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[ CAS No. 870774-25-7 ] {[proInfo.proName]}

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Chemical Structure| 870774-25-7
Chemical Structure| 870774-25-7
Structure of 870774-25-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 870774-25-7 ]

CAS No. :870774-25-7 MDL No. :MFCD08669639
Formula : C16H13BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BQHVXFQXTOIMQM-UHFFFAOYSA-N
M.W : 248.08 Pubchem ID :44119399
Synonyms :

Calculated chemistry of [ 870774-25-7 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 79.21
TPSA : 40.46 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) : -5.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.7
Log Po/w (WLOGP) : 2.19
Log Po/w (MLOGP) : 2.72
Log Po/w (SILICOS-IT) : 1.93
Consensus Log Po/w : 2.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.2
Solubility : 0.0156 mg/ml ; 0.0000631 mol/l
Class : Moderately soluble
Log S (Ali) : -4.24
Solubility : 0.0143 mg/ml ; 0.0000575 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.49
Solubility : 0.00081 mg/ml ; 0.00000327 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.16

Safety of [ 870774-25-7 ]

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 [ 870774-25-7 ]

* 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 [ 870774-25-7 ]
  • Downstream synthetic route of [ 870774-25-7 ]

[ 870774-25-7 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 204530-94-9 ]
  • [ 870774-25-7 ]
YieldReaction ConditionsOperation in experiment
67%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -60℃; for 2 h; Inert atmosphere
Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -60 - 20℃; for 17 h; Inert atmosphere
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water at 20℃; for 1 h;
Under an argon gas atmosphere, a mixture of 208.8 g (737.4 mmol) of 1-(4-bromophenyl)naphthalene and 2.1 L of dehydrated TI-IF was cooled down to minus 60 degree C. Then, 567 ml (884.9 mmol) of hexane solution of 1.56M n-butyllithium was dropped into the mixture while the mixture was being stirred. The reaction mixture was further stirred at minus 60 degrees for 2 hours. 416 g (2.21 mol) of triisopropylborate was dropped into the reaction mixture at minus 60 degrees C. The reaction mixture was then stirred at room temperature for 17 hours. The reaction mixture was added with aqueous solution of hydrochloric acid and stirred at room temperature for 1 hour. After the reaction, the reaction mixture was added with toluene, and aqueous phase thereof was eliminated. Then, organic phase thereof was dried with magnesium sulfate, and the solvent was distilled away under reduced pressure. By recrystallizing the obtained solid by toluene, 126 g of 4-(1-naphthyl)phenylboronic acid was obtained at an yield of 67percent.
Reference: [1] Patent: US2010/331585, 2010, A1, . Location in patent: Page/Page column 96-97
  • 2
  • [ 5419-55-6 ]
  • [ 204530-94-9 ]
  • [ 870774-25-7 ]
YieldReaction ConditionsOperation in experiment
67% With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane; toluene (8)
Synthesis of Compound 2-8
Under an argon gas atmosphere, a mixture of 208.8 g (737.4 mmol) of 1-(4-bromophenyl) naphthalene and 2.1 L of dehydrated THF was cooled down to -60 degrees C., and added with 567 mL (884.9 mmol) of hexane solution of 1.56M n-butyllithium in drops while being stirred.
Then, the reaction mixture was stirred for two hours at -60 degree C. 416 g (2.21 mol) of triisopropyl borate was dropped into the reaction solution at -60 degrees C. Subsequently, the reaction mixture was stirred for 17 hours at room temperature.
The reaction mixture was further added with solution of hydrochloric acid to be stirred for one hour at room temperature.
After the reaction, the reaction mixture was further added with toluene, so that aqueous phase thereof was eliminated.
After organic phase thereof was dried with magnesium sulfate, the solvent was distilled away under reduced pressure.
By recrystallizing the obtained solid by toluene, 126 g of 4-(1-naphthyl) phenylboronic acid was obtained at an yield of 67percent.
Reference: [1] Patent: US2009/8605, 2009, A1,
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