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[ CAS No. 1402238-32-7 ] {[proInfo.proName]}

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Chemical Structure| 1402238-32-7
Chemical Structure| 1402238-32-7
Structure of 1402238-32-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1402238-32-7 ]

CAS No. :1402238-32-7 MDL No. :MFCD18311840
Formula : C12H10BFO3 Boiling Point : -
Linear Structure Formula :- InChI Key :IQNYGJLCROJQSI-UHFFFAOYSA-N
M.W : 232.02 Pubchem ID :53216533
Synonyms :

Calculated chemistry of [ 1402238-32-7 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 62.74
TPSA : 49.69 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.46
Log Po/w (WLOGP) : 1.72
Log Po/w (MLOGP) : 1.94
Log Po/w (SILICOS-IT) : 0.83
Consensus Log Po/w : 1.39

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.15
Solubility : 0.163 mg/ml ; 0.000704 mol/l
Class : Soluble
Log S (Ali) : -3.15
Solubility : 0.165 mg/ml ; 0.000712 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.83
Solubility : 0.0342 mg/ml ; 0.000147 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.24

Safety of [ 1402238-32-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1402238-32-7 ]

* 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 [ 1402238-32-7 ]
  • Downstream synthetic route of [ 1402238-32-7 ]

[ 1402238-32-7 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 5419-55-6 ]
  • [ 851199-57-0 ]
  • [ 1402238-32-7 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With n-butyllithium In tetrahydrofuran; water at -78 - 20℃; for 0.166667 h; Inert atmosphere
Step 4Into a 300 mL 3-necked round-bottom flask purged and maintained under an inert atmosphere of nitrogen, was placed a solution of l-(2-fluorophenoxy)-4-iodobenzene (3.3 g, 30.51 mmol, 1.00 equiv) in tetrahydrofuran (50 mL). n-BuLi (4.4 mL) was added dropwise with stirring at -78 °C. The resulting solution was stirred for 10 mins at -78°C and then tris(propan-2-yl)borate (2.1 g, 1 3.17 mmol, 1.06 equiv) was added dropwise with stirring at - 78 °C over 30 min. The resulting solution was stirred while the temperature warmed from -78 °C to room temperature. The reaction was then quenched by the addition of saturated aqueous NII4CI and concentrated under vacuum. The resulting solution was diluted with 30percent aquious potassium hydroxide and then washed with ether. The pH of the aqueous was adjusted to 2-4 with hydrogen chloride (37percent ). The resulting solution was extracted with ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum to give 2,2 g (90percent) of [4-(2-fSuorophenoxy)phenyl]boronic acid as a white solid
90%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 0.166667 h;
Step 4
Into a 100 mL 3-necked round-bottom flask purged and maintained under an inert atmosphere of nitrogen, was placed a solution of 1-(2-fluorophenoxy)-4-iodobenzene (3.3 g, 10.51 mmol, 1.00 equiv) in tetrahydrofuran (50 mL).
n-BuLi (4.4 mL) was added dropwise with stirring at -78° C.
The resulting solution was stirred for 10 mins at -78° C. and then tris(propan-2-yl)borate (2.1 g, 11.17 mmol, 1.06 equiv) was added dropwise with stirring at -78° C. over 10 min.
The resulting solution was stirred while the temperature warmed from -78° C. to room temperature.
The reaction was then quenched by the addition of saturated aqueous NH4Cl and concentrated under vacuum.
The resulting solution was diluted with 10percent aquious potassium hydroxide and then washed with ether.
The pH of the aqueous was adjusted to 2-4 with hydrogen chloride (37percent).
The resulting solution was extracted with ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum to give 2.2 g (90percent) of [4-(2-fluorophenoxy)phenyl]boronic acid as a white solid
Reference: [1] Patent: WO2012/158764, 2012, A1, . Location in patent: Page/Page column 204-205
[2] Patent: US8673925, 2014, B1, . Location in patent: Page/Page column 232
  • 2
  • [ 851199-57-0 ]
  • [ 1402238-32-7 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667 h; Inert atmosphere
Stage #2: With Triisopropyl borate In tetrahydrofuran at -78 - 20℃; for 0.166667 h; Inert atmosphere
Stage #3: With water; ammonium chloride In tetrahydrofuran
Step 4. Into a 100 mL 3-necked round-bottom flask purged and maintained under an inert atmosphere of nitrogen, was placed a solution of 1-(2-fluorophenoxy)-4-iodobenzene (3.3 g,10.51 mmol, 1.00 equiv) in tetrahydrofuran (50 mL). n-BuLi (4.4 mL) was added dropwise with stirring at -78 °C. The resulting solution was stirred for 10 mins at -78 °C and then tris(propan-2-yl)borate (2.1 g, 11.17 mmol, 1.06 equiv) was added dropwise with stirring at78 °C over 10 mm. The resulting solution was stirred while the temperature warmed from -78°C to room temperature. The reaction was then quenched by the addition of saturated aqueous NH4Cl and concentrated under vacuum. The resulting solution was diluted with 10percent aqueous potassium hydroxide and then washed with ether. The pH of the aqueous was adjusted to 2-4 with hydrogen chloride (37percent ). The resulting solution was extracted with ethyl acetate andthe organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum to give 2.2 g (90percent) of [4-(2-fluorophenoxy)phenyl]boronic acid as a white solid.
Reference: [1] Patent: WO2014/22569, 2014, A1, . Location in patent: Page/Page column 85
  • 3
  • [ 5419-55-6 ]
  • [ 1402238-32-7 ]
YieldReaction ConditionsOperation in experiment
11%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at 20℃; for 6 h;
To a solution of I -(4-bromophenoxy)-2-lluoroben2ene (10 g, 37.4 mmoi), in tetrahydtx>furan (150 mL) at -78 "C was added n-batyllithium (2,5 M, 22.4 mL, 56,2 mmol) and th reaction mixture was stirred at that temperature- for 1 hour. Triisopropyl borate ( 10.3 g, 44,9 mmol) was then added and the reaction was allowed to warm up to room temperature with stirring for 6 hours. The reaction mixture was then quenched with a saturated .solution of ammonium chloride and concentrated under reduced pressure. The resultant residue was diluted with an aqueous solution of 3 percent KOH and neutral ized to pH 2-3 with dilute HQ. The resulting solution was extracted with ethyl acetate and the combined extracts were dried over anhydrous NiS(. filtered and evaporated in. vacuo to afford a crude compound which was purified by flash chromatography on silica gel ( 100-200 mesh) eluting with 40percent ethyl acetate in hexanes to afford the title compound as art off white solid i'2,6 g, 1 1 ' ). - NMR (CDt, 400 MHz) 6 8. 1 (d, / = S.6 Hz, 2H), 7.20 (m, 4H), 7.06 id, J = 8.6 Hz, 2H).
Reference: [1] Patent: WO2018/49127, 2018, A1, . Location in patent: Page/Page column 108
  • 4
  • [ 367-12-4 ]
  • [ 1402238-32-7 ]
Reference: [1] Patent: WO2012/158764, 2012, A1,
[2] Patent: WO2014/22569, 2014, A1,
[3] Patent: US8673925, 2014, B1,
  • 5
  • [ 350-46-9 ]
  • [ 1402238-32-7 ]
Reference: [1] Patent: WO2012/158764, 2012, A1,
[2] Patent: WO2014/22569, 2014, A1,
[3] Patent: US8673925, 2014, B1,
  • 6
  • [ 305801-12-1 ]
  • [ 1402238-32-7 ]
Reference: [1] Patent: WO2012/158764, 2012, A1,
[2] Patent: WO2014/22569, 2014, A1,
[3] Patent: US8673925, 2014, B1,
  • 7
  • [ 1478-03-1 ]
  • [ 1402238-32-7 ]
Reference: [1] Patent: WO2012/158764, 2012, A1,
[2] Patent: WO2014/22569, 2014, A1,
[3] Patent: US8673925, 2014, B1,
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