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[ CAS No. 121554-18-5 ] {[proInfo.proName]}

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Chemical Structure| 121554-18-5
Chemical Structure| 121554-18-5
Structure of 121554-18-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 121554-18-5 ]

CAS No. :121554-18-5 MDL No. :MFCD07644474
Formula : C17H21BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QRZCEXCQSFQDMG-UHFFFAOYSA-N
M.W : 268.16 Pubchem ID :15458089
Synonyms :

Calculated chemistry of [ 121554-18-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.29
Num. rotatable bonds : 6
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 85.9
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 4.87
Log Po/w (WLOGP) : 2.77
Log Po/w (MLOGP) : 3.16
Log Po/w (SILICOS-IT) : 2.86
Consensus Log Po/w : 2.73

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.62
Solubility : 0.00645 mg/ml ; 0.0000241 mol/l
Class : Moderately soluble
Log S (Ali) : -5.45
Solubility : 0.000942 mg/ml ; 0.00000351 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.81
Solubility : 0.000413 mg/ml ; 0.00000154 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.4

Safety of [ 121554-18-5 ]

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 [ 121554-18-5 ]

* 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 [ 121554-18-5 ]
  • Downstream synthetic route of [ 121554-18-5 ]

[ 121554-18-5 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 63619-59-0 ]
  • [ 121554-18-5 ]
YieldReaction ConditionsOperation in experiment
78%
Stage #1: With iodine; magnesium In tetrahydrofuran for 3 h; Reflux
Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 1 h;
Stage #3: With hydrogenchloride In tetrahydrofuran
4'-Pentyl-4-biphenylboronic acid
4-Bromo-4'-pentylbiphenyl (3 g, 9.9 mmol) was added in one portion to Mg (0.27 g, 11.1 mmol), treated with I2, in THF (40 mL).
The mixture was heated at reflux for 3 h, cooled to -78 °C and trimethyl borate (2.06 g, 19.8 mmol) was added dropwise.
The mixture was warmed to room temperature over 1 h, acidified with HCl (2 M, 50 mL), extracted with Et2O (3 x 50 mL).
The combined ethereal washes were extracted with NaOH (100 mL, 1 M).
The aqueous phase was acidified with concentred HCl, extracted with Et2O (3 x 50 mL), dried (MgSO4) and the solvent removed under reduced to give the title compound (2.07 g, 78 percent) as an off white powder.
Reference: [1] Patent: EP2098520, 2009, A1, . Location in patent: Page/Page column 18
[2] Tetrahedron Letters, 2014, vol. 55, # 9, p. 1631 - 1634
  • 2
  • [ 5419-55-6 ]
  • [ 63619-59-0 ]
  • [ 121554-18-5 ]
YieldReaction ConditionsOperation in experiment
40%
Stage #1: With n-butyllithium In diethyl ether; hexane at -20 - 20℃; for 1.5 h; Argon atmosphere
Stage #2: at -20 - 20℃;
Stage #3: With hydrogenchloride In diethyl ether; hexane; water for 1 h;
[52.1] Into a flask purged with argon, 4-bromo-4'-n-pentylbiphenyl (5.0 g) and anhydrous ether (50 ml) were placed and cooled to -20°C. To the cooled solution, a 1.6 M hexane solution (15.2 ml) of n-butyllithium was slowly added dropwise. After 30 minutes, the temperature was elevated to the room temperature, and the mixture was stirred at the room temperature for 1 hour. The obtained reaction solution was added dropwise into an anhydrous ether solution (80 ml) of triisopropyl borate (8.28 g) at -20°C. The temperature was elevated to the room temperature, and the reaction solution was stirred for one night. To the resultant reaction solution, 2N hydrochloric acid was added, and the obtained mixture was stirred for 1 hour. The organic layer was separated and concentrated under a reduced pressure. The obtained solid was purified in accordance with the silica gel column chromatography (the solvent for elution: hexane/ethyl acetate = 3/1, 2/1 and 0/1 used in this order), and Compound 2 was obtained (the amount of the product: 1.77 g; the yield: 40percent). 1H-NMR (CDCl3) : δ (ppm) 8.3 (d, 1H), 7.9-7.5 (m, 6H), 7.3 (m, 1H), 4.6 (s, 2H), 2.6 (t, 2H), 1.8-1.2 (t, 6H), 0.9 (t, 3H)
Reference: [1] Patent: EP1440959, 2004, A1, . Location in patent: Page 23-24
  • 3
  • [ 688-71-1 ]
  • [ 63619-59-0 ]
  • [ 121554-18-5 ]
Reference: [1] Journal of Materials Chemistry C, 2014, vol. 2, # 5, p. 891 - 900
  • 4
  • [ 92-66-0 ]
  • [ 121554-18-5 ]
Reference: [1] Journal of Materials Chemistry C, 2014, vol. 2, # 5, p. 891 - 900
  • 5
  • [ 638-29-9 ]
  • [ 121554-18-5 ]
Reference: [1] Journal of Materials Chemistry C, 2014, vol. 2, # 5, p. 891 - 900
  • 6
  • [ 63619-55-6 ]
  • [ 121554-18-5 ]
Reference: [1] Journal of Materials Chemistry C, 2014, vol. 2, # 5, p. 891 - 900
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