
YieldReaction ConditionsOperation in experiment
95.22% With palladium on activated carbon; hydrogen; triethylamine In tetrahydrofuran for 4 h; 10 wtpercent Pd/C, 100 g (988 mmol) Et3N, 100 g (415 mmol) 2,6-dichloro-3-cyano-4-trifluoromethylpyridine, 1 L THF were added to a 5 L reaction flask, and the reaction flask was replaced with hydrogen three times. The reaction was stirred for 4 hours, and the solid material in the reaction vessel was collected by filtration, and the filtered liquid was distilled under reduced pressure to give 68 g (395 mmol) of 3-cyano-4-trifluoromethylpyridine liquid, yield 95.22percent.
References: [1] Patent: CN108191749, 2018, A, . Location in patent: Paragraph 0029; 0052; 0056; 0072; 0078.
  • 5
  • [ 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.
  • 6
  • [ 81290-20-2 ]
  • [ 13600-43-6 ]
  • [ 216431-85-5 ]
References: [1] Journal of the American Chemical Society, 2016, vol. 138, # 19, p. 6103 - 6106.
  • 7
  • [ 154237-70-4 ]
  • [ 13600-43-6 ]
References: [1] Organic Letters, 2014, vol. 16, # 6, p. 1744 - 1747.
  • 8
  • [ 100-54-9 ]
  • [ 13600-43-6 ]
  • [ 216431-85-5 ]
References: [1] Journal of the American Chemical Society, 2016, vol. 138, # 19, p. 6103 - 6106.
 

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