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[ CAS No. 5122-94-1 ] {[proInfo.proName]}

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Chemical Structure| 5122-94-1
Chemical Structure| 5122-94-1
Structure of 5122-94-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5122-94-1 ]

CAS No. :5122-94-1 MDL No. :MFCD00093311
Formula : C12H11BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :XPEIJWZLPWNNOK-UHFFFAOYSA-N
M.W :198.03 Pubchem ID :151253
Synonyms :

Calculated chemistry of [ 5122-94-1 ]

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 : 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 : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.45
Log Po/w (WLOGP) : 1.03
Log Po/w (MLOGP) : 1.88
Log Po/w (SILICOS-IT) : 0.9
Consensus Log Po/w : 1.25

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.07
Solubility : 0.168 mg/ml ; 0.000849 mol/l
Class : Soluble
Log S (Ali) : -2.94
Solubility : 0.226 mg/ml ; 0.00114 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.81
Solubility : 0.0307 mg/ml ; 0.000155 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.92

Safety of [ 5122-94-1 ]

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 [ 5122-94-1 ]

* 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 [ 5122-94-1 ]
  • Downstream synthetic route of [ 5122-94-1 ]

[ 5122-94-1 ] Synthesis Path-Upstream   1~19

  • 1
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YieldReaction ConditionsOperation in experiment
84%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5 h; Inert atmosphere
Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 4.5 h;
Stage #3: With water In tetrahydrofuran; hexane; ethyl acetate
4-bromobiphenyl (30g, 0.12mop was added to a one-neck flask and an argon atmosphere was established in a vacuum. Tetrahydinfuran (THA) (SOOmI) was added and the mixture was stirred at -7KC for 10 minutes. After adding mBuLi(2.SM in hexane) (77mL, 0.19moL), the mixture was stiu-a3 for I hour and 30 minutes at -7RC. Then, nimethyl borate (21.9m1, 0. 9mol) was added at-78C After sorting the mixture for 30 minutes at-78C, the mixture was stirred at room temperature for 4 hours. After the reaction was completed, extraction was performed using distilled water and ethyl acetate (EA). The organic layer was dried with MgSO, and the solvent was removed using a rotary evaporator. Pure Compound A (21g 84percent) was separated by column chromatography using hexane and EA as an eluent.
Reference: [1] Patent: WO2011/105700, 2011, A1, . Location in patent: Page/Page column 18; 19; 21; 22
[2] Angewandte Chemie - International Edition, 2006, vol. 45, # 9, p. 1404 - 1408
[3] Tetrahedron, 2007, vol. 63, # 20, p. 4297 - 4303
[4] Journal of Organic Chemistry, 2011, vol. 76, # 4, p. 1013 - 1030
[5] Journal of the Chemical Society [Section] C: Organic, 1966, p. 566 - 571
[6] European Journal of Organic Chemistry, 2000, # 20, p. 3393 - 3397
[7] Journal of Physical Chemistry B, 2000, vol. 104, # 49, p. 11680 - 11688
[8] Heterocycles, 2002, vol. 57, # 5, p. 871 - 879
[9] Angewandte Chemie - International Edition, 2008, vol. 47, # 6, p. 1115 - 1118
[10] Patent: WO2007/86695, 2007, A1, . Location in patent: Page/Page column 62
[11] Journal of Organic Chemistry, 2013, vol. 78, # 13, p. 6427 - 6439
[12] Patent: KR2017/49296, 2017, A,
[13] ChemCatChem, 2018, vol. 10, # 19, p. 4253 - 4257
  • 2
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YieldReaction ConditionsOperation in experiment
74%
Stage #1: With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5 h;
Stage #2: at -78 - 20℃;
Sub 2-1 (4) (4.66g, 20mmol) dissolved in anhydrous Ether, a reaction temperature of-78 ° C to a lower, n-BuLi (2.5M in hexane) (1.4g, 22mmol) was slowly addeddropwise, and I then, the reaction is stirred for 30 minutes. After the dropwise additionTriisopropyl borate (5.64g, 30mmol) lowering the temperature of the reaction back to -78 ° C. Stirring at room temperature, diluted with water and it binds the 2N HCl. Aftercompletion of reaction, ethyl acetate and water, dried over MgSO4 and the organic layerwas extracted and concentrated and to the resulting organic silicagel column andrecrystallized to give 2.93g of Sub 2 (4). (Yield: 74percent)
90% With n-butyllithium In tetrahydrofuran To a solution of 4-bromobiphenyl (2.00 g, 8.58 mmol) in THF (20 mL) at -78° C. was added n-butyllithium (4.0 mL of 2.5 M in hexanes) in a slow stream via syringe.
After 15 minutes, triisopropylborate (3.0 mL, 13 mmol) was added in a slow stream via syringe.
After 10 minutes, the resultant homogeneous solution was allowed to warm to ambient temperature over 45 minutes and partitioned between EtOAc (50 mL) and 10percent aqueous HCI (50 mL).
The aqueous layer was separated and extracted with more EtOAc.
The combined organic layers were washed with brine, dried over Na2 SO4 and concentrated to give a crude product which was triturated with hexanes to yield 1.53 g (90percent) of 4-biphenylboronic acid as a white solid. 1 H NMR (DMSO-d6): δ 8.05 (s, 2H), 7.83 (d, 2H, J=8.5 Hz), 7.65 (d, 2H, J=7.0 Hz), 7.60 (d, 2H, J=8.1 Hz), 7.43 (t, 2H, J=7.4 Hz), 7.33 (t, 1H, J=7.2 Hz). Anal. C12 H11 BO2: C, 72.78; H, 560. Found: C, 72.51; H, 5.62.
Reference: [1] Patent: KR2015/121394, 2015, A, . Location in patent: Paragraph 0271-0275
[2] Patent: US6008243, 1999, A,
  • 3
  • [ 98-80-6 ]
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YieldReaction ConditionsOperation in experiment
86% With potassium carbonate In ethanol; water at 50℃; for 5 h; Inert atmosphere Under a nitrogen gas atmosphere, Phenylboronic acid150 mg (1.23 mmol)324 mg (0.55 mmol) of potassium salt of stable art type complex of 4-bromophenylboronic acid and scyllo-inositol (0.55 mmol) of potassium salt of scyllo-inositol and 340 mg (2.46 mmol) of potassium carbonate were dissolved in degassed ethanol: 1) mixed solvent, and a catalyst solution prepared by suspending 8 mg (0.012 mmol) of triphenylphosphine ligand-palladium in 1 mL of a mixed solvent of ethanol: water (5: 1) was added thereto , And the cross-coupling reaction was started by stirring at a reaction temperature of 50 ° C. After 5 hours of reaction, the reaction solvent was distilled off under reduced pressure to stop the reaction. 15 ml of water and 10 ml of ethyl acetate were added to the residue and dissolved / extracted, and the obtained suspension was filtered to remove the insoluble catalyst. Further, an ethyl acetate layer and an aqueous layer were separated, and the aqueous layer was further washed with a small amount of ethyl acetate. The aqueous layer was taken out and hydrochloric acid was added so that the pH became 2 to 3, the scyllo-inositol complex dissociated and the deprotection reaction progressed. The arylboronic acid was insolubilized with deprotection in an acidic aqueous solution. Thereto, 15 ml of ethyl acetate was added to extract the arylboronic acid, and the mixture was separated to obtain an ethyl acetate layer. The aqueous layer was again extracted with 10 ml of ethyl acetate, combined with the first ethyl acetate solution, dried with anhydrous Na 2 SO 4 and concentrated. The precipitated solid was purified by silica gel column chromatography to obtain 187 mg (0.95 mmol) of biphenyl 4-boronic acid (yield: 86percent).
Reference: [1] Patent: JP6068194, 2017, B2, . Location in patent: Paragraph 0167; 0168
  • 4
  • [ 67-56-1 ]
  • [ 55124-35-1 ]
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YieldReaction ConditionsOperation in experiment
78%
Stage #1: With magnesium; phenylmagnesium bromide In tetrahydrofuran at 20℃; for 0.166667 h;
Stage #2: at 70℃;
General procedure: To a solution in THF (4 mL) of DIPAB (863 mg, 7.5 mmol) and Mg (182 mg, 7.5 mmol) were added a PhMgBr 1M THF solution (375 μL, 375μmol) at room temperature. After 10 min, 30 mL of anhydrous THF were added followed by the arylbromide (5 mmol). The reaction mixture was cooled down to 0 °C and quenched slowly with 7 mL of MeOH. After 1h, volatile were removed under reduced pressure and the resulting solid was dissolved in 1N HCl/MeOH (7/3). After 1h at room temperature, 100 mL of AcOEt were added, the organic phase was washed with 1N HCl (30 mL) and brine (3×30 mL). Organic phases were concentrated under reduced pressure yielding a solid which was recrystallized from H2O.
Reference: [1] Tetrahedron, 2019, vol. 75, # 2, p. 164 - 171
  • 5
  • [ 121-43-7 ]
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Reference: [1] Journal of Physical Chemistry B, 2001, vol. 105, # 37, p. 8845 - 8860
[2] Journal of Physical Chemistry B, 2001, vol. 105, # 37, p. 8845 - 8860
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 13, p. 1733 - 1738
  • 6
  • [ 98-80-6 ]
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Reference: [1] Organic Letters, 2015, vol. 17, # 24, p. 6030 - 6033
  • 7
  • [ 7732-18-5 ]
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YieldReaction ConditionsOperation in experiment
1.82 g With hydrogenchloride In tetrahydrofuran for 0.5 h; Inert atmosphere Under nitrogen, 2.33 g (10 mmol) of 4-bromo-1,1'-biphenyl was dissolved in 40 ml of anhydrous THF, the temperature of the reaction was lowered to -78 ° C, After slowly adding 4 ml of 2.5 M n-BuLi dropwise, the reaction was stirred at 0 ° C for 1 hour. Then, the temperature of the reaction After lowering to -78 deg. C, 12.47 g (12 mmol) of trimethylborate was added dropwise, and the mixture was stirred at room temperature for 12 hours. The reaction After completion of the reaction, 2N-HCl aqueous solution was added, stirred for 30 minutes, and extracted with ether. Water in the organic layer was removed with anhydrous MgSO 4, filtered under reduced pressure, and the organic solvent was concentrated to obtain the resulting compound in a ratio of Hex: MC = 6: 1 to obtain 1.82 g (92percent) of
Reference: [1] Patent: KR2017/49296, 2017, A, . Location in patent: Paragraph 0184; 0185; 0186; 0187; 0188
  • 8
  • [ 1104636-67-0 ]
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Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 24, p. 8951 - 8964
  • 9
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Reference: [1] Chinese Journal of Chemistry, 2017, vol. 35, # 4, p. 429 - 434
  • 10
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Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 24, p. 8951 - 8964
  • 11
  • [ 150-46-9 ]
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Reference: [1] Organic Letters, 1999, vol. 1, # 13, p. 2093 - 2096
  • 12
  • [ 688-74-4 ]
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Reference: [1] Journal of the American Chemical Society, 1934, vol. 56, p. 1850,1856
  • 13
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Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 13, p. 4769 - 4779
  • 14
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Reference: [1] ChemCatChem, 2018, vol. 10, # 19, p. 4253 - 4257
  • 15
  • [ 24388-23-6 ]
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Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 24, p. 8951 - 8964
  • 16
  • [ 105123-35-1 ]
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Reference: [1] Heterocycles, 2002, vol. 57, # 5, p. 787 - 790
  • 17
  • [ 1591-31-7 ]
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Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1975, vol. 45, p. 773 - 776[2] Zhurnal Obshchei Khimii, 1975, vol. 45, p. 786 - 789
  • 18
  • [ 5122-94-1 ]
  • [ 73852-88-7 ]
  • [ 1080632-76-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 19, p. 9056 - 9064
  • 19
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  • [ 1080632-76-3 ]
Reference: [1] Patent: KR2015/117173, 2015, A,
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