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Product Details of [ 63619-51-2 ]

CAS No. :63619-51-2 MDL No. :MFCD00096777
Formula : C17H19BrO Boiling Point : -
Linear Structure Formula :- InChI Key :XSGGLCGBXDPDLL-UHFFFAOYSA-N
M.W : 319.24 Pubchem ID :2801388
Synonyms :

Calculated chemistry of [ 63619-51-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.29
Num. rotatable bonds : 6
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 85.3
TPSA : 9.23 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.91
Log Po/w (XLOGP3) : 6.17
Log Po/w (WLOGP) : 5.69
Log Po/w (MLOGP) : 4.98
Log Po/w (SILICOS-IT) : 5.66
Consensus Log Po/w : 5.28

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.78
Solubility : 0.000533 mg/ml ; 0.00000167 mol/l
Class : Moderately soluble
Log S (Ali) : -6.15
Solubility : 0.000227 mg/ml ; 0.000000712 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -7.49
Solubility : 0.0000103 mg/ml ; 0.0000000322 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.11

Safety of [ 63619-51-2 ]

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 [ 63619-51-2 ]

* 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 [ 63619-51-2 ]
  • Downstream synthetic route of [ 63619-51-2 ]

[ 63619-51-2 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 544-92-3 ]
  • [ 63619-51-2 ]
  • [ 52364-71-3 ]
Reference: [1] Molecular crystals and liquid crystals, 1981, vol. 75, # 1-4, p. 233 - 247
  • 2
  • [ 110-53-2 ]
  • [ 29558-77-8 ]
  • [ 63619-51-2 ]
YieldReaction ConditionsOperation in experiment
95.9% With potassium carbonate In butanone for 8 h; Reflux General procedure: A suspension of 4-bromo-4'-hydroxybiphenyl (13) (3.5 g, 14.11 mmol), 1-bromoheptane (3.75 g, 21.05 mmol) and K2CO3 (4.9 g, 35.28 mmol) in 2-butanone (25 mL) was refluxed for 8 h. After cooling, the reaction mixture was diluted by CH2Cl2 (50 mL). After filtration, the organic layer was washed by H2O (50 mL) and saturated brine (50 mL), dried over anhydrous Na2SO4, and filtrated. The solvent was condensed to 15 mL under reduced pressure, and the residue was collected and washed by cool hexane (0 °C) to afford 14c (4.6 g, yield 94.3percent) as white solid.
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 196 - 208
[2] Chemistry Letters, 2010, vol. 39, # 5, p. 513 - 515
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 4, p. 1474 - 1477
[4] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 339, p. 145 - 158
[5] Patent: US5948753, 1999, A,
[6] Patent: US5514651, 1996, A,
[7] Patent: US5516756, 1996, A,
[8] Patent: US5646245, 1997, A,
[9] Patent: US5741775, 1998, A,
[10] Patent: US5854213, 1998, A,
[11] Patent: US6268338, 2001, B1,
  • 3
  • [ 628-17-1 ]
  • [ 29558-77-8 ]
  • [ 63619-51-2 ]
YieldReaction ConditionsOperation in experiment
96% With sodium hydroxide; tetrabutylammomium bromide In water Alternative Preparation of 4-bromo-4'-pentyloxybiphenyl 1(a):
4-Bromo-4'-hydroxybiphenyl (12.5 g, 50.2 mmol) was added to a solution of NaOH (2.28 g, 97percent pure, 55.2 mmol) in deionized H2O (150 ml), followed by the addition of 1-iodopentane (11.9 g, 60.2 mmol) and tetrabutylammonium bromide (0.82 g, 2.5 mmol).
The mixture was stirred at 90° C. for 3.75 h until the solids went into solution.
Then, as the reaction proceeded, the desired product began to precipitate.
The mixture was slowly cooled and then filtered to provide a solid which was washed with deionized water until the pH of the filtrate was neutral and then dried for 16 h in a vacuum oven at 30° C. Yield: 15.41 g (96percent) of 5a. Rf 0.5 (97:3 hexanes/EtOAc).
1H NMR: δ 0.93 (t, 3H, J=6.9 Hz); 1.41 (m, 4H); 1.79 (m, 2H); 3.97 (t, 2H, J=6.6 Hz); 6.98 (m, 2H); 7.23 (m,6H).
13C NMR: δ 14.03; 22.43; 28.22; 28.98; 68.12; 114.91; 120.71; 127.93; 128.27; 131.77; 132.24; 139.82; 159.03. MS(FAB+): m/z 320. IR(CHCl3): 2960, 2936, 2874, 1608, 1518, 1485, 1475 cm-1 Analysis for C17H19BrO: Calcd: C, 63.96; H. 6.00; Br, 25.0; Found: C, 64.10; H. 5.97; Br, 25.28.
96% With sodium hydroxide; tetrabutylammomium bromide In water Alternative Preparation of 4-bromo-4'-pentyloxybiphenyl 1(a):
4-Bromo-4'-hydroxybiphenyl (12.5 g, 50.2 mmol) was added to a solution of NaOH (2.28 g, 97percent pure, 55.2 mmol) in deionized H2O (150 ml), followed by the addition of 1-iodopentane (11.9 g, 60.2 mmol) and tetrabutylammonium bromide (0.82 g, 2.51 mmol).
The mixture was stirred at 90° C. for 3.75 h until the solids went into solution.
Then, as the reaction proceeded, the desired product began to precipitate.
The mixture was slowly cooled and then filtered to provide a solid which was washed with deionized water until the pH of the filtrate was neutral and then dried for 16 h in a vacuum oven at 30° C. Yield: 15.41 g (96percent) of 5a. Rf 0.5 (97:3 hexanes/EtOAc).
1H NMR: δ0.93 (t, 3H, J=6.9 Hz); 1.41 (m, 4H); 1.79 (m, 2H); 3.97 (t, 2H, J=6.6 Hz); 6.98 (m, 2H); 7.23 (m, 6H).
13C NMR: δ14.03; 22.43; 28.22; 28.98; 68.12; 114.91; 120.71; 127.93; 128.27; 131.77; 132.24; 139.82; 159.03. MS(FAB+): m/z 320. IR(CHC13): 2960, 2936, 2874, 1608, 1518, 1485, 1475 cm-1.
Analysis for C17H19BrO: Calcd: C, 63.96; H. 6.00; Br, 25.0; Found: C, 64.10; H. 5.97; Br, 25.28.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 3, p. 489 - 493
[2] Patent: US2003/54981, 2003, A1,
[3] Patent: US2002/151474, 2002, A1,
[4] Patent: US2002/160942, 2002, A1,
[5] Patent: EP906915, 1999, A1,
  • 4
  • [ 628-17-1 ]
  • [ 29558-77-8 ]
  • [ 78-93-3 ]
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Reference: [1] Patent: US2002/151474, 2002, A1,
[2] Patent: US2002/160942, 2002, A1,
[3] Patent: EP906915, 1999, A1,
  • 5
  • [ 106-37-6 ]
  • [ 693-25-4 ]
  • [ 63619-51-2 ]
Reference: [1] Doklady Chemistry, 1993, vol. 332, # 1-3, p. 195 - 197[2] Dokl. Akad. Nauk SSSR Ser. Khim., 1993, vol. 332, # 1, p. 48 - 49
  • 6
  • [ 106-37-6 ]
  • [ 115171-02-3 ]
  • [ 63619-51-2 ]
Reference: [1] Russian Journal of Organic Chemistry, 1995, vol. 31, # 11, p. 1480 - 1486[2] Zhurnal Organicheskoi Khimii, 1995, vol. 31, # 11, p. 1650 - 1656
  • 7
  • [ 148-86-7 ]
  • [ 63619-51-2 ]
Reference: [1] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 339, p. 145 - 158
  • 8
  • [ 92-69-3 ]
  • [ 63619-51-2 ]
Reference: [1] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 339, p. 145 - 158
  • 9
  • [ 84244-98-4 ]
  • [ 63619-51-2 ]
Reference: [1] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 339, p. 145 - 158
  • 10
  • [ 110-53-2 ]
  • [ 78079-08-0 ]
  • [ 63619-51-2 ]
Reference: [1] Molecular crystals and liquid crystals, 1981, vol. 75, # 1-4, p. 233 - 247
  • 11
  • [ 14047-29-1 ]
  • [ 63619-51-2 ]
  • [ 158938-08-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 3, p. 489 - 493
  • 12
  • [ 63619-51-2 ]
  • [ 158938-08-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 17, p. 3271 - 3281
[2] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 196 - 208
  • 13
  • [ 63619-51-2 ]
  • [ 158937-25-8 ]
YieldReaction ConditionsOperation in experiment
94.4%
Stage #1: With n-butyllithium In tert-butyl methyl ether at -20℃; for 2 h; Inert atmosphere
Stage #2: With Triisopropyl borate In tetrahydrofuran; tert-butyl methyl ether at -60 - 20℃;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; tert-butyl methyl ether at 20℃; for 0.166667 h;
General procedure: n-BuLi (2.5 M, 7.4 mL, 18 mmol) was added dropwise to a solution of compound 14c (4.5 g, 13 mmol) in MTBE (50 mL) at -20 °C under nitrogen atmosphere. After stirring for 2 h, the reaction mixture was cooled to -60 °C and was added THF (6 mL). Then, a solution of (i-PrO)3B (6.1 mL, 26 mmol) in MTBE (8 mL) was added dropwise to the resulting mixture and was stirred for 1 h. The reaction mixture was allowed to warm to room temperature, stirred overnight and treated with 2 M HCl (50 mL) for 10 min. The organic layer was separated and the solvent was evaporated under reduced pressure. The residue was added hexane (40 mL) and stirred for 10 min. After filtration, the filter cake was washed by hexane-MTBE (8: 1) to give 15c (3.7 g, yield 91.4percent) as white solid.
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 196 - 208
[2] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 339, p. 145 - 158
  • 14
  • [ 5419-55-6 ]
  • [ 63619-51-2 ]
  • [ 158937-25-8 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - -65℃; for 2.25 h;
Stage #2: at -78 - 20℃; for 1.16667 h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane
31,9 g (0,1 mol) 4-Brom-4'-n-pentoxy[1,1']biphenyl werden unter Stickstoffatmosphaere in 640 ml Tetrahydrofuran geloest, auf -78°C gekuehlt und innerhalb von 2 Stunden tropfenweise mit 67 ml (0,11 mol) einer 15percentigen Loesung von n-Butyilithium in Hexan versetzt. Dabei wird die Innentemperatur in einem Bereich von -78°C bis -65°C gehalten. Nach beendeter Zugabe wird die dicke, milchige Suspension weitere 15 Minuten bei -78°C geruehrt und im Anschluss daran mit 25,5 ml (0,11 mol) Triisopropylborat innerhalb 15 Minuten bei -78°C tropfenweise versetzt. Nach beendeter Boratzugabe erhaelt man eine klare Loesung, welche 15 Minuten bei -78°C nachgeruehrt wird. Im Anschluss daran wird das Kaeltebad entfernt und nach 40 Minuten die Loesung mit 100 ml 2N Salzsaeure auf pH 2 gestellt. Die Phasen werden getrennt, die organische Phase mit Wasser und gesaettigter Kochsalzloesung gewaschen und im Anschluss daran werden die Loesungsmittel unter Zusatz von 200 ml Wasser destillativ entfernt. Der ausgefallene Feststoff wird abfiltriert und getrocknet. Man erhaelt 25,8 g (91 percent) 4'-n-Pentoxy[1,1']biphenyl-4-boronsaeure vom Schmelzpunkt 148-150°C.
Reference: [1] Patent: EP1156997, 2004, B1, . Location in patent: Page 12
[2] Patent: US5516756, 1996, A,
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