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[ CAS No. 35853-41-9 ] {[proInfo.proName]}

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Chemical Structure| 35853-41-9
Chemical Structure| 35853-41-9
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Product Details of [ 35853-41-9 ]

CAS No. :35853-41-9 MDL No. :MFCD00075091
Formula : C11H5F6NO Boiling Point : -
Linear Structure Formula :- InChI Key :JIWHKBAFGFPZKM-UHFFFAOYSA-N
M.W : 281.15 Pubchem ID :736140
Synonyms :

Calculated chemistry of [ 35853-41-9 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.18
Num. rotatable bonds : 2
Num. H-bond acceptors : 7.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.57
TPSA : 32.86 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.06
Log Po/w (XLOGP3) : 3.34
Log Po/w (WLOGP) : 5.87
Log Po/w (MLOGP) : 2.78
Log Po/w (SILICOS-IT) : 4.6
Consensus Log Po/w : 3.73

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.94
Solubility : 0.0319 mg/ml ; 0.000114 mol/l
Class : Soluble
Log S (Ali) : -3.71
Solubility : 0.0552 mg/ml ; 0.000196 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.38
Solubility : 0.00118 mg/ml ; 0.00000419 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.92

Safety of [ 35853-41-9 ]

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

Application In Synthesis of [ 35853-41-9 ]

* 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 [ 35853-41-9 ]
  • Downstream synthetic route of [ 35853-41-9 ]

[ 35853-41-9 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 35853-41-9 ]
  • [ 35853-45-3 ]
YieldReaction ConditionsOperation in experiment
96% at 150℃; for 6 h; Inert atmosphere Phosphorous oxybromide (4 g, 14.2 mmol), under an argon atmosphere, was heated to 90 °C until complete dissolution of the solid. Compound 5 (4.08 g, 14.2 mmol) was added to this hot solution and the bath temperature was increased to 150 °C. After 6 h, the resulting mixture was allowed to cool to room temperature. The reaction mixture was quenched by addition of ice-cold water and the precipitate formed was filtered and washed with water to afford the expected compound 6a (4.70 g, 96percent) as a white solid. Rf 0.79 (cyclohexane/Et2O 5:1); mp: 60 °C; 1H NMR (300 MHz, CDCl3) δ 7.82 (t, J = 7.9 Hz, 1H), 8.11 (s, 1H), 8.22 (d, J = 7.3 Hz, 1H), 8.46 (d, J = 8.6 Hz, 1H), NMR data were in agreement with the lit.;13 13C NMR (125 MHz, CDCl3) δ 120.9 (q, J = 276.0 Hz), 122.0 (q, J = 2.0 Hz), 123.6 (q, J = 273.8 Hz), 128.9, 129.4, 129.8 (q, J = 30.8 Hz), 130.5 (q, J = 5.3 Hz), 131.5, 138.5, 144.5, 148.6 (q, J = 36.1 Hz); IR νmax = 1577, 1422, 1302, 1136, 1098, 1010, 876, 824 cm-1; GCMS (m/z): 343; HRMS calcd for C11H4BrF6NNa (M+Na)+ 365.9329, found 365.9346.
96% at 90 - 150℃; for 6 h; Inert atmosphere 4-bromo-2,8-bis(trifluoromethyl)quinoline (6a)Phosphorous oxybromide (4 g, 14.2 mmol), under argon atmosphere, was heated to 90 °C until complete dissolution of the solid. 4-hydroxyquinoline 5 (4.08 g, 14.2 mmol) was added to this hot solution and the bath temperature was increased to 150 °C. After 6 h, the resulting mixture was cooled to room temperature. The reaction mixture was quenched by addition of ice-cold water and the precipitated formed was filtered and washed with water to afford the expected compound 6a (4.70 g, 96percent) as a white solid. Rf 0.79 (cyclohexane/Et20 5:1); mp: 60 °C; 1H NMR (300 MHz, CDCI3) δ 7.82 (t, J = 7.9 Hz, 1 H), 8. (s, 1 H), 8.22 (d, J = 7.3 Hz, 1 H), 8.46 (d, J = 8.6 Hz, 1 H), NMR data were in agreement with the lit.:[13]; 13C NMR (125 MHz, CDCI3) δ 120.9 (q, J = 276.0 Hz), 122.0 (q, J = 2.0 Hz), 123.6 (q, J = 273.8 Hz), 128.9, 129.4, 129.8 (q, J = 30.8 Hz), 130.5 (q, J = 5.3 Hz), 131.5, 138.5, 144.5, 148.6 (q, J = 36.1 Hz); IR umax=1577, 1422, 1302, 1 136, 1098, 1010, 876, 824 cm"1; GCMS (m/z): 343; HRMS calcd for C11H4BrF6NNa (M+Na)+ 365.9329,
96% at 150℃; for 6 h; Inert atmosphere 4-bromo-2,8-bis(trifluoromethyl)quinoline (6a)
Phosphorous oxybromide (4 g, 14.2 mmol), under argon atmosphere, was heated to 90 °C until complete dissolution of the solid. 5 (4.08 g, 14.2 mmol) was added to this hot solution and the bath temperature was increased to 150 °C.
After 6 h, the resulting mixture was allowed to cool to room temperature.
The reaction mixture was quenched by addition of ice-cold water and the precipitated formed was filtered and washed with water to afford the expected compound 6a (4.70 g, 96percent) as a white solid. Rf0.79 (cyclohexane/Et2O 5:1); mp:
60 °C; 1H NMR (300 MHz, CDCl3) δ 7.82 (t, J = 7.9 Hz, 1H), 8.11 (s, 1H), 8.22 (d, J = 7.3 Hz, 1H), 8.46 (d, J = 8.6 Hz, 1H), NMR data were in agreement with the lit.:[13]; 13C NMR (125 MHz, CDCl3) δ 120.9 (q, J = 276.0 Hz), 122.0 (q, J = 2.0 Hz), 123.6 (q, J = 273.8 Hz), 128.9, 129.4, 129.8 (q, J = 30.8 Hz), 130.5 (q, J = 5.3 Hz), 131.5, 138.5, 144.5, 148.6 (q, J = 36.1 Hz); IR Umax=1577, 1422, 1302, 1136, 1098, 1010, 876, 824 cm-1; GCMS (m/z): 343; HRMS calcd for C11H4BrF6NNa (M+Na)+365.9329, found 365.9346.
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 47, p. 14070 - 14074[2] Angew. Chem., 2015, vol. 127, # 47, p. 14276 - 14280,5
[3] Journal of Organic Chemistry, 2016, vol. 81, # 20, p. 9567 - 9575
[4] Tetrahedron Asymmetry, 2011, vol. 22, # 2, p. 138 - 148
[5] Patent: WO2012/107532, 2012, A1, . Location in patent: Page/Page column 20-21
[6] Patent: EP2487157, 2012, A1, . Location in patent: Page/Page column 12
[7] Monatshefte fur Chemie, 2008, vol. 139, # 2, p. 179 - 181
[8] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1347 - 1351
[9] Journal of Medicinal Chemistry, 2011, vol. 54, # 18, p. 6277 - 6285
  • 2
  • [ 372-31-6 ]
  • [ 88-17-5 ]
  • [ 35853-41-9 ]
YieldReaction ConditionsOperation in experiment
23% at 120℃; for 3 h; Inert atmosphere 2-(Trifluoromethyl)aniline (0.54 mL, 4.3 mmol) and ethyl 4,4,4-trifluoro-3-oxobutanoate (0.62 mL, 4.3 mmol) was added to a round bottomed flask equipped with a large oval stirrer bar followed by polyphosphoric acid (4.0 g). The reaction mass was stirred at 120 °C for 3 h under N2. The gold brown sticky mass was then quenched with ice water (50 mL) and extracted with DCM (2 × 20 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to offer the product as beige solid that did not require purification (0.27 g, 23 percent yield).
Reference: [1] European Journal of Medicinal Chemistry, 2010, vol. 45, # 8, p. 3374 - 3383
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2012, vol. 51, # 9, p. 1411 - 1416,6
[3] Monatshefte fur Chemie, 2008, vol. 139, # 2, p. 179 - 181
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 23, p. 5466 - 5469
[5] CrystEngComm, 2018, vol. 20, # 16, p. 2316 - 2323
  • 3
  • [ 35853-41-9 ]
  • [ 83012-13-9 ]
YieldReaction ConditionsOperation in experiment
50% at 80℃; for 5 h; Inert atmosphere; Reflux 2,8-Bis(trifluoromethyl)quinoline-4-ol (0.25 g, 0.89 mmol) was dissolved in POCl3 (5 mL) and refluxed at 80 °C for 5 h under N2. The reaction was quenched with 30 mL ice water and extracted with DCM (2 ×20 mL). The organic layers were pooled, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to offer the product as pale yellow solid that was used as is for the next reaction (0.13 g,50 percent yield).
Reference: [1] Tetrahedron, 1991, vol. 47, # 36, p. 7609 - 7614
[2] European Journal of Medicinal Chemistry, 2010, vol. 45, # 8, p. 3374 - 3383
[3] Monatshefte fur Chemie, 2008, vol. 139, # 2, p. 179 - 181
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 23, p. 5466 - 5469
[5] Patent: US4429130, 1984, A,
[6] CrystEngComm, 2018, vol. 20, # 16, p. 2316 - 2323
  • 4
  • [ 35853-41-9 ]
  • [ 35853-55-5 ]
Reference: [1] Tetrahedron, 1989, vol. 45, # 5, p. 1409 - 1414
[2] Tetrahedron, 1989, vol. 45, # 5, p. 1409 - 1414
[3] Tetrahedron, 1991, vol. 47, # 36, p. 7609 - 7614
[4] Tetrahedron, 1991, vol. 47, # 36, p. 7609 - 7614
  • 5
  • [ 35853-41-9 ]
  • [ 51773-92-3 ]
Reference: [1] Tetrahedron, 1989, vol. 45, # 5, p. 1409 - 1414
[2] Tetrahedron, 1989, vol. 45, # 5, p. 1409 - 1414
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