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[ CAS No. 142738-94-1 ] {[proInfo.proName]}

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Chemical Structure| 142738-94-1
Chemical Structure| 142738-94-1
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Product Details of [ 142738-94-1 ]

CAS No. :142738-94-1 MDL No. :MFCD01631504
Formula : C8H7F3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :OKSRAPDSZKICKZ-UHFFFAOYSA-N
M.W : 192.14 Pubchem ID :2777188
Synonyms :

Calculated chemistry of [ 142738-94-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.62
TPSA : 18.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.38
Log Po/w (XLOGP3) : 3.42
Log Po/w (WLOGP) : 3.85
Log Po/w (MLOGP) : 1.95
Log Po/w (SILICOS-IT) : 2.38
Consensus Log Po/w : 2.8

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.33
Solubility : 0.09 mg/ml ; 0.000468 mol/l
Class : Soluble
Log S (Ali) : -3.49
Solubility : 0.0625 mg/ml ; 0.000325 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.15
Solubility : 0.134 mg/ml ; 0.0007 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.65

Safety of [ 142738-94-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 142738-94-1 ]

* 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 [ 142738-94-1 ]

[ 142738-94-1 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 142738-94-1 ]
  • [ 142739-14-8 ]
  • [ 142739-13-7 ]
YieldReaction ConditionsOperation in experiment
With sulfur trioxide In nitromethane-d3 at 22℃; for 0.166667h; Yield given. Yields of byproduct given;
  • 2
  • [ 124-38-9 ]
  • [ 142738-94-1 ]
  • 2-methoxy-6-(trifluoromethoxy)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: 1-methoxy-3-(trifluoromethoxy)benzene With sec.-butyllithium In tetrahydrofuran; hexane at -100℃; for 2h; Stage #2: carbon dioxide In tetrahydrofuran; hexane Further stages.;
  • 3
  • [ 827-99-6 ]
  • [ 74-88-4 ]
  • [ 142738-94-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In water; ethyl acetate; N,N-dimethyl-formamide; at 0 - 20℃; for 13.5h; To a suspension of 20.0 g of <strong>[827-99-6]3-(trifluoromethoxy)phenol</strong> and 23.3 g of K2CO3 (anhydrous) in DMF (100 ml) was added 23.9 g of iodine methane under ice cooling, then the reaction mixture was warmed to room temperature, and was stirred at room temperature for 13 hours. To the reaction solution was added EtOAc (100 ml) and purified water (150 ml), and the resulting mixture was stirred for 30 minutes. After liquid separation, the aqueous layer was extracted with EtOAc (50 ml×2), the combined organic layer was washed with purified water (100 ml×3) and with saturated brine (50 ml) and dried overover MgSO4, then, the drying agent was separated by filtration, and the solvent was removed under reduced pressure to obtain 27.7 g of the title compound (crude form, yellow oil). The present compound was used in the next reaction without purification.MS (CI pos.) m/z: 193 ([M+H]+)1H-NMR (300 MHz, CDCl3) delta (ppm); 3.81 (s, 3H), 6.73-6.87 (m, 3H), 7.25-7.32 (m, 1H)
  • 4
  • [ 142738-94-1 ]
  • [ 905077-14-7 ]
  • [ 905077-18-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methoxy-3-(trifluoromethoxy)benzene With sulfuric acid In nitromethane; chloroform; water at 0 - 20℃; for 72.55h; Stage #2: With potassium hydroxide In water 1.G1.2 Under a nitrogen atmosphere, to a solution of 27.0 g of compound obtained in Step G1-1 in nitromethane (270 ml) was added dropwise a solution of 9.86 g of anhydrous sulfuric acid in nitromethane (100 ml) over 3 minutes under ice cooling. After warming to room temperature, the reaction mixture was stirred for 3 days at room temperature. To the reaction solution was added water (100 ml) and CHCl3 (50 ml), and the resulting mixture was stirred at room temperature for 30 minutes. After liquid separation, and the aqueous layer was washed with CHCl3 (50 ml). The obtained aqueous layer was cooled with ice, neutralized with a 2 mol/L KOH aqueous solution (PH=9). The neutralized solution was dried under reduced pressure to obtain 32.9 g of the title compound (crude form, brown solid). The present compound was used in the next reaction without purification.MS (ESI pos.) m/z: 333 ([M+Na]+)1H-NMR (300 MHz, DMSO-d6) δ (ppm); 3.78 & 3.79 (each-s, 3H), 6.72-6.95 (m, 3H), 7.75 (t, J=8.9 Hz, 1H)
  • 5
  • [ 142738-94-1 ]
  • C12H14F3NO3 [ No CAS ]
  • C12H14F3NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / 3 h / 20 °C 2: tetrakis(acetonitrile)copper(I)tetrafluoroborate; N-ethyl-N,N-diisopropylamine / acetonitrile; dimethyl sulfoxide / 12 h / 40 °C
  • 6
  • [ 1493-13-6 ]
  • [ 142738-94-1 ]
  • C22H31IO4S [ No CAS ]
  • C24H29F6IO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile at 20℃; for 3h;
  • 7
  • [ 217813-03-1 ]
  • [ 142738-94-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-bromo-1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane; perhydrodibenzo-18-crown-6; potassium fluoride / ethyl acetate / 12 h / 20 °C / Glovebox 2: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
  • 8
  • 2-bromo-1-methoxy-3-(trifluoromethoxy)benzene [ No CAS ]
  • [ 142738-94-1 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
  • 9
  • [ 1006904-72-8 ]
  • 3-methoxybenzenediazonium tetrafluoroborate [ No CAS ]
  • [ 142738-94-1 ]
YieldReaction ConditionsOperation in experiment
51% In acetonitrile at -40℃; for 2h; Inert atmosphere; 2 Synthesis, separation and purification of 1-methoxy-3-trifluoromethoxybenzene:3-methoxyphenyldiazonium tetrafluoroborate (1 mmol, 1.0 eq) was added to a 50 mL round bottom flask under N2.Seal with a rubber stopper and then use a syringe to the round bottom flask4 ml of anhydrous acetonitrile after degassing was added, and the reaction flask was stirred under a dry ice bath at -40 °C.Then 0.5 M of AgOCF3 acetonitrile solution (6 ml, 3 mmol, 3.0 eq) was added to the reaction flask with a syringe.The reaction was continued at -40 ° C for 2 hours, and then naturally warmed to room temperature for 13 hours.After the reaction was completed, the reaction solution was extracted twice with 20 ml of dichloromethane.The resulting organic phase is then dried over anhydrous sodium sulfate.Filtration and rotary distillation under reduced pressure gave a crude product with a small solvent.The crude product is then separated on a silica gel column using a mixture of low boiling petroleum ether: dichloromethane = 10:1.The final product was obtained: 1-methoxy-3-trifluoromethoxybenzene as a pale yellow oily liquid, yield 51%.
  • 10
  • [ 1006904-72-8 ]
  • [ 536-90-3 ]
  • [ 142738-94-1 ]
YieldReaction ConditionsOperation in experiment
96 mg Stage #1: m-Anisidine With tetrafluoroboric acid; tert.-butylnitrite In ethanol at 0 - 20℃; for 1h; Schlenk technique; Stage #2: silver(I) trifluoromethoxide In acetonitrile at -40 - 20℃;
  • 11
  • [ 512-56-1 ]
  • [ 827-99-6 ]
  • [ 142738-94-1 ]
YieldReaction ConditionsOperation in experiment
88% With calcium hydroxide; In neat (no solvent); at 80℃; for 2.5h;Sealed tube; General procedure: A 10-mL glass reaction tube fitted with a resealable Teflon valve wascharged with the heteroatom nucleophile substrate (1.0 mmol, 1.0equiv), Ca(OH)2 (100 mg, 1.35 mmol, 1.35 equiv), and TMP (0.20 mL,1.7 mmol, 1.7 equiv). The flask was sealed and heated at 80 C withoutstirring until TLC indicated complete conversion. The reactionwas then worked up as described below. Workup Procedure AAfter complete conversion, 1 N HCl (5 mL) was added and the mixturewas extracted with CH2Cl2 (10 mL). The organic phase was separated,washed with H2O (20 mL), dried over Na2SO4, filtered, and then concentratedin vacuo. The resulting residue was purified by silica gelcolumn chromatography to afford the desired methylated product.Workup Procedure BAfter complete conversion, petroleum ether (5 mL) was added, andthe solid was smashed into fine particles using a spatula and sonicatedfor 5 min. The resulting residue was then directly subjected to silicagel column chromatography to afford the desired methylated product.Workup Procedure CAfter complete conversion, CH2Cl2 (5 mL) was added, and the mixturewas filtered through a pad of Celite, washed with H2O (10 mL), andextracted with EtOAc (5 × 20 mL). The organic phase was separated,dried over Na2SO4, filtered, and concentrated in vacuo. The resultingresidue was purified by silica gel column chromatography to affordthe desired methylated product.
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