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Chemical Structure| 4688-76-0 Chemical Structure| 4688-76-0

Structure of 2-Biphenylboronic acid
CAS No.: 4688-76-0

Chemical Structure| 4688-76-0

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Product Details of [ 4688-76-0 ]

CAS No. :4688-76-0
Formula : C12H11BO2
M.W : 198.03
SMILES Code : C1=C(C(=CC=C1)B(O)O)C2=CC=CC=C2
MDL No. :MFCD00136929
InChI Key :HYCYKHYFIWHGEX-UHFFFAOYSA-N
Pubchem ID :4589187

Safety of [ 4688-76-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 4688-76-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 61.7
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

40.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.45
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.03
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.88
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.9
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.25

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.07
Solubility 0.168 mg/ml ; 0.000849 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.94
Solubility 0.226 mg/ml ; 0.00114 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.81
Solubility 0.0307 mg/ml ; 0.000155 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.77 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.87

Application In Synthesis of [ 4688-76-0 ]

* 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.

  • Downstream synthetic route of [ 4688-76-0 ]

[ 4688-76-0 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 16932-45-9 ]
  • [ 4688-76-0 ]
  • [ 223268-67-5 ]
  • 2
  • [ 7051-15-2 ]
  • [ 4688-76-0 ]
  • [ 223268-67-5 ]
  • 3
  • [ 104-21-2 ]
  • [ 4688-76-0 ]
  • 2-(4-methoxybenzyl)-1,1'-biphenyl [ No CAS ]
  • 4
  • [ 109179-31-9 ]
  • [ 4688-76-0 ]
  • 3-methyl-2-(2-phenylphenyl)benzaldehyde [ No CAS ]
  • 5
  • [ 4688-76-0 ]
  • [ 33332-28-4 ]
  • [ 1454654-41-1 ]
YieldReaction ConditionsOperation in experiment
63.02% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In ethanol; toluene; at 130℃; for 1h;Microwave irradiation; 6-biphenyl-2- l-pyrazin-2-ylamine To a solution of 2-amino-6-chloro-pyrazine (0.25 g, 1.93 mmol) in toluene / ethanol (9:1 , 10 ml), 2-biphenyl boronic acid (0.42 g, 2.13 mmol), tetrakis(triphenylphosphine)palladium(0) (0.067 g, 0.05 mmol) and cesium carbonate (1.25 g, 3.87 mmol) are added, degassed briefly and irradiated in microwave at 130 °C for an hour. The reaction mixture is passed through celite, washed with dichloromethane/methanol (1 :1 , 25 ml), the filtrate is concentrated and purified by silica column using (230-400) mesh to get the product as yellow solid (0.3 g, 63.02 percent); TLC: chloroform/methanol (9.5/0.5) Rf - 0.3. 1H NMR: 400 MHz, DMSO-d6: delta [ppm] 7.68 (s, 1 H), 7.58-7.55 (m, 1 H), 7.44- 7.51 (m, 2H), 7.39-7.41 (m, 1 H), 7.23-7.32 (m, 3H), 7.12-7.15 (m, 3H), 6.42 (br s, 2H); LCMS: Mass found (M+, 248.3) Method: A-0.1 percent TFA in H20, B-0.1percent TFA in ACN: Flow - 0.6 ml/min. Column: XBridge C8 (50 X 4.6 mm, 3.5 pm), +ve mode Rt (min): 3.54 area percent -98.72 (Max).
  • 6
  • [ 1333240-17-7 ]
  • [ 4688-76-0 ]
  • 2-(2-biphenyl)-4,5-dimethoxypyrimidine [ No CAS ]
  • 7
  • [ 4688-76-0 ]
  • [ 57103-20-5 ]
  • 3-(biphenyl-2-yl)-6-bromo-9-phenyl-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% In ethanol; toluene; Example 3 Synthesis of 3-(biphenyl-2-yl)-6-bromo-9-phenyl-9H-carbazole A mixture of 40.1 g (100 mmol) of <strong>[57103-20-5]3,6-dibromo-9-phenyl-9H-carbazole</strong>, 21.8 g (110 mmol) of biphenyl-2-ylboronic acid, 2.31 g (2 mmol) of Pd(PPh3)4, 75 ml of 2M Na2CO3, 150 ml of EtOH and 300 ml toluene was degassed and placed under nitrogen, and then heated at 100° C. for 12 h. After finishing the reaction, the mixture was allowed to cool to room temperature. The organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica to give product (19.9 g, 42.0 mmol, 42percent) as a white solid.
  • 8
  • [ 36023-06-0 ]
  • [ 4688-76-0 ]
  • (±)-8-(biphenyl-2-yl)-7-methoxyquinoline [ No CAS ]
  • 9
  • [ 1097884-37-1 ]
  • [ 4688-76-0 ]
  • C30H21N [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 100℃; for 12h; A 2 L reactor was charged with [Intermediate 1-a] (52 g, 177 mmol) 2-Biphenylboronic acid (42 g, 212 mmol),Tetrakis (triphenylphosphine) palladium (4.1 g, 3.5 mmol),Potassium carbonate (73.4 g, 531 mmol), toluene (600 mL) and distilled water (200 mL) were added, and the mixture was stirred at 100 C for 12 hours.After cooling to room temperature, the organic layer was extracted with ethyl acetate.The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain [intermediate 1-b]. (41 g, 72%). In Synthesis Example 1- (2)Except that [Intermediate 8-a] was used instead of [Intermediate 1-a] Synthesized in the same manner [Intermediate 8-b] was obtained. (57 g, 68%).
  • 10
  • [ 50548-45-3 ]
  • [ 4688-76-0 ]
  • C24H16O [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 100℃; for 12h; A 2 L reactor was charged with [Intermediate 1-a] (52 g, 177 mmol) 2-Biphenylboronic acid (42 g, 212 mmol),Tetrakis (triphenylphosphine) palladium (4.1 g, 3.5 mmol),Potassium carbonate (73.4 g, 531 mmol), toluene (600 mL) and distilled water (200 mL) were added, and the mixture was stirred at 100 ° C for 12 hours.After cooling to room temperature, the organic layer was extracted with ethyl acetate.The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain [intermediate 1-b]. (41 g, 72percent). <strong>[50548-45-3]1-bromodibenzofuran</strong> was used instead of [Intermediate 1-a] used in the above Synthesis Example 1- (2) Was synthesized in the same manner as in [Intermediate 4-a]. (57 g, 68percent).
  • 11
  • [ 4688-76-0 ]
  • [ 16657-07-1 ]
  • 4-([1,1′-biphenyl]-2-yl)-1H-indene [ No CAS ]
YieldReaction ConditionsOperation in experiment
5.383 g With trans-bis(triphenylphosphine)palladium dichloride; potassium carbonate; In 1,4-dioxane; water; at 80℃; for 6h;Inert atmosphere; To a nitrogen-purged solution of 245 <strong>[16657-07-1]7-bromo-indene</strong> (7.366 g, 37.76 mmol) in 246 1,4-dioxane (60 mL) and 247 water (20 mL), 248 2-biphenylboronic acid (14.96 g, 75.55 mmol, 2.00 eq), 249 potassium carbonate (16.17 g, 115.35 mmol, 3.05 eq), and 250 trans-dichlorobis(triphenylphosphine)palladium(II) (1.394 g, 1.986 mmol, 0.05 eq) were added with additional water (10 mL). The reaction was stirred and heated to 80 C. for 6h. The reaction was allowed to cool to room temperature. The reaction was poured into water (200 mL) and extracted with ethyl acetate. The combined ethyl acetate extracts were washed with brine and dried over sodium sulfate. The mixture was filtered, and the filtrate was concentrated in vacuo to give a dark brown oil. The oil was purified via silica gel column chromatography to afford the 251 product (5.383 g).
 

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