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[ CAS No. 457097-93-7 ]

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2D
Chemical Structure| 457097-93-7
Chemical Structure| 457097-93-7
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SDS

Product Details of [ 457097-93-7 ]

CAS No. :457097-93-7MDL No. :MFCD15527567
Formula : C9H8F3NO3 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :235.16Pubchem ID :53419671
Synonyms :

Computed Properties of [ 457097-93-7 ]

TPSA : 61.6 H-Bond Acceptor Count : 7
XLogP3 : 2.3 H-Bond Donor Count : 1
SP3 : 0.22 Rotatable Bond Count : 3

Safety of [ 457097-93-7 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 457097-93-7 ]

  • Upstream synthesis route of [ 457097-93-7 ]
  • Downstream synthetic route of [ 457097-93-7 ]

[ 457097-93-7 ] Synthesis Path-Upstream   1~4

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YieldReaction ConditionsOperation in experiment
96.2%
Stage #1: at -5 - -4℃; for 1.00 h;
Stage #2: at 15 - 30℃; for 72.00 h;
Thionyl chloride (2.68g, 0.023 mol) was added dropwise to methanol (12 mL) at -5° C via a syringe keeping the temperature at or below -4° C. The resulting mixture was stirred at or below -5° C for 1 hr., then 4-amino- 3-(trifluoromethoxy)benzoic acid (0.5g, 0.003 mol) [Alfa Aesar] was added in one portion. The reaction mixture was stirred at ambient temperature for 3 days after which the mixture was concentrated in vacuo. Water (10 mL) was added to the residue and sodium bicarbonate (0.46g, 5.4 mmol) was added in one portion and the mixture was stirred at ambient temperature for 30 min. The mixture was extracted several times with ethyl acetate. The combined organic phase was dried over sodium sulfate, filtered and concentrated in vacuo to give 1.02g (96.2percent) of methyl 4-amino-3-(trifiuoromethoxy)berrzoate as a red oil that slowly sodified to a brown solid on cooling. MS: m/z 236.1 (MH+). 1H NMR (500 MHz, DMSO-d6): δ 3.771 (s, 3H), 6.329 (s, 2H), 6.834 (d, 1H), 7.6181 (s, 1H), 7.655 (dd, 1H).
95% With hydrogenchloride In 1,4-dioxane at 20℃; for 72.00 h; A.
Methyl 4-amino-3-(trifluoromethoxy)benzoate
A mixture of 4-amino-3-(trifluoromethoxy)benzoic acid (8.88 g 40.2 mmol), MeOH (142 mL) and hydrochloric acid in 1,4-dioxane (4.0 M, 142 mL, 568 mmol) was stirred at room temperature for 72 h.
After removal of the organic solvent the pH of the residue was adjusted to pH 8 and the aqueous layer was extracted with ethyl acetate (50 mL*3).
The combined organic layers were dried and concentrated under vacuum to afford the title compound (9.3 g, 39.6 mmol, 95percent yield). MS (ESI) m/z 236.1 [M+1]+.
Reference: [1] Patent: WO2014/165816, 2014, A1. Location in patent: Page/Page column 92
[2] Patent: US2015/175557, 2015, A1. Location in patent: Paragraph 0300
[3] Patent: EP2017263, 2009, A1. Location in patent: Page/Page column 213
[4] Patent: US2013/115194, 2013, A1. Location in patent: Paragraph 0335
[5] Patent: US2013/287731, 2013, A1. Location in patent: Paragraph 0284; 0285
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  • [ 201230-82-2 ]
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YieldReaction ConditionsOperation in experiment
54% at 100℃; for 36.00 h; To a solution of 4-bromo-2-(trifluoromethoxy)aniline (10 g, 50.21 mmol) in methanol (150 mL) in a pressure tank reactor was added TEA (11.84 g, 117.01 mmol), Pd(dppf)Ci2 CH2Q2 (2.4 g, 2.94 mmol). Then the reactor was charged with CO (g) (20 atm). The resulting reaction was stirred for 1.5 days at 100°C. Then it was diluted with water (200 mL), extracted with ethyl acetate (3 x 100 mL) and the organic layers combined and dried in an oven under reduced pressure. The resulting mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1 :50) to afford methyl 4- amino-3-(trifluoromethoxy)benzoate as yellow solid (5 g, 54percent).
Reference: [1] Patent: WO2014/66795, 2014, A1. Location in patent: Paragraph 0175
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Reference: [1] Patent: US2012/114600, 2012, A1
  • 4
  • [ 175278-22-5 ]
  • [ 186581-53-3 ]
  • [ 457097-93-7 ]
Reference: [1] Patent: US2003/69284, 2003, A1
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