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[ CAS No. 656235-44-8 ] {[proInfo.proName]}

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Chemical Structure| 656235-44-8
Chemical Structure| 656235-44-8
Structure of 656235-44-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 656235-44-8 ]

CAS No. :656235-44-8 MDL No. :MFCD09033623
Formula : C7H5BFNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :PPLSIVNRHUSMMC-UHFFFAOYSA-N
M.W : 164.93 Pubchem ID :12118997
Synonyms :

Calculated chemistry of [ 656235-44-8 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.94
TPSA : 64.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.65
Log Po/w (WLOGP) : -0.2
Log Po/w (MLOGP) : 0.08
Log Po/w (SILICOS-IT) : -0.34
Consensus Log Po/w : 0.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.58
Solubility : 4.38 mg/ml ; 0.0265 mol/l
Class : Very soluble
Log S (Ali) : -1.57
Solubility : 4.39 mg/ml ; 0.0266 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.65
Solubility : 3.74 mg/ml ; 0.0226 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.99

Safety of [ 656235-44-8 ]

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 [ 656235-44-8 ]

* 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 [ 656235-44-8 ]
  • Downstream synthetic route of [ 656235-44-8 ]

[ 656235-44-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 403-54-3 ]
  • [ 656235-44-8 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With Triisopropyl borate; lithium diisopropyl amide In tetrahydrofuran; hexane at -50 - -5℃; for 1.5 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; hexane; tert-butyl methyl ether at 20℃; for 0.5 h;
Intermediate 6; ψ-Cvano^-fluorophenylboronic acid; A 500 mL 3-neck, round bottom flask, equipped with a magnetic stirring bar, addition funnel, and nitrogen gas inlet, was charged with 3-fluorobenzonitrile (10.0 g, 82.56 mmol), triisopropyl borate (28.5 mL, 23.3 g, 123.84 mmol), and 100 mL of anhydrous THF. The mixture was cooled to -50 0C under nitrogen and a solution of LDA in THF/hexane (86.7 mmol, freshly prepared from 8.77 g of diisopropylamine in 20 mL of THF and 54.2 mL of a 1.6 M solution of n-BuLi in hexane) was added dropwise over a period of 1 h. The mixture was warmed to -5 0C and stirred for 30 min. Then 70 mL of 5 N HCIaq and 50 mL of MTBE was added and stirred for 30 min at room temperature. The mixture was extracted with MTBE (4x100 mL), the MTBE extract was washed with brine (2x100 mL), evaporated under reduced pressure keeping the temperature below 20 0C, and dried under vacuum at room temperature to give 12.16 g (89 percent) of δ-cyano^-fluorophenylboronic acid as a white solid. LCMS m/z (M+H)+: 165.8. 1H NMR (300 MHz, DMSO-d6): δ 8.92 (2H), 7.65 (1H), 7.57 (1H), 7.49 (1H).
Reference: [1] Patent: WO2006/51410, 2006, A1, . Location in patent: Page/Page column 44
[2] Journal of Organic Chemistry, 2005, vol. 70, # 15, p. 5938 - 5945
[3] Journal of Organic Chemistry, 2004, vol. 69, # 2, p. 566 - 569
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