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Chemical Structure| 129644-57-1 Chemical Structure| 129644-57-1
Chemical Structure| 129644-57-1

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CAS No.: 129644-57-1

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Product Details of [ 129644-57-1 ]

CAS No. :129644-57-1
Formula : C8H5F3O4
M.W : 222.12
SMILES Code : O=C(O)C1=CC(OC(F)(F)F)=CC=C1O
MDL No. :MFCD01091003
InChI Key :HNYMLXYADOZCNY-UHFFFAOYSA-N
Pubchem ID :2775103

Safety of [ 129644-57-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Application In Synthesis of [ 129644-57-1 ]

* 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 [ 129644-57-1 ]

[ 129644-57-1 ] Synthesis Path-Downstream   1~27

  • 1
  • [ 109-04-6 ]
  • [ 129644-57-1 ]
  • [ 177174-55-9 ]
  • 2
  • [ 124-38-9 ]
  • [ 828-27-3 ]
  • [ 129644-57-1 ]
  • 3
  • [ 108-24-7 ]
  • [ 129644-57-1 ]
  • 2-Acetoxy-5-trifluoromethoxy-benzoic acid [ No CAS ]
  • 4
  • [ 93249-62-8 ]
  • [ 129644-57-1 ]
YieldReaction ConditionsOperation in experiment
91% With sodium hydroxide; silver nitrate; In water; ethyl acetate; Step 1 2-Hydroxy-5-trifluoromethoxy-benzoic Acid To a stirring solution of NaOH (8.15 g, 203.8 mmol) in water (35 mL, 5.8 M) was added an aq solution of silver nitrate (17.3 g, 101.9 mmol, 35 mL water, 2.9 M). A brownish solid formed. The flask was placed in an ice bath and to the stirring suspension was added 2-hydroxy-5-trifluoromethoxy-benzaldehyde in 500 mg portions (10.0 g, 48.5 mmol). After addition was complete and the reaction was stirred for 10 min in an ice bath, the mixture was filtered and the brownish precipitate was washed with hot water. The combined washings were acidified with conc HCl to pH 1 and the precipitate was collected by vacuum filtration. This solid was then dissolved in ethyl acetate. The ethyl acetate was washed with saturated aq NaCl, dried over Na2SO4, and filtered. The aqueous layer was also extracted with ethyl acetate. This organic layer was washed with saturated aq NaCl, dried over Na2SO4, filtered and concentrated to provide 2-hydroxy-5-trifluoromethoxy-benzoic acid (9.8 g, 91%) as a white solid: Rf 0.38 (20% methanol in dichloromethane); 1H NMR (CDCl3, 300 MHz) δ 10.30 (bs, 1H), 7.79 (d, J=3.0 Hz, 1H), 7.41 (dd, J1=9.3 Hz, J2=3.0 Hz, 1H), 7.05 (d, J=9.0 Hz, 1H).
  • 5
  • [ 129644-57-1 ]
  • 2-hydroxy-5-trifluoromethoxy-benzoyl chloride [ No CAS ]
  • 6
  • 2-methoxymethoxy-5-trifluoromethoxy-benzoic acid [ No CAS ]
  • [ 129644-57-1 ]
  • 7
  • [ 828-27-3 ]
  • [ 129644-57-1 ]
  • 8
  • [ 851341-40-7 ]
  • [ 129644-57-1 ]
  • 9
  • [ 129644-57-1 ]
  • 2-hydroxy-<i>N</i>-(3-nitro-benzyl)-5-trifluoromethoxy-benzamide [ No CAS ]
  • 10
  • [ 129644-57-1 ]
  • [2-(3-nitro-benzylcarbamoyl)-4-trifluoromethoxy-phenoxy]-acetic Acid [ No CAS ]
  • 11
  • [ 129644-57-1 ]
  • [2-(3-Nitro-benzylthiocarbamoyl)-4-trifluoromethoxy-phenoxy]-acetic acid [ No CAS ]
  • 12
  • [ 129644-57-1 ]
  • [2-(3-nitro-benzylcarbamoyl)-4-trifluoromethoxy-phenoxy]-acetic acid ethyl ester [ No CAS ]
  • 13
  • [ 129644-57-1 ]
  • [2-(3-nitro-benzylthiocarbamoyl)-4-trifluoromethoxy-phenoxy]-acetic acid ethyl ester [ No CAS ]
  • 14
  • [ 129644-57-1 ]
  • [ 129644-59-3 ]
  • 15
  • [ 129644-57-1 ]
  • [ 142167-26-8 ]
  • 16
  • [ 129644-57-1 ]
  • Acetic acid 2-chlorocarbonyl-4-trifluoromethoxy-phenyl ester [ No CAS ]
  • 18
  • [ 129644-57-1 ]
  • 2-(6-trifluoromethoxy-2,2-dimethyl-2H-1,3-benzoxazin-4-yl)pyridine N-oxide [ No CAS ]
  • 19
  • [ 129644-57-1 ]
  • [ 1026905-12-3 ]
  • 20
  • [ 191604-88-3 ]
  • [ 129644-57-1 ]
YieldReaction ConditionsOperation in experiment
B. Synthesis of 2-Hydroxy-5-trifluoromethoxy-benzoic acid (5-trifluoromethoxy salicylic acid) To a solution of 2-methoxy-5-trifluoromethoxy-benzoic acid (23.6 mg, 0.1 mmol) in anhydrous methylene chloride (0.9 mL) was added, boron tribromide (0.100 mL, 1M solution in methylene chloride) at 0 C. The reaction was allowed to continue for 16 hours. The solution was made acidic (pH=0) using 1N solution of hydrochloric acid, and extracted with ethyl acetate (3*3 ml). The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered and concentrated to give ~11 mg of 2-hydroxy-5-trifluoromethoxy-benzoic acid (5-trifluoromethoxy salicylic acid.
  • 21
  • [ 67-56-1 ]
  • [ 129644-57-1 ]
  • [ 175204-89-4 ]
YieldReaction ConditionsOperation in experiment
100% With sulfuric acid; at 120℃; for 1.0h;Microwave irradiation; A mixture of 2 -hydroxy-5 - (trifluoromethoxy)benzoic acid (300 mg, 1.35 mmol) and a few drops of concentrated H2SO4 was heated to 120 C for 1 h under microwave irradiation, after which LC-MS analysis showed completion. Reaction mixture was concentrated to dryness to afford methyl 2 -hydroxy-5 -(trifluoromethoxy)benzoate (319 mg, 100 % yield) as a white solid, which was used without further purification. NMR (400 MHz, DMSO-ck) d 10.57 (s, 1H), 7.65 (d, J= 3.2 Hz, 1H), 7.54 (dt, J= 9.4, 3.0 Hz, 1H), 7.10 (d, J= 9.1 Hz, 1H), 3.89 (s, 3H). 19F NMR (376 MHz, DMSO-ifc) d -57.17 (s, 3F). LCMS RT (Method 2) = 3.507 min.
100% With sulfuric acid; at 120℃; for 1.0h;Microwave irradiation; A mixture of 2 -hydroxy-5 - (trifluoromethoxy)benzoic acid (300 mg, 1.35 mmol) and a few drops of concentrated H2SO4 was heated to 120 C for 1 h under microwave irradiation, after which LC-MS analysis showed completion. Reaction mixture was concentrated to dryness to afford methyl 2 -hydroxy-5 -(trifluoromethoxy)benzoate (319 mg, 100 % yield) as a white solid, which was used without further purification. NMR (400 MHz, DMSO-ck) d 10.57 (s, 1H), 7.65 (d, J= 3.2 Hz, 1H), 7.54 (dt, J= 9.4, 3.0 Hz, 1H), 7.10 (d, J= 9.1 Hz, 1H), 3.89 (s, 3H). 19F NMR (376 MHz, DMSO-ifc) d -57.17 (s, 3F). LCMS RT (Method 2) = 3.507 min.
97.8% With sulfuric acid;Heating / reflux; Step 3: Preparation of methyl 2-hvdroxy-5-(trifluoromethoxy)benzoate; Concentrated sulfuric acid (1.0 mL) was carefully added to a solution of 2-hydroxy- 5-trifluoromethoxy-benzoic acid (11.0 g, 49.52 mmol) in methanol (150 mL). The mixture was refluxed overnight. Additional sulfuric acid (1.0 mL) was added and the mixture was refluxed for another 3 days. The mixture was cooled to rt, concentrated and purified by a silica gel plug eluting with hexanes. After concentrating the desired fractions, colorless oil was obtained as pure product (11.4 g, 97.8%). 1H NMR (400 MHz, DMSO-d6) δ 10.80 (IH, s), 7.61 (IH, s), 7.44-7.46 (IH, d, J = 8.0 Hz), 7.01-7.03 (IH, d, J = 8.0 Hz), 3.88 (3H, s); LC-MS m/z 234.9 [(M-H)-], HPLC RT (min) 5.05 {method (A)}.
63% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; To a round bottom flask containing a magnetic stir bar was added 2-hydroxy-5- (trifluoromethoxy)benzoic acid (2000.0 mg, 9.00 mmol), followed by CH2CI2(30.0 mL)/MeOH (30.0 mL). Using an ice bath, the mixture was cooled to 0 C while stirring. To this reaction mixture was added EDCI (2590.0 mg, 13.5 mmol, 1.5 eq), followed by DMAP (220.0 mg, 1.80 mmol, 0.2 eq). The reaction temperature was allowed to increase up to room temperature while stirring overnight. Upon completion by LCMS analysis, the reaction mixture was concentrated under reduced pressure. The reaction mixture was partitioned between CH2CI2(30.0 mL) and H2O (20.0 mL). The product was extracted with CH2CI2(3 x 30.0 mL) and the combined organics were dried over Na2S04, filtered, and concentrated under reduced pressure. Purification by ISCO flash chromatography (0- 100% EtOAc in hexanes) afforded methyl 2-hydroxy-5-(trifluoromethoxy)benzoate (1356.1 mg, 5.74 mmol, 63%). LCMS (Method A) tR= 1.62 min, m/z = 237.2 [M+H]+.

  • 22
  • [ 129644-57-1 ]
  • methyl 3-bromo-2-hydroxy-5-(trifluoromethoxy)benzoate [ No CAS ]
  • 23
  • [ 129644-57-1 ]
  • methyl 2-methyl-5-(trifluoromethoxy)-1-benzofuran-7-carboxylate [ No CAS ]
  • 24
  • [ 129644-57-1 ]
  • [ 18107-18-1 ]
  • [ 175204-89-4 ]
YieldReaction ConditionsOperation in experiment
In methanol; dichloromethane; at 0 - 25℃; for 3.0h; a) Methyl 2-hydroxy-5-(trifluoromethoxy)benzoate To a solution of <strong>[129644-57-1]2-hydroxy-5-(trifluoromethoxy)benzoic acid</strong> (2.2 g, 9.90 mmol) in dichloromethane (10 mL) and methanol (2 mL) at 0 C. was added tms-diazomethane (2M) (5 mL) dropwise and the solution was stirred for 3 h at 25 C. The reaction was then quenched by the addition of water. The resulting solution was extracted with DCM (3*10 mL) and the organic layers combined and concentrated under vacuum. The resulting residue was purified on a silica gel column with ethyl acetate/petroleum ether (10/90). The collected fractions were combined and concentrated under vacuum to yield methyl 2-hydroxy-5-(trifluoromethoxy)benzoate as colorless oil.
  • 25
  • [ 129644-57-1 ]
  • methyl 2-(4-bromo-2-nitrophenoxy)-5-(trifluoromethoxy)benzoate [ No CAS ]
  • 26
  • [ 129644-57-1 ]
  • methyl 2-(5-bromo-2-nitrophenoxy)-5-(trifluoromethoxy)benzoate [ No CAS ]
  • 27
  • [ 129644-57-1 ]
  • 8-bromo-2-(trifluoromethoxy)dibenzo[b,f][1,4]oxazepin-11(10H)-one [ No CAS ]
 

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