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[ CAS No. 106854-77-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 106854-77-7
Chemical Structure| 106854-77-7
Chemical Structure| 106854-77-7
Structure of 106854-77-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 106854-77-7 ]

CAS No. :106854-77-7 MDL No. :MFCD07780193
Formula : C8H6BrF3O Boiling Point : -
Linear Structure Formula :- InChI Key :SMDIDUHBHCDCRQ-UHFFFAOYSA-N
M.W : 255.03 Pubchem ID :22913883
Synonyms :

Calculated chemistry of [ 106854-77-7 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.63
TPSA : 9.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.37
Log Po/w (XLOGP3) : 3.7
Log Po/w (WLOGP) : 4.65
Log Po/w (MLOGP) : 3.32
Log Po/w (SILICOS-IT) : 3.39
Consensus Log Po/w : 3.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.9
Solubility : 0.0324 mg/ml ; 0.000127 mol/l
Class : Soluble
Log S (Ali) : -3.58
Solubility : 0.0664 mg/ml ; 0.00026 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.29
Solubility : 0.0132 mg/ml ; 0.0000519 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.28

Safety of [ 106854-77-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 106854-77-7 ]

* 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 [ 106854-77-7 ]
  • Downstream synthetic route of [ 106854-77-7 ]

[ 106854-77-7 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 106-41-2 ]
  • [ 6226-25-1 ]
  • [ 106854-77-7 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In acetone at 20℃; 1- (methylsulfonyl)-4- [4- (2, 2, 2-trifluoroethoxy) phenyl] piperazine Potassium carbonate (22.89 g, 166 mmol) and 2,2, 2-trifluoroethyl trifluoromethanesulfonate (16.0 g, 69 mmol) were added to a solution of 4-bromophenol (9.57 g, 55 mmol) in acetone (200 mL). The reaction was stirred at room temperature overnight then filtered and concentrated at 300 mbar, 30 C to remove the acetone. This yielded 1-BROMO-4- (2, 2,2- trifluoroethoxy) benzene as a waxy solid (>100percent yield as some acetone still present).
88% With potassium carbonate In acetone at 20℃; To a solution of 411 4-bromophenol (10 g, 58 mmol) in 125 acetone (230 mL) were added 106potassium carbonate (24 g, 0.17 mol) and 412 2,2,2-trifluoroethyl trifluoromethanesulfonate (17 g, 72mmol), and the mixture was stirred at room temperature overnight. The insoluble material was filtered off,acetone was evaporated from the filtrate under reduced pressure (300 mbar, 30° C.). To the obtained residuewas added 12 dichloromethane (200 mL) and the mixture was filtered. The filtrate was concentrated underreduced pressure to give the 413 title compound ( 13 g , 51 mmol, 88percent). 1H NMR (400 MHz, CDCl3) δ 7.44-7.40 (m, 2H), 6.85-6.81 (m, 2H), 4.35-4.29 (m, 2H) .
Reference: [1] Patent: WO2005/822, 2005, A1, . Location in patent: Page/Page column 44
[2] Patent: US2016/332999, 2016, A1, . Location in patent: Paragraph 0576; 0577
  • 2
  • [ 106-41-2 ]
  • [ 433-06-7 ]
  • [ 106854-77-7 ]
YieldReaction ConditionsOperation in experiment
53.3% With potassium carbonate In N,N-dimethyl-formamide at 20 - 120℃; for 6 h; Inert atmosphere 1 -Bromo-4-( 2,2,2-trifluoroethoxy )benzeneTo a stirred solution of trifluoroethyl tosylate (1.5 g, 5.8 mmol) in DMF (20 mL) was added K2CO3 (4 g, 29.4 mmol) followed by addition of p-bromo phenol (1.1 g, 6.46 mmol) at RT under inert atmosphere. The reaction mixture was stirred at 120 °C for 6 h. The volatiles were evaporated under reduced pressure; the residue was diluted with water (5 mL) and extracted with ethyl acetate (3 x 30 mL). The organic layer was washed with water, brine and dried over anhydrous Na2S04, filtered and concentrated in vacuo. The crude compound was purified by silica gel column chromatography eluting with 5percent EtOAc/hexane to afford the desired product (0.8 g, 3.13 mmol, 53.3percent) as semi solid. 1H NMR (200 MHz, CDC13): δ 7.44 - 7.38 (m, 2 H), 6.86-6.80 (m, 2 H), 4.38- 4.25 (m, 2 H).
53.3% With potassium carbonate In N,N-dimethyl-formamide at 20 - 120℃; for 6 h; Inert atmosphere To a stirred solution of trifluoroetfiyl tosylate (1.5 g, 5.8 mmol) in DMF (20 mL) was added K2CO3 (4 g, 29.4 mmol) followed by /?-bromo phenol (1.1 g, 6.46 mmol) at RT under an inert atmosphere. The reaction mixture was stirred at 120 °C for 6 h. The volatiles were evaporated under reduced pressure; the residue was diluted with water (5 mL) and extracted with EtO Ac (3 x 30 mL). The organic layer was washed with water and brine, was dried over anhydrous Na2S04, was filtered and was concentrated in vacuo. The crude compound was purified by silica gel column chromatography eluting with 5percent EtO Ac/hex ane to afford the desired product (0.8 g, 3.13 mmol, 53.3percent) as semi solid. 1H NMR (200 MHz, CDC13): δ 7.44-7.38 (m, 2H), 6.86-6.80 (m, 2H), 4.38- 4.25 (m, 2H).
53.3% at 20 - 120℃; for 6 h; Inert atmosphere To a stirred solution of trifluoroethyl tosylate (1.5 g, 5.8 mmol) in DMF (20 mL) was added K2C03 (4 g, 29.4 mmol) followed by /?-bromo phenol (1.1 g, 6.46 mmol) at RT under an inert atmosphere. The reaction mixture was stirred at 120 °C for 6 h. The volatiles were evaporated under reduced pressure; the residue was diluted with water (5 mL) and extracted with EtOAc (3 x 30 mL). The organic layer was washed with water and brine, was dried over anhydrous Na2S04, was filtered and was concentrated in vacuo. The crude compound was purified by silica gel column chromatography eluting with 5percent EtO Ac/hex ane to afford the desired product (0.8 g, 3.13 mmol, 53.3percent) as semi solid. 1H NMR (200 MHz, CDC13): δ 7.44-7.38 (m, 2H), 6.86-6.80 (m, 2H), 4.38- 4.25 (m, 2H)
Reference: [1] Patent: WO2011/133875, 2011, A2, . Location in patent: Page/Page column 43
[2] Patent: WO2013/110002, 2013, A1, . Location in patent: Page/Page column 43
[3] Patent: WO2013/109998, 2013, A1, . Location in patent: Page/Page column 41
[4] Patent: US2012/329802, 2012, A1, . Location in patent: Page/Page column 26
  • 3
  • [ 75-89-8 ]
  • [ 5467-74-3 ]
  • [ 106854-77-7 ]
YieldReaction ConditionsOperation in experiment
72% With pyridine; copper diacetate; sodium carbonate In 1,2-dichloro-ethane at 20℃; for 14 h; Schlenk technique; Molecular sieve; Sealed tube General procedure: In a nitrogen-filled glove box, a 25 mL Schlenk tube equipped with a magnetic stir bar was charged with Cu(OAc)2 (9.3 mg,0.05 mmol, 0.1 equiv), aryl boronic acid 1 (0.5 mmol, 1.0 equiv),Na2CO3 (106.0 mg, 1.0 mmol, 2.0 equiv) and 4 Å MS (250.0 mg). The vessel was sealed with a septum before removing from the glovebox. The tube was evacuated and backfilled with air for 3 times.Then DCE (5.0 mL), pyridine (39.6 mg, 0.5 mmol, 1.0 equiv) and CF3CH2OH (100.0 mg, 1.0 mmol, 2.0 equiv) were added respectivelyvia syringe. The mixture was stirred vigorously under a balloon ofair at room temperature for 14 h. Then the reaction solution was vacuum-filtered over a sintered-glass funnel with a tightly packedpad of Celite (1 cm thick), and the filter cake was rinsed with DCM(20 mL). The combined filtrates were concentrated. The residue was purified with silica gel column chromatography to provide the desired product.
Reference: [1] Journal of Fluorine Chemistry, 2017, vol. 196, p. 24 - 31
  • 4
  • [ 75-89-8 ]
  • [ 139139-81-4 ]
  • [ 106854-77-7 ]
YieldReaction ConditionsOperation in experiment
83% With sodium hydride In 1,2-dichloro-ethane at 50℃; for 3 h; Trifluoroethanol (1 mmol), bis (4-bromobenzene) iodonium triflate (2 mmol), NaH (1.2 nnol) and 2 mL of dichloroethane were added to a 15 mL tube and stirred at 50 ° C. The reaction After 3 h, silica gel column chromatography gave a yield of 2b of 83percent.
Reference: [1] Patent: CN107200681, 2017, A, . Location in patent: Paragraph 0019; 0020
  • 5
  • [ 25236-64-0 ]
  • [ 95-56-7 ]
  • [ 106854-77-7 ]
YieldReaction ConditionsOperation in experiment
30%
Stage #1: With sodium hydroxide In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃;
Stage #2: at 140℃; for 5 h; Microwave radiation
A solution of bromophenol (3 g) in hexamethylphosphoramide (17.3 ml) is added dropwise to sodium hydroxide (1 equivalent) washed beforehand with ether. The medium is stirred at ambient temperature until gas evolution has ceased. After addition of 2,2,2-trifluoroethyl methanesulphonate (1.2 equivalents), the solution is irradiated under microwave radiation at 140° C. at atmospheric pressure for 5 hours. The reaction medium is subsequently diluted with 150 ml of diethyl ether and washed with water. The organic phase is dried over sodium sulphate, filtered and then concentrated under reduced pressure. Chromatography of the residue on silica gel (cyclohexane 100percent) makes it possible to isolate 1.28 g of the expected product. Yield: 30percent 1H NMR (CDCl3) δ (ppm): 7.40 (d, 2H), 6.81 (d, 2H), 4.32 (m, 2H)
Reference: [1] Patent: US2004/72871, 2004, A1, . Location in patent: Page/Page column 23
  • 6
  • [ 62149-35-3 ]
  • [ 106854-77-7 ]
Reference: [1] Gazzetta Chimica Italiana, 1996, vol. 126, # 7, p. 429 - 434
[2] Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 204, p. 77 - 89
  • 7
  • [ 57946-61-9 ]
  • [ 106854-77-7 ]
Reference: [1] Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 204, p. 77 - 89
[2] Gazzetta Chimica Italiana, 1996, vol. 126, # 7, p. 429 - 434
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