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[ CAS No. 139301-27-2 ] {[proInfo.proName]}

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Chemical Structure| 139301-27-2
Chemical Structure| 139301-27-2
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Product Details of [ 139301-27-2 ]

CAS No. :139301-27-2 MDL No. :MFCD01074648
Formula : C7H6BF3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :HUOFUOCSQCYFPW-UHFFFAOYSA-N
M.W :205.93 Pubchem ID :2734386
Synonyms :

Calculated chemistry of [ 139301-27-2 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 3
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 42.95
TPSA : 49.69 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.01
Log Po/w (WLOGP) : 1.53
Log Po/w (MLOGP) : 0.49
Log Po/w (SILICOS-IT) : -0.13
Consensus Log Po/w : 0.78

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.5
Solubility : 0.648 mg/ml ; 0.00315 mol/l
Class : Soluble
Log S (Ali) : -2.68
Solubility : 0.43 mg/ml ; 0.00209 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.92
Solubility : 2.47 mg/ml ; 0.012 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.9

Safety of [ 139301-27-2 ]

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

Application In Synthesis of [ 139301-27-2 ]

* 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 [ 139301-27-2 ]
  • Downstream synthetic route of [ 139301-27-2 ]

[ 139301-27-2 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 139301-27-2 ]
  • [ 828-27-3 ]
YieldReaction ConditionsOperation in experiment
92% With iron(III) oxide; oxygen In tetrahydrofuranIrradiation General procedure: In atypical procedure, a flask containing phenylboronic acid (100 mg, 0.82 mmol) was taken and to it were added 10 mol percent of iron(III) oxide photocatalyst(13.1 mg) and tetrahydrofuran (2 ml). The reaction mixture was kept for stirring under diffused sunlight in ordinary open flask until the starting material is consumed on TLC. Quenched with water after completion and the catalyst was filtered off, the filtrate was concentrated in vacuo. The crudeproduct was purified on silica (100–200 mesh) column chromatography (15percentethylacetate/hexane) to offer 73.2 mg (in 95percent yield) of pure crystalline phenol.
92% With iron(III) oxide; oxygen In tetrahydrofuran at 20℃; Irradiation General procedure: In a typical procedure, a flask containing phenylboronic acid (100 mg, 0.82 mmol) was taken and to it were added 10 mol percent of iron(III) oxide photocatalyst(13.1 mg) and tetrahydrofuran (2 ml). The reaction mixture was kept for stirring under diffused sunlight in ordinary open flask until the starting material is consumed on TLC. Quenched with water after completion and the catalyst was filtered off, the filtrate was concentrated in vacuo. The crude product was purified on silica (100–200 mesh) column chromatography (15percentethylacetate/hexane) to offer 73.2 mg (in 95percent yield) of pure crystalline phenol.
72% With p-benzoquinone; potassium hydroxide In water for 23 h; Reflux; Green chemistry General procedure: A mixture of 1,4-benzoquinone (32.4 mg, 0.3 mmol), boronic acid 1 (1 mmol), and KOH (168 mg, 3.0 mmol) in H2O (5 mL) was stirred at reflux temperature under air for 15−45 h. After the full consumption of 1 (monitored by TLC, eluent: PE–EtOAc, 10:1), the reaction was quenched carefully with aq 2 M HCl (15 mL). The resulting mixture was extracted with EtOAc (3 × 20 mL). The combined organic layers were washed with H2O (30 mL) and brine (10 mL), and dried (Na2SO4). After the removal of the solvent, the resulting residue was purified by chromatography (silica gel, 20 percent EtOAc in PE) to give the respective products 2.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 4, p. 811 - 814
[2] Tetrahedron Letters, 2015, vol. 55, # 4, p. 811 - 814
[3] Synthesis (Germany), 2014, vol. 46, # 3, p. 295 - 300
  • 2
  • [ 55305-43-6 ]
  • [ 139301-27-2 ]
  • [ 332-25-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 2, p. 519 - 522
  • 3
  • [ 75-05-8 ]
  • [ 139301-27-2 ]
  • [ 332-25-2 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 38, p. 13246 - 13252
  • 4
  • [ 20154-03-4 ]
  • [ 139301-27-2 ]
YieldReaction ConditionsOperation in experiment
52% With sodium hydride In N,N-dimethyl-formamide at 80 - 100℃; for 14 h; Step (ii): Synthesis of 2-(4-Trifluoromethoxy-phenyl)-4-(3-trifluoromethyl-pyrazol-l- yl)-quinoline (E 18); Compound 24 (200 mg, 0.62 mmol) was added to a stirred solution of compound 21 (210 mg, 1.55 mmol) and NaH (1.55 mmol) in dry DMF (5.0 mL), EPO <DP n="140"/>under nitrogen. The mixture was stirred at 80-100 0C for about 14 hrs. After this time, the reaction the mixture was cooled to room temperature, diluted with ethyl acetate, and washed with 2N HCl. The organic layer was collected, washed with water followed by saturated NaCl solution, dried over anhydrous sodium sulfate, and evaporated to dryness. The residue was purified by column chromatography to give the desired product (yield 55 percent). Melting range: 108-110 0C1H NMR (400 MHz, CDCl3) δ 8.28-8.23 (m, 3H), 8.02-8.00 (m, 2H), 7.95 (s, IH), 7.86-7.81 (m, IH), 7.65-7.61 (m, IH), 7.39-7.37 (m, 2H), 6.89 (d, J=2.7Hz, IH). IR (Cm"1): 1607, 1505, 1480 MS (m/z): 424 (M+, 100percent)
Reference: [1] Patent: WO2006/58201, 2006, A2, . Location in patent: Page/Page column 138-139
  • 5
  • [ 407-14-7 ]
  • [ 139301-27-2 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 4, p. 691 - 695
  • 6
  • [ 5419-55-6 ]
  • [ 407-14-7 ]
  • [ 139301-27-2 ]
YieldReaction ConditionsOperation in experiment
90.4% With hydrogenchloride; n-butyllithium; sodium chloride In tetrahydrofuran; n-heptane EXAMPLE 1E
4-(trifluoromethoxy)phenylboronic Acid
A solution of 1-bromo-4-(trifluoromethoxy)benzene (1.69 kg) and triisopropyl borate (1.46 kg) in THF (6.75 L) at -70° C. was treated with 2.25 M butyllithium in hexanes (3.27 L) over 2.3 hours, stirred for 10 minutes, treated with 6M HCl (1.52 L) over 50 minutes, stirred for 18 hours at room temperature, and poured into a mixture of heptane (8.43 L) and 20percent (w/w) sodium chloride (8.44 kg).
This mixture was stirred for 10 minutes and separated into an aqueous fraction and an organic fraction.
The organic fraction was concentrated to provide a white paste.
The paste was dried under vacuum (100 mmHg) at ambient temperature with a nitrogen bleed for 2 days then at 40-50° C. for 18 hours to provide 1.306 kg (90.4percent) of the desired product as a solid. 1H NMR (CDCl3, 300 MHz) δ 7.24-7.19 (m, 2H), 8.14-8.10 (m, 2H) with additional absorptions at 7.19-7.15 (m, 2H) and 8.04-8.00 (m, 2H) corresponding to the cyclic boronic acid trimer.
Reference: [1] Patent: US2002/19539, 2002, A1,
[2] Patent: US2002/19539, 2002, A1,
  • 7
  • [ 13675-18-8 ]
  • [ 407-14-7 ]
  • [ 139301-27-2 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
  • 8
  • [ 139301-27-2 ]
  • [ 956697-53-3 ]
YieldReaction ConditionsOperation in experiment
61.1% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 130℃; Sealed tube 4- (trifluoromethoxy) phenylboronic acid (254mg, 1.24mmol), 3-bromo -N- [6- (2,6- dimethyl - morpholin-4-yl) - pyridine 3-yl] -4-methyl -benzamide 5 (250mg, 0.62mmol), Pd (PPh 3) 4 (36mg, 0.03mmol), Na 2 CO 3 (2.0Maqueous solution, 1.23mL, 2.4mmol) and a mixture of DME (4.5mL) in a sealed tube and heated at130 ° C overnight. The reaction mixture was diluted with EtOAc and water. Theaqueous layer was extracted with EtOAc. The combined organic layers were washedwith brine and concentrated to give a crude product, which was then purified bypreparative mass triggered HPLC (C 18 column and eluted with 0.05percent TFA in CH 3CN-H 2 O elution) to give N - (6 - ((2S, 6R) -2,6- dimethyl-morpholino)pyridin-3-yl) -2-methyl-4 '- (trifluoromethoxy) biphenyl-3-carboxylic amide(183.5mg, yield 61.1percent).
Reference: [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 47, p. 9562 - 9571
[2] Patent: CN103893184, 2016, B, . Location in patent: Paragraph 0096; 0100
[3] Drugs of the Future, 2014, vol. 39, # 10, p. 677 - 684
  • 9
  • [ 139301-27-2 ]
  • [ 956697-53-3 ]
Reference: [1] Drugs of the Future, 2014, vol. 39, # 10, p. 677 - 684
  • 10
  • [ 105-36-2 ]
  • [ 139301-27-2 ]
  • [ 1206550-93-7 ]
Reference: [1] Tetrahedron, 2010, vol. 66, # 42, p. 8238 - 8241
  • 11
  • [ 1166819-53-9 ]
  • [ 139301-27-2 ]
  • [ 1262618-39-2 ]
Reference: [1] Patent: US2011/21521, 2011, A1, . Location in patent: Page/Page column 33
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