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[ CAS No. 80194-69-0 ]

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2D
Chemical Structure| 80194-69-0
Chemical Structure| 80194-69-0
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Product Details of [ 80194-69-0 ]

CAS No. :80194-69-0MDL No. :MFCD04113632
Formula : C7H4F3NO2 Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :191.11Pubchem ID :10910349
Synonyms :

Computed Properties of [ 80194-69-0 ]

TPSA : 50.2 H-Bond Acceptor Count : 6
XLogP3 : 1.6 H-Bond Donor Count : 1
SP3 : 0.14 Rotatable Bond Count : 1

Safety of [ 80194-69-0 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 80194-69-0 ]

  • Upstream synthesis route of [ 80194-69-0 ]
  • Downstream synthetic route of [ 80194-69-0 ]

[ 80194-69-0 ] Synthesis Path-Upstream   1~11

  • 1
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YieldReaction ConditionsOperation in experiment
0.12 g
Stage #1: With triethylamine In tetrahydrofuran at 0℃; for 0.166667 h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 1 h;
A solution of 728 5-(trifluoromethyl)pyridine-2-carboxylic acid (0.19 g, 1.0 mmol) in 20tetrahydrofuran (10 mL) was cooled to 0° C., 14 triethylamine (0.18 mL, 1.3 mmol) and 126 ethylchloroformate (0.11 mL, 1.1 mmol) were added and the mixture was stirred for 10 min. The reaction mixturewas filtered, to the filtrate were added 49 sodium tetrahydroborate (49 mg, 1.3 mmol) and one piece of ice,and the mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added aqueous sodium hydroxidesolution and the mixture was stirred for 30 min, and extracted with dichloromethane. The organic layer waswashed with water, dried over sodium sulfate, and the desiccant was filtered off. The solvent was evaporatedto give the 729 title compound as a crudely purified product (0.12 g) MS (ESI) m/z 178 (M+H)+
Reference: [1] Patent: US2016/332999, 2016, A1, . Location in patent: Paragraph 0890; 0891
  • 2
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 52334-81-3 ]
  • [ 124236-37-9 ]
  • [ 80194-69-0 ]
YieldReaction ConditionsOperation in experiment
79% at 120℃; for 3 h; Autoclave Reference Example 2 (0150) Production Method of 5-(trifluoromethyl)pyridine-2-carboxylic acid ester (0151) A 100-mL autoclave was charged successively with 2-chloro-5-(trifluoromethyl)pyridine (24.55 g, 135.26 mmol), PdCl2(PPh3)2 (474 mg, 0.5 mol percent), diphenylphosphinobutane (DPPB, 1.45 g, 2.5 mol percent), triethylamine (24 mL) and methanol (50 mL). The atmosphere in the reaction system was replaced by carbon monoxide 3 times. After charging with carbon monoxide to a pressure of 3 atmospheres, the mixture in the autoclave was stirred under heating at 120° C. for 3 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture, and extraction was repeated about 3 times, followed by drying and concentration. The concentrate was subjected to column chromatography (from hexane: ethyl acetate=5:1 to ethyl acetate) to give a methyl ester compound (21.8 g, 79percent) and a carboxylic acid compound (3.86 g, 15percent).
Reference: [1] Patent: US2016/366884, 2016, A1, . Location in patent: Paragraph 0150; 0151
  • 3
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Reference: [1] Patent: US4367336, 1983, A,
[2] Patent: US2006/9456, 2006, A1, . Location in patent: Page/Page column 53
  • 4
  • [ 124-38-9 ]
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Reference: [1] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568
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Reference: [1] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568
  • 6
  • [ 50488-42-1 ]
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Reference: [1] Patent: US4367336, 1983, A,
  • 7
  • [ 52334-81-3 ]
  • [ 80194-69-0 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568
[2] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568
  • 8
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 52334-81-3 ]
  • [ 124236-37-9 ]
  • [ 80194-69-0 ]
YieldReaction ConditionsOperation in experiment
79% at 120℃; for 3 h; Autoclave Reference Example 2 (0150) Production Method of 5-(trifluoromethyl)pyridine-2-carboxylic acid ester (0151) A 100-mL autoclave was charged successively with 2-chloro-5-(trifluoromethyl)pyridine (24.55 g, 135.26 mmol), PdCl2(PPh3)2 (474 mg, 0.5 mol percent), diphenylphosphinobutane (DPPB, 1.45 g, 2.5 mol percent), triethylamine (24 mL) and methanol (50 mL). The atmosphere in the reaction system was replaced by carbon monoxide 3 times. After charging with carbon monoxide to a pressure of 3 atmospheres, the mixture in the autoclave was stirred under heating at 120° C. for 3 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture, and extraction was repeated about 3 times, followed by drying and concentration. The concentrate was subjected to column chromatography (from hexane: ethyl acetate=5:1 to ethyl acetate) to give a methyl ester compound (21.8 g, 79percent) and a carboxylic acid compound (3.86 g, 15percent).
Reference: [1] Patent: US2016/366884, 2016, A1, . Location in patent: Paragraph 0150; 0151
  • 9
  • [ 67-56-1 ]
  • [ 80194-69-0 ]
  • [ 124236-37-9 ]
YieldReaction ConditionsOperation in experiment
84% Reflux A solution of 5-(trifluoromethyl)-pyridine-2-carboxylic acid (CAN 80194-69-0, 3 g, 15.7 mmol) and sulfurous dichloride (0.1 mL) in methanol (30 mL) was stirred under reflux conditions overnight. Removal of the solvent provided the crude title compound which was purified by column chromatography (silica gel, 20 g, 10percent ethyl acetate in petroleum ether) to obtain the title compound (2.7 g, 84percent) as white solid; MS (EI): m/e=206.1 [M+H]+.
84% Reflux A solution of 5-(trifluoromethyl)-pyridine-2-carboxylic acid (CAN 80194-69-0, 3 g, 15.7 mmol) and sulfurous dichloride (0.1 mL) in methanol (30 mL) was stirred under reflux conditions overnight. Removal of the solvent provided the crude title compound which was purified by column chromatography (silica gel, 20 g, 10percent ethyl acetate in petroleum ether) to obtain the title compound (2.7 g, 84percent) as white solid; MS (EI): m/e = 206.1 [M+H]+.
84% Reflux a) 5- (Trifluoromethyl)-pyridine-2-carboxylic acid methyl ester A solution of 5-(trifluoromethyl)-pyridine-2-carboxylic acid (CAN 80194-69-0, 3 g, 15.7 mmol) and sulfurous dichloride (0.1 mL) in methanol (30 mL) was stirred under reflux conditions overnight. Removal of the solvent provided the crude title compound which5 was purified by column chromatography (silica gel, 20 g, 10percent ethyl acetate in petroleum ether) to obtain the title compound (2.7 g, 84percent) as white solid; MS (El): mle = 206.1 [MHi.
80% for 18 h; Inert atmosphere; Reflux [00172] 50C12 (1.1 mL, 15.7 mmol) was added dropwise slowly to a solution of acid 55 (0.6 g, 3.1 mmol) in anhydrous methanol (40 mL). The mixture was stirred at reflux under N2 for 18 h. The solvent was removed under reduced pressure. Water (5 mL) and EtOAc (5 mL) were added to the mixture. The mixture was basified with sat. NaHCO3 solution to pH =7-8. After partition, the aqueous layer was extracted with EtOAc (3 X 3 mL), the combined organic layers were washed with brine (5 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 56 (510 mg, 80percent) as a pale yellow solid, which was used for the next step directly without further purification.

Reference: [1] Patent: US2012/316147, 2012, A1, . Location in patent: Page/Page column 76
[2] Patent: WO2012/168350, 2012, A1, . Location in patent: Page/Page column 158; 159
[3] Patent: WO2014/86705, 2014, A1, . Location in patent: Page/Page column 61; 62
[4] Patent: WO2014/179564, 2014, A1, . Location in patent: Paragraph 00172
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Reference: [1] Patent: WO2017/200863, 2017, A1, . Location in patent: Page/Page column 34
  • 11
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  • [ 1211518-35-2 ]
Reference: [1] Patent: US2012/316147, 2012, A1,
[2] Patent: WO2012/168350, 2012, A1,
[3] Patent: WO2014/86705, 2014, A1,
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